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Exam Questions + Alpha Carbon Chemistry Enols And + Ch.21

Organic Chemistry, 4e (Klein)

Chapter 21 Alpha Carbon Chemistry: Enols and Enolates

1) Which one of the compounds shown is most acidic?

A) ethyl acetoacetate

B) 2-butanone

C) ethyl pentanoate

D) 1-butanol

E) 3-pentanone

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

2) How many alpha hydrogens are in 2-pentanone?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 1

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

3) How many beta hydrogens are in 2-pentanone?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 1

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

4) How many gamma hydrogens are in 2-pentanone?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 1

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

5) Which of the indicated α-hydrogens is most acidic?

The fourth molecular structure shows C H 3 C H 2 C (double bond O) O C H 2 C H 3. An arrow points to the second C H 2 group. The fifth molecular structure shows C H 3 C H 2 C (double bond O) C H 2 C H 3. An arrow points to the second C H 2 group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

6) Which is the most acidic hydrogen in the compound shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

7) Which is the most acidic hydrogen in the compound shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

8) Which is the most acidic hydrogen in the compound shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

9) Which carbon atom has the most acidic hydrogen in the compound shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

10) Which one of the indicated hydrogens is the most acidic?

The fourth structure shows Methyl 2,6-dioxocyclohexanecarboxylate with SMILES string COC(=O)C1C(=O)CCCC1=O. A hydrogen atom is bonded the second carbon atom. The fifth structure shows cyclohexane with SMILES string C1CCCCC1. A hydrogen atom is bonded to the first carbon atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

11) Arrange the indicated hydrogens in decreasing order (most to least) of acidity.

A) I > II > III > IV

B) IV > II > III > I

C) III > II > I > IV

D) II > I > III > IV

E) III > I > II > IV

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

12) Which of the choice(s) shows a keto-enol tautomeric pair(s)?

Two equilibrium reactions are shown. The reactant in the first equilibrium reaction has molecular formula C H 3 C H = C (O negative) H. The product has molecular structure C H 3 C (negative) H C (=O) H. The reactant in the second equilibrium reaction has molecular formula C H 3 C (O H) = C H 2. The product has molecular formula C H 3 C (=O) C H 3.

An equilibrium reaction numbered 3 is shown. The reactant has molecular formula C H 3 C (O negative) = C H 2. The product has molecular formula C H 3 C (=O) C (negative) H 2.

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

13) Which of the choices is a keto-enol tautomeric pair?

Two equilibrium reactions are shown. The equilibrium reaction numbered 1 shows cyclohexanone with SMILES string C1CCC(=O)CC1 form cyclohexanol with SMILES string C1CCC(CC1)O. The equilibrium reaction numbered 2 shows cyclohexanone with SMILES string C1CCC(=O)CC1 form 2-Cyclohexen-1-ol with SMILES string C1CC=CC(C1)O.

The equilibrium reaction number 5 shows cyclohexanone with SMILES string C1CCC(=O)CC1 form a product with SMILES string [OH+]=C1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

14) Which of the choices is a keto-enol tautomeric pair?

An equilibrium reaction numbered 1 shows Octahydro-2(1H)-naphthalenone with SMILES string C1CCC2CC(=O)CCC2C1 form 3,4,4a,5,6,7,8,8a-Octahydro-2-naphthalenol with SMILES string OC1CCC2CCCCC2C=1.

An equilibrium reaction numbered 2 shows Octahydro-2(1H)-naphthalenone with SMILES string C1CCC2CC(=O)CCC2C1 form a product with SMILES string OC2CCC1CC=CCC1C2.

An equilibrium reaction numbered 3 shows Octahydro-2(1H)-naphthalenone with SMILES string C1CCC2CC(=O)CCC2C1 form a product with SMILES string OC2CCC1CCC=CC1C2.

An equilibrium reaction numbered 4 shows Octahydro-2(1H)-naphthalenone with SMILES string C1CCC2CC(=O)CCC2C1 form (2R,4aS,8aR)-1,2,4a,5,6,7,8,8a-Octahydro-2-naphthalenol with SMILES string OC2C=CC1CCCCC1C2.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

15) Which one of the compounds shown is most likely to favor the enol tautomer over the ketone tautomer?

Two structures are shown. The structure numbered 4 shows 2,5-Heptanedione with SMILES string CCC(=O)CCC(=O)C. The structure numbered 5 shows Methyl valerate with SMILES string CCCCC(=O)OC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

16) Which one of the compounds shown is most likely to favor the enol tautomer over the ketone tautomer?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

17) Which of the given statements explains the keto-enol equilibrium shown below?

$A partially reversible reaction that’s forward favored shows 3,5-Heptanedione with SMILES string CCC(=O)CC(=O)CC form (4Z)-5-Hydroxy-4-hepten-3-one with SMILES string O=C(/C=C(\O)CC)CC.$

A) simple enols are more stable

B) the enol tautomer is stabilized by the conjugated π system

C) the enol tautomer is stabilized by the intramolecular hydrogen bonding

D) the diketone is less coplanar

E) both B and C

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

18) Explain why the equilibrium shown favors the enol tautomer.

A partially reversible reaction that’s forward favored shows 2,4-Pentanedione with SMILES string CC(=O)CC(=O)C form (3Z)-4-Hydroxy-3-penten-2-one with SMILES string C/C(=C/C(=O)C)/O.

A) The enol tautomer is stabilized by the intramolecular hydrogen bonding between the OH and the carbonyl group.

B) The enol tautomer is stabilized by the conjugated π system.

C) The enol tautomer is stabilized by lacking a conjugated π system.

D) A and B

E) A and C

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

19) Explain why the equilibrium shown favors the enol tautomer.

A partially reversible reaction that’s forward favored shows 2,4-Cyclohexadien-1-one with SMILES string C1C=CC=CC1=O form phenol with SMILES string c1ccc(cc1)O.

A) The enol tautomer is stabilized by the intramolecular hydrogen bonding.

B) The enol tautomer is stabilized by the conjugated π system of the aromatic system.

C) The enol tautomer is stabilized by lacking a conjugated π system.

D) A and B

E) A and C

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

20) What is the structure of the enol produced when 3,3,6-trimethyl-4-heptanone is treated with acid?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

21) Provide the structure of the enolate when acetophenone is treated with a strong base.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

22) Which of the bases shown will completely convert 1,4-cyclohexanedione into an enolate?

A) sodium hydroxide

B) sodium ethoxide

C) LDA

D) sodium hydride

E) both C and D

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

23) Which of the compounds shown represents an enolate?

Four structures are shown. The first structure has SMILES string C=C/[O+]=C/C(C)[O-]. The second structure has SMILES string C=COC(=O)CC. The third structure has SMILES string C=CO/C([O-])=C/C. The fourth structure has SMILES string CCC(=O)O[CH-]C.

A) I

B) II

C) III

D) IV

E) both B and C

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

24) Which one of the compounds shown would undergo racemization at the α-stereocenter in the presence of a base?

Four structures are shown. The first structure has SMILES string C[C@]12CCCCC1CCCC2=O. The second structure has SMILES string [H][C@@]12CCCCC1CCCC2=O. The third structure has SMILES string C[C@]12CCCC[C@]1(C)C(=O)CCC2. The fourth structure has SMILES string C[C@@]12CCCCC1CCCC2=O.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

25) What are the resonance structures of the enolate formed when the given ketone is treated with a base?

A) I and II

B) I and IV

C) II and III

D) I and III

E) II and V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

26) What are the resonance structures of the enolate formed when the given ketone is treated with a base?

A) I and II

B) I and IV

C) II and III

D) I and III

E) II and V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

27) What are the resonance structures of the enolate formed when the given ester is treated with a base?

A structure shows 3-Methyltetrahydro-2H-pyran-2-one with SMILES string CC1CCCOC1=O.

A) I and II

B) I and IV

C) II and III

D) I and III

E) II and V

Diff: 2

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

28) Which of the compounds shown would not undergo racemization in the presence of a base?

Four structures are shown. The first structure has SMILES string [H][C@]1(C(C)=O)CCCCC1. The second structure has SMILES string [H][C@]1(C(C)=O)CCCC(C)(C)C1. The third structure has SMILES string [H][C@]1(C(C)=O)CCC(C)(C)CC1. The fourth structure has SMILES string CC(=O)[C@@]1(C)CCCCC1.

A) I

B) II

C) III

D) IV

E) II and III

Diff: 3

Learning Objective: 21.1 Write a mechanism for the acid- or base-catalyzed tautomerization of an aldehyde or ketone, and describe the conditions required for the formation of an enolate

29) What is the predicted major product of the reaction shown?

A partial reaction shows 2,2,6-Trimethylcyclohexanone with SMILES string CC1CCCC(C1=O)(C)C.

Three structures are shown. The first structure shows 2-Chloro-2,6,6-trimethylcyclohexanone with SMILES string CC1(CCCC(C1=O)(C)Cl)C. The second structure has SMILES string CC1(C)CCCC(CCl)C1=O. The third structure shows 2-(Chloromethyl)-2,6-dimethylcyclohexanone with SMILES string CC1CCCC(C1=O)(C)CCl.

Two structures are shown. The structure numbered 4 has SMILES string CC1(Cl)CCCC(C)(Cl)C1=O. The structure numbered 5 has SMILES string CC1(CCl)CCCC(CCl)C1=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

30) What is the predicted major product of the reaction shown?

A partial reaction shows 2,2,6,6-Tetramethylcyclohexanone with SMILES string CC1(CCCC(C1=O)(C)C)C react with hydronium and chlorine molecule.

Four structures are shown. The first structure shows 2-Chloro-2,6,6-trimethylcyclohexanone with SMILES string CC1(CCCC(C1=O)(C)Cl)C. The second structure has SMILES string CC1(C)CCCC(C)(CCl)C1=O. The third structure has SMILES string CC1(C)CCC(Cl)C(C)(C)C1=O. The fourth structure has SMILES string CC1(C)CC(Cl)CC(C)(C)C1=O.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

31) What is the predicted major product of the reaction shown?

A partial reaction shows 2-Methylcyclohexanone with SMILES string CC1CCCCC1=O react with hydronium and chlorine molecule.

Four structures are shown. The first structure shows 2-Chloro-6-methylcyclohexanone with SMILES string CC1CCCC(Cl)C1=O. The second structure shows 2-Chloro-2-methylcyclohexanone with SMILES string CC1(CCCCC1=O)Cl. The third structure has SMILES string O=C1CCCCC1CCl. The fourth structure has SMILES string CC1CC(Cl)CCC1=O.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

32) What are the predicted products of the reaction shown?

A partial reaction shows 3-Phenyl-1-propanol with SMILES string c1ccc(cc1)CCCO react first with PCC and dicholoromethane and then with hydronium and bromine molecule.

Three structures are shown. The first structure shows 3-Phenylpropanal with SMILES string c1ccc(cc1)CCC=O. The second structure has SMILES string OC(Br)CCc1ccccc1. The third structure shows 2-Bromo-3-phenylpropanal with SMILES string BrC(C=O)Cc1ccccc1 .

Two structures are shown. The structure numbered 4 shows 3-(4-Bromophenyl)propanal with SMILES string Brc1ccc(cc1)CCC=O. The structure numbered 5 shows 3-Phenylpropanoyl bromide with SMILES string c1ccc(cc1)CCC(=O)Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

33) What reagents are needed to carry out the conversion shown?

$A reaction shows 2-Methyl-1-pentanol with SMILES string CCCC(C)CO form (2 E)-2-Methyl-2-pentenal with SMILES string CC/C=C(\C)/C=O.$

A) 1. PCC/CH2Cl2; 2. H3O+/Br2; 3. NaCN

B) 1. PCC/CH2Cl2; 2. H2O/HBr; 3. NaOCH3

C) 1. NaOEt; 2. H3O+

D) 1. PCC/CH2Cl2; 2. H3O+/Br2; NaOCH2CH3

E) 1. NaOH; 2. heat

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

34) What reagents are needed to carry out the conversion shown?

A reaction shows Phenol with SMILES string c1ccc(cc1)O form 2-Oxocyclohexanecarbonitrile with SMILES string C1CCC(=O)C(C1)C#N.

A) 1. PCC/CH2Cl2; 2. H3O+/Br2; 3. NaCN

B) 1. PCC/CH2Cl2; 2. NaCN; 3. H3O+

C) 1. NaOEt; 2. H3O+

D) 1. PCC/CH2Cl2; 2. H3O+/CN; NaOCH2CH3

E) 1. NaOH; 2. NaCN; 3. heat

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

35) What is the predicted major product of the reaction shown?

A partial reaction shows 2,3-Dimethyl-1-phenyl-1-pentanone with SMILES string CCC(C)C(C)C(=O)c1ccccc1 react first with hydronium and bromine molecule and then with pyridine.

$Two structures are shown with a plus symbol between them. The first structure has SMILES string CC/C(C)=C(C)/C(=O)c1ccccc1. The second structure has SMILES stringCC/C(C)=C(C)\C(=O)c1ccccc1. A number below the two structures reads 1.$

A structure numbered 2 with SMILES string CCC(C)C(C)(Br)C(=O)c1ccccc1 is shown.

$Two structures are shown with a plus symbol between them. The first structure has SMILES string CCC(C)/C(C)=C(O)/c1ccccc1. The second structure has SMILES string CC/C(C)=C(C)\C(=O)c1ccccc1. A number below the two structures reads 3.$

A structure numbered 4 with SMILES string C=C(C(=O)c1ccccc1)C(C)CC is shown.

$Two structures are shown with a plus symbol between them. The first structure has SMILES string CCC(C)/C(C)=C(O)/c1ccccc1. The second structure has SMILES string CCC(C)/C(=C(O)\c1ccccc1)C(C)C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

36) What is the predicted major product of the reaction shown?

A partial reaction shows 2-Methyl-1-phenyl-1-propanone with SMILES string CC(C)C(=O)c1ccccc1 react with hydronium and bromine molecule.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

37) What is the predicted major product of the reaction shown?

Two structures are shown. The structure numbered 4 shows 2-Bromo-3-methylbutanoyl bromide with SMILES string CC(C)C(C(=O)Br)Br. The structure numbered 5 has SMILES string CC(C)CC(O)(O)Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

38) What is the predicted major product of the reaction shown?

Four structures are shown. The first structure has SMILES string CCC(C)(C)C(=O)Br. The second structure has SMILES string CCC(C)(Br)C(=O)O. The third structure has SMILES string CC(Br)C(C)(C)C(=O)O. The fourth structure has SMILES string CCC(C)(Br)C(=O)Br.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

39) What is the predicted major product of the reaction shown?

Two structures are shown. The structure numbered 4 has SMILES string O=C(Br)C1(Br)CCCCC1. The structure numbered 5 has Cyclohexanecarbonyl bromide with SMILES string BrC(=O)C1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

40) What reagents are needed to carry out the conversion shown?

A) 1. H3O+/heat; 2. Br2PBr3; 3. H2O

B) 1. Br2PBr3; 2. H2O

C) 1. HBr; 2. H2SO4; 3. H3O+

D) 1. NaOH/Br2; 2. H3O+

E) 1. NaOH/heat; 2. HBr

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

41) What is the name of the reaction in which a carboxylic acid can undergo alpha halogenation?

A) Haloform reaction

B) Hell-Volhard-Zelinsky reaction

C) Claisen reaction

D) Williamson synthesis

E) Stork reaction

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

42) Which of the given ketones will give a positive haloform test?

A) 3-heptanone

B) 3-hexanone

C) cyclohexanone

D) 2-pentanone

E) 2-methyl-3-hexanone

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

43) Which of the given ketones will give a positive haloform test?

A) 3-heptanone

B) 4-decanone

C) acetone

D) 3-pentanone

E) 3-hexanone

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

44) What is the organic by-product in a haloform reaction?

A) an ether

B) a haloform

C) an alcohol

D) an ester

E) an amide

Diff: 1

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

45) What is the predicted major product of the reaction shown?

Three structures are shown. The first structure shows 2-Bromo-1-(1-methylcyclohexyl)ethenone with SMILES string CC1(CCCCC1)C(=O)CBr. The second structure has SMILES string CC1(C(=O)C(Br)(Br)Br)CCCCC1. The third structure has SMILES string CC(O)(O)C(=O)C1(C)CCCCC1.

Two structures are shown. The structure numbered 4 has SMILES string CC(O)(OBr)C1(C)CCCCC1. The structure numbered 5 has SMILES string has SMILES string CC1(C(=O)O)CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

46) Provide the reagents necessary to convert acetophenone to benzoic acid.

A) PCC/CH2Cl2

B) 1. NaOH/Br2

2. H3O+

C) 1. KMnO4/NaOH/H2O

2. H3O+

D) 1. Br2/PBr3

2. H2O

E) both B and C

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

47) What is the predicted major product of the reaction shown?

An incomplete reaction shows 3,3-Dimethyl-2-hexanone with SMILES string CCCC(C)(C)C(=O)C react first with sodium hydroxide and iodine molecule and second with hydronium.

Three structures are shown. The first structure has SMILES string CCCC(C)(C)C(=O)CI. The second structure has SMILES string CCCC(C)(C)C(=O)O. The third structure has SMILES string CCCC(C)(C)C(=O)C(I)(I)I.

Two structures are shown. The structure numbered 4 has SMILES string CCCC(C)(C)C(=O)I. The structure numbered 5 has SMILES string CCCC(C)(C)C(O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

48) What is the predicted major product of the reaction sequence shown?

Five structures are shown. The first and second structures show Methyl 3-cyclohexyl-2,2-dimethylpropanoate with SMILES string CC(C)(CC1CCCCC1)C(=O)OC. The third structure has SMILES string CCC(=O)C(C)(C)CC1CCCCC1. The fourth structure has SMILES string CC(C)(CC1CCCCC1)C(=O)I. The fifth structure has SMILES string COC(O)C(C)(C)CC1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

49) What reagents are necessary to carry out the conversion shown?

A reaction shows 1-Cyclohexylethanone with SMILES string CC(=O)C1CCCCC1 form a product with SMILES string CNC(=O)C1(Br)CCCCC1.

A) 1. NaOH/Br2; 2. H3O+; 3. CH3NH2

B) 1. NaOH; 2. H3O+; 3. Br2/PBr3; 4. NH3

C) 1. NaOH/I2; 2. H3O+; 3. Br2/PBr3; 4. CH3NH2

D) 1. NaOH/I2; 2. H3O+; 3. HBr; 4; H3O+; 5. CH3NH2

E) 1. NaOH/Br2; 2. H3O+; 3. NaOH/H2O; 4.NH3

Diff: 3

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

50) Which reactant would yield m-chlorobenzoic acid using the haloform reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.2 Predict the products of alpha halogenation of enols and enolates, including the Hell-Volhard-Zelinsky reaction and the haloform reaction

51) Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?

A) butanal

B) 2-methylbutanal

C) 3-methylpentanal

D) 2,2-dimethylbutanal

E) pentanal

Diff: 1

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

52) In an aldol mechanism, the ________ attacks the aldehyde.

A) carbonyl carbon

B) hydroxide ion

C) alkoxide ion

D) enolate

E) proton

Diff: 1

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

53) What is the predicted major product of the reaction shown?

An incomplete reaction shows Butyraldehyde with SMILES string CCCC=O react with sodium hydroxide and water.

Three structures are shown. The first structure shows 2-Ethyl-3-oxohexanal with SMILES string CCCC(=O)C(CC)C=O. The second structure shows 2-Ethyl-3-hydroxyhexanal with SMILES string CCCC(C(CC)C=O)O. The third structure shows 2-Ethyl-1,3-hexanediol with SMILES string CCCC(C(CC)CO)O.

Two structures are shown. The structure numbered 4 has SMILES string CCCC(C=O)C(=O)CC. The structure numbered 5 has SMILES string CCCC(=O)C(CC)CO.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

54) What is the predicted major product of the reaction shown?

An incomplete reaction shows butanal react with 2,2-dimethylpentanal react with sodium hydroxide and water.

Three structures are shown. The first structure has SMILES string CCCC(C)(C)C(O)C(C=O)CC. The second structure has SMILES string CCCC(O)C(C=O)C(C)(C)CCC. The third structure has SMILES string CCCC(O)C(C=O)CC.

Two structures are shown. The structure numbered 4 has SMILES string CCCC(C)(C)C(=O)C(O)C(C)(C)CCC. The structure numbered 5 has SMILES string CCCC(O)C(C)(C)CCC.

A) I

B) II and IV

C) III

D) I and III

E) V

Diff: 2

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

55) What is the predicted major product of the reaction shown?

An incomplete reaction shows Butyraldehyde with SMILES string CCCC=O react first with LDA, second with 1-Methylcyclohexanecarbaldehyde, and third with a water molecule.

$Three structures are shown. The first structure has SMILES string CCC(C=O)C(=O)C1(C)CCCCC1. The second structure has SMILES string CCC(CO)C(O)C1(C)CCCCC1. The third structure has SMILES string C/C=C(C=O)\C(=O)C1(C)CCCCC1.$

Two structures are shown. The structure numbered 4 has SMILES string CCC(C=O)C(O)C1(C)CCCCC1. The structure numbered 5 has SMILES string CCC(CO)C(=O)C1(C)CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

56) What is the predicted product when cyclohexanone reacts with aqueous sodium hydroxide at 100°C?

Three structures are shown. The first structure has SMILES string O=C1CCCC=C1C2CCCCC2. The second structure has SMILES string O=C1CCCC=C1C2CCCCC2=O. The third structure has SMILES string O=C1CCCCC1C2=CCCCC2.

$Two structures are shown. The structure numbered 4 has SMILES string O=C/1CCCCC1=C/2CCCCC2. The structure numbered 5 has SMILES string O=C2CCC/C(=C\1CCCCC1)C2.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

57) What is the predicted product of the reaction shown?

An incomplete reaction shows 3-Methylpentanal with SMILES string CCC(C)CC=O react with sodium hydroxide and water in the presence of heat.

$Two structures are shown. The first structure has SMILES string CCC(C)C/C=C(C=O)\C(C)CC. The second structure has SMILES string CCC(C)/C=C/C(C=O)C(C)CC.$

Two structures are shown. The structure numbered 3 has SMILES string CCC(C)CC(=O)C(C=O)C(C)CC. The structure numbered 4 has SMILES string C=C(C(=O)CC(C)CC)C(C)CC.

A structure numbered 5 with SMILES string CCC(C)CCC(C=O)C(C)CC is shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

58) What is the predicted product of the reaction shown?

An incomplete reaction shows Piperonal with SMILES string c1cc2c(cc1C=O)OCO2 and Benzaldehyde with SMILES string C1=CC=C(C=C1)C=O react with sodium hydroxide and water in the presence of heat.

Two structures are shown. The first structure has SMILES string O=C(/C=C/c2ccc1OCOc1c2)c3ccccc3. The second structure has SMILES string O=C(/C=C/c1ccccc1)c3ccc2OCOc2c3.

Two structures are shown. The structure numbered 3 has SMILES string O=C(CC(=O)c2ccc1OCOc1c2)c3ccccc3. The structure numbered 4 has SMILES string C=C(CC(=O)c2ccc1OCOc1c2)c3ccccc3.

A) I

B) II

C) III

D) IV

E) no reaction

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

59) Which one of the following is not a possible product when a crossed aldol addition reaction is carried out with ethanal and butanal as reactants?

Three structures are shown. The first structure has SMILES string CCCC(O)C(C=O)CC. The second structure has SMILES string CCCC(O)C(CC)CC=O. The third structure has SMILES string CCC(C=O)C(C)O.

Two structures are shown. The structure numbered 4 has SMILES string CCCC(O)CC=O. The structure numbered 5 has SMILES string CC(O)CC=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

60) What is the predicted product of the reaction shown?

An incomplete reaction shows cyclohexanone with SMILES string C1CCC(=O)CC1 and benzaldehyde with SMILES string C1=CC=C(C=C1)C=O react with sodium hydroxide and water in the presence of heat.

Three structures are shown. The first structure has SMILES string O=C1CCCC=C1Cc2ccccc2. The second structure has SMILES string O=C/1CCCCC1=C/c2ccccc2. The third structure has SMILES string O=C1CCCC=C1Cc2ccccc2.

Two structures are shown. The structure numbered 4 has SMILES string O=C1CCCCC1Cc2ccccc2. The structure numbered 5 has SMILES string O=C(C1=CCCCC1)c2ccccc2.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

61) What is the predicted product of the reaction shown?

An incomplete reaction shows 2-Furaldehyde with SMILES string c1cc(oc1)C=O and 3-Methylbutanal with SMILES string CC(C)CC=O react with sodium hydroxide and water in the presence of heat.

Three structures are shown. The first structure has SMILES string CC(C)C(C=O)C(=O)c1ccco1. The second structure has SMILES string CC(C)C(CO)C(=O)c1ccco1. The third structure has SMILES string C/C(C)=C(C=O)/C(=O)c1ccco1.

$Two structures are shown. The structure numbered 4 has SMILES string CC(C)/C(C=O)=C\c1ccco1. The structure numbered 5 has SMILES string CC(C)(C=O)C(O)c1ccco1.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

62) What is the predicted product of the reaction shown?

$Two structures are shown. The structure numbered 4 has SMILES string CC(C)/C(C=O)=C\c1ccco1. The structure numbered 5 has SMILES string CC(C)(C=O)C(O)c1ccco1.$

$Five structures are shown. The first structure has SMILES string CC(C)/C(C=O)=C\C1=CC=CC1. The second structure has SMILES string CC(C)/C(=C\C1=CC=CC1)C(=O)O. The third structure has SMILES string CC(C)C(CO)CC1=CC=CC1. The fourth structure has SMILES string CC(CCC=O)C(=O)C1=CC=CC1. The fifth structure has SMILES string C/C(CCC=O)=C(O)\C1=CC=CC1.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

63) What is the predicted product of the reaction shown?

An incomplete reaction shows 1,3-Cyclopentadiene-1-carbaldehyde with SMILES string C1C=CC=C1C=O and 3-Methylbutanal with SMILES string CC(C)CC=O react with sodium hydroxide and water in the presence of heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

64) What reactants would give the aldol condensation product shown?

Two structures are shown with a plus symbol between them. The first structure shows benzaldehyde with SMILES string C1=CC=C(C=C1)C=O. The second structure shows Phenylacetaldehyde with SMILES string c1ccc(cc1)CC=O. Number below reads 1.

Two structures are shown with a plus symbol between them. The first structure shows Acetophenone with SMILES string CC(=O)c1ccccc1. The second structure shows 1-Phenyl-1-propanone with SMILES string CCC(=O)c1ccccc1. Number below reads 2.

Two structures are shown with a plus symbol between them. The first structure shows Acetophenone with SMILES string CC(=O)c1ccccc1. The second structure shows benzaldehyde with SMILES string C1=CC=C(C=C1)C=O. Number below reads 3.

Two structures are shown with a plus symbol between them. The first structure shows Phenylacetaldehyde with SMILES string c1ccc(cc1)CC=O. The second structure shows Acetophenone with SMILES string CC(=O)c1ccccc1. Number below reads 4.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

65) What reactants would give the aldol condensation product shown?

$A structure shows (2 E)-2,3-Diphenylacrylaldehyde with SMILES string c1ccc(cc1)/C=C(/C=O)\c2ccccc2.$

Two structures are shown with a plus symbol between them. The first structure shows Acetophenone with SMILES string CC(=O)c1ccccc1. The second structure shows Benzaldehyde with SMILES string C1=CC=C(C=C1)C=O. Number below reads 3.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

66) What reactants would give the aldol condensation product shown?

$A structure shows (2 E)-3-(2-Furyl)-2-methylacrylaldehyde with SMILES string C/C(=C\c1ccco1)/C=O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

67) What reactant would give the aldol condensation product shown?

A structure shows 2-Cyclohexen-1-one with SMILES string C1CC=CC(=O)C1.

Three structures are shown. The first structure has SMILES string CC(=O)CCCC=O. The second structure has SMILES string CC(=O)CCCCC=O. The third structure has SMILES string CC(=O)CCCC(C)=O.

Two structures are shown. The structure numbered 4 has SMILES string COC(=O)CCCCC=O. The structure numbered 5 has SMILES string COC(=O)CCCCC(C)=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

68) What is the predicted product of the reaction shown?

An incomplete reaction shows 1-Phenyl-1,5-hexanedione with SMILES string CC(=O)CCCC(=O)c1ccccc1 react with sodium hydroxide and water in the presence of heat.

Three structures are shown. The first structure has SMILES string O=C2C=CC(c1ccccc1)CC2. The second structure has SMILES string O=C1C=CCCC1c2ccccc2. The third structure has SMILES string O=C2C=C(c1ccccc1)CCC2.

Two structures are shown. The structure numbered 4 has SMILES string O=C2C=CCC(c1ccccc1)C2. The structure numbered 5 has SMILES string O=C1CCCC=C1c2ccccc2.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

69) What reactants would give the aldol condensation product shown?

A structure shows 1-Cyclopentene-1-carbaldehyde with SMILES string C1CC=C(C1)C=O.

Three structures are shown. The first structure has SMILES string O=CCCCCC=O. The second structure has SMILES string O=CCCCC=O. The third structure has SMILES string CC(CCC=O)O.

A set of two structures numbered 4 and a structure numbered 5 are shown. The first structure of the set of two structures has SMILES string O=C1CCCC1. The second structure has SMILES string C=O. The structure numbered 5 has SMILES string CC(=O)CCCC=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

70) What reactant would give the possible aldol condensation product shown?

A structure shows 1-(1-Cyclohexen-1-yl)ethenone with SMILES string CC(=O)C1=CCCCC1.

Two structures are shown. The first structure has SMILES string CC(=O)CCCCCC=O. The second structure has SMILES string CC(=O)CCCCC=O.

Two structures and a set with two structures are shown. The structure numbered 3 has SMILES string CC(=O)CCCC(C)O. The structure numbered 4 has SMILES string CC(=O)CCCC(C)=O. The set numbered 5 has two structures. The first structure has SMILES string O=C1CCCCC1. The second structure has SMILES string CC(C)=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

71) What reactant(s) would give the possible aldol condensation product shown?

A structure shows (2E)-3-(3,4-Dimethylphenyl)-1-phenyl-2-propen-1-one with SMILES string Cc1ccc(cc1C)/C=C/C(=O)c2ccccc2.

Five structures are shown. The first structure has SMILES string Cc1ccc(C=O)cc1I. The second structure has SMILES string CC(=O)c1ccc(C)c(C)c1. The third structure has SMILES string O=Cc1ccccc1. The fourth structure has SMILES string CC(=O)c1ccccc1. The fifth structure has SMILES string CCC(=O)c1ccccc1.

A) I and II

B) I and III

C) II and III

D) I and IV

E) II and V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

72) What reactant would give the possible aldol condensation product shown?

A structure shows 3-Phenyl-2-cyclohexen-1-one with SMILES string c1ccc(cc1)C2=CC(=O)CCC2.

Five structures are shown. The first structure has SMILES string CC(=O)CCCC(=O)c1ccccc1. The second structure has SMILES string CC(=O)CCC(=O)c1ccccc1. The third structure has SMILES string CCCC(=O)CC(=O)c1ccccc1. The fourth structure has SMILES string CC(=O)C/C=C/C(=O)c1ccccc1. The fifth structure has SMILES string CC(=O)CCCCC(=O)c1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.3 Predict the products and draw a mechanism for an aldol addition or aldol condensation

73) Which of the choices is a major product in a Claisen condensation?

A) α-keto ester

B) β-keto ester

C) β-hydroxy ester

D) γ-hydroxyester

E) β-diketone

Diff: 1

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

74) Which of the choices is a reactive starting material in the Claisen condensation?

A) 3-pentanone

B) butanal

C) ethyl butanoate

D) 1-propanol

E) propanoic anhydride

Diff: 1

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

75) Why shouldn't CH3ONa be used for Claisen condensation of ethylbutanoate?

A) The reaction will proceed too quickly.

B) Using CH3ONa will yield a transesterification product.

C) There will be no reaction.

D) The starting ester will undergo hydrolysis.

E) Ammonium chloride would be required for the reaction to take place.

Diff: 1

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

76) What is the major predicted product of the reaction shown?

An incomplete reaction shows Ethyl propionate with SMILES string CCC(=O)OCC react first with sodium ethoxide and second with hydronium.

Three structures are shown. The first structure has SMILES string CCOC(=O)C(C)C(=O)CC. The second structure has SMILES string CCOC(=O)C(C)C(O)CC. The third structure has SMILES string CCC(=O)C(C)C(=O)CC.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(=O)CCC(=O)CC. The structure numbered 5 has SMILES string CCOC(=O)CC(=O)CC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

77) What is the major predicted product of the reaction shown?

An incomplete reaction shows Ethyl 3-phenylpropanoate react first with sodium ethoxide and second with hydronium.

Five structures are shown. The first structure has SMILES string CC(=O)C(Cc1ccccc1)C(=O)CCc2ccccc2. The second structure has SMILES string CCOC(=O)C(Cc1ccccc1)C(=O)CCc2ccccc2. The third structure has SMILES string CCOC(=O)C(C)C(=O)CCc1ccccc1. The fourth structure has SMILES string CC(=O)C(C)C(=O)CCc1ccccc1. The fifth structure has SMILES string CCOC(C(=O)CCc1ccccc1)C(=O)CCc2ccccc2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

78) What is the major predicted product of the reaction shown?

An incomplete reaction shows ethyl benzoate and ethyl butanoate react first with sodium ethoxide and second with hydronium.

Two structures are shown. The first structure has SMILES string CCOC(=O)CCC(=O)c1ccccc1. The second structure has SMILES string CCCC(=O)OC(=O)c1ccccc1.

Two structures are shown. The structure numbered 3 has SMILES string CCOC(=O)C(CC)C(O)c1ccccc1. The structure numbered 4 has SMILES string CCOC(=O)C(CC)C(=O)c1ccccc1.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

79) What is the structure of reactant (X) in the following reaction?

A reaction shows Methyl phenylacetate with SMILES string COC(=O)Cc1ccccc1 and Compound X react first with sodium methoxide and second with hydronium to form Dimethyl phenylmalonate with SMILES string COC(=O)C(c1ccccc1)C(=O)OC.

Three structures are shown. The first structure has SMILES string COC(=O)OC. The second structure has SMILES string COC=O. The third structure has SMILES string COC(C)=O.

Two structures are shown. The structure numbered 4 has SMILES string COC(=O)CBr. The structure numbered 5 has SMILES string COC(=O)C(=O)OC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

80) What is(are) the predicted product(s) of the reaction shown?

An incomplete reaction shows methyl acetate and methyl propanoate react first with sodium methoxide and second with hydronium.

Two structures are shown. The first structure has SMILES string COC(=O)CC(C)=O. The second structure has SMILES string COC(=O)C(C)C(C)=O.

Two structures are shown. The structure numbered 3 has SMILES string CCC(=O)C(C)C(=O)OC. The structure numbered 4 has SMILES string CCC(=O)CC(=O)OC.

A) I

B) II

C) III

D) IV

E) all of these

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

81) What reactants will yield the given compound as a crossed Claisen condensation product?

A structure shows Ethyl 3-oxobutanoate with SMILES string CCOC(=O)CC(=O)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

82) What is the predicted product of the reaction shown?

An incomplete reaction shows Methyl phenylacetate with SMILES string COC(=O)Cc1ccccc1 and Dimethyl carbonate with SMILES string COC(=O)OC react first with sodium methoxide and second with hydronium.

Four structures are shown. The first structure has SMILES string COC(=O)C(C(=O)OC)c1ccccc1. The second structure has SMILES string COC(=O)CC(=O)c1ccccc1. The third structure has SMILES string COC(=O)C(=O)c1ccccc1. The fourth structure has SMILES string COC(=O)Cc1ccc(C(=O)OC)cc1.

A) I

B) II

C) III

D) IV

E) All of these

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

83) What reactant(s) will yield the given Claisen condensation product?

A structure shows Methyl 3-oxo-2,4-diphenylbutanoate with SMILES string O=C(OC)C(C(=O)Cc1ccccc1)c2ccccc2.

Five structures are shown. The first structure has SMILES string O=C(O)Cc1ccccc1. The second structure has SMILES string COC(=O)Cc1ccccc1. The third structure has SMILES string CCC(=O)Cc1ccccc1. The fourth structure has SMILES string COCC(=O)c1ccccc1. The fifth structure has SMILES string O=C(CO)c1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

84) An intermolecular Claisen condensation is called a(n) ________.

A) Crossed Claisen condensation

B) Direct Claisen condensation

C) Dieckmann cyclization

D) Cyclic Claisen condensation

E) Asymmetrical Claisen condensation

Diff: 1

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

85) Which cannot be used in a Claisen condensation?

A) two esters, both without alpha hydrogens

B) one ester with an alpha hydrogen and one ester without an alpha hydrogen

C) two esters, both with alpha hydrogens

D) all of these

E) none of these

Diff: 1

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

86) What is the predicted product of the reaction shown?

An incomplete reaction shows Diethyl adipate with SMILES string CCOC(=O)CCCCC(=O)OCC react first with sodium ethoxide and second with hydronium.

Three structures are shown. The first structure has SMILES string CCOC(=O)C1=CCCC1=O. The second structure has SMILES string CCOC(=O)C1CCCC1=O. The third structure has SMILES string CCOC(=O)C1=CCCC1.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(=O)C1=CCCC1O. The structure numbered 5 has SMILES string CCOC(=O)C1=CC(=O)CC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

87) What is the predicted product of the reaction shown?

An incomplete reaction shows diethyl heptanedioate react first with sodium ethoxide and second with hydronium.

Three structures are shown. The first structure has SMILES string CCOC(=O)C1CCCCC1=O. The second structure has SMILES string O=C1CCCCCC1=O. The third structure has SMILES string CCOC(=O)C1=CCCCC1=O.

Two structures are shown. The structure numbered 4 has SMILES string O=C1CCCCCO1. The structure numbered 5 has SMILES string CCOC(=O)C1CCCCC1O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

88) Which of the compounds shown can be prepared using the Dieckmann condensation?

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

89) What is the predicted product of the reaction shown?

An incomplete reaction shows Ethyl 2-[(2E)-3-ethoxy-3-hydroxy-2-propen-1-yl]benzoate with SMILES string CCOC(O)=CCC1C=CC=CC=1C(=O)OCC react first with sodium ethoxide and second with hydronium.

Two structures are shown. The first structure has SMILES string CCOC(=O)C2Cc1ccccc1C2=O. The second structure has SMILES string CCOC(=O)C2C(=O)Cc1ccccc12.

A structure numbered 3 with SMILES string O=C2CCc1ccccc1C(=O)C2 is shown.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(=O)C2CCc1ccccc1C2=O. The structure numbered 5 has SMILES string CCOC(=O)C2=C(O)c1ccccc1CC2.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

90) What is(are) the predicted products of the reaction shown?

An incomplete reaction shows a reactant with SMILES string CCOC(=O)CCCC(C)(C)CC(=O)OCC react first with sodium ethoxide and second with hydronium.

Two structures are shown. The first structure has SMILES string CCOC(=O)C1C(=O)CCCC1(C)C. The second structure has SMILES string CCOC(=O)C1CCCC(C)(C)C1=O.

Two structures are shown. The structure numbered 3 has SMILES string CCOC(=O)C1CCC(C)(C)CC1=O. The structure numbered 4 has SMILES string CCOC(=O)C1CC(C)(C)CCC1=O.

A) I

B) II

C) III

D) I and IV

E) I and III

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

91) Provide a stepwise synthesis for the following compound starting with cycloheptene and using the Dieckmann cyclization.

A structure shows Ethyl 2-oxocyclohexanecarboxylate with SMILES string CCOC(=O)C1CCCCC1=O.

A) 1. O3; 2. DMS; 3. excess Na2Cr2O7/H2SO4/H2O; 4. excess CH3CH2OH/H2SO4; 5. NaOCH2CH3; 6. H3O+

B) 1. H2/Pd; 2. Br2; 3. excess CH3CH2OH/H2SO4; 5. NaOCH2CH3; 6. H3O+

C) 1. O3; 2. excess Na2Cr2O7/H2SO4/H2O; 3. excess CH3CH2OH/H2SO4; 4. NaOCH2CH3; 5. H3O+

D) 1. O3; 2. DMS; 3. excess Na2Cr2O7/H2SO4/H2O; 4. excess CH3OH/H2SO4; 5. NaOCH2CH3; 6. H2O

E) 1. Br2/hv; 2. DMS; 3. NaOH; 4. excess CH3CH2OH/H2SO4; 5. NaOCH2CH3; 6. H3O+

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

92) What is the predicted product for the Dieckmann-like cyclization shown?

An incomplete reaction shows Ethyl 2-acetylcyclohexanecarboxylate with SMILES string CC(=O)C1CCCCC1C(=O)OCC react first with sodium ethoxide and second with hydronium.

Three structures are shown. The first structure has SMILES string CCOC(=O)C2C(=O)CC1CCCCC12. The second structure has SMILES string O=C1CC(=O)C2CCCCC12. The third structure has SMILES string O=C2CC1CCCCC1C(=O)O2.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(=O)C2CCC1CCCCC1C2=O. The structure numbered 5 has SMILES string CCOC(=O)C2CC1CCCCC1C2=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

93) What is the predicted major product of the reaction sequence shown?

An incomplete reaction shows Diethyl adipate with SMILES string CCOC(=O)CCCCC(=O)OCC react first with sodium ethoxide and second with hydronium.

The product formed in the previous reaction reacts with hydronium in the presence of heat and again with sodium borohydride and methanol.

Five structures are shown. The first structure has SMILES string OC1CCCC1. The second structure has SMILES string O=C1CCCC1. The third structure has SMILES string CC(=O)CCCCC(C)=O. The fourth structure has SMILES string OC1=CCCC1. The fifth structure has SMILES string O=CCCCCCC=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 20.4 Identify two methods of producing carboxylic acids

94) What is the predicted product of the reaction shown?

An incomplete reaction shows 2-Methylcyclohexanone with SMILES string CC1CCCCC1=O react first with LDA at negative 78 degree Celsius and second with bromoethane.

Three structures are shown. The first structure has SMILES string CCC1(C)CCCCC1=O. The second structure has SMILES string CCC1CCCC(C)C1=O. The third structure has SMILES string CCC1CCC(C)C(=O)C1.

Two structures are shown. The structure numbered 4 has SMILES string CCC1CCC(=O)C(C)C1. The structure numbered 5 has SMILES string CCC1CCCC(=O)C1C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.5 Predict the products obtained when symmetrical or unsymmetrical ketones are alkylated, and identify the reagents necessary to achieve a malonic ester synthesis or an acetoacetic ester synthesis

95) What is the predicted product of the reaction shown?

A structure shows 2-Methylcyclohexanone with SMILES string CC1CCCCC1=O react first with sodium hydride at 25 degree Celsius and second with bromo ethane.

Three structures are shown. The first structure has SMILES string CCC1(C)CCCCC1=O. The second structure has SMILES string CCC1CCCC(C)C1=O. The third structure has SMILES string CCC1CCC(C)C(=O)C1.

Two structures are shown. The structure numbered 4 has SMILES string CCC1CCC(=O)C(C)C1. The structure numbered 5 has SMILES string CCC1CCCC(=O)C1C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

96) What is the predicted product of the reaction shown?

An incomplete reaction shows 2-methyl-3-pentanone react first with LDA at negative 78 degree Celsius and second with iodoethane.

Three structures are shown. The first structure has SMILES string CCC(C)C(=O)C(C)C. The second structure has SMILES string CCC(=O)C(C)(C)CC. The third structure has SMILES string CCCCC(=O)C(C)C.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(CC)C(C)C. The structure numbered 5 has SMILES string CCC(O)(CC)C(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

97) What is the predicted product of the reaction shown?

An incomplete reaction shows 2-methyl-3-pentanone react first with sodium hydride at 25 degree Celsius and second with iodoethane.

Three structures are shown. The first structure has SMILES string CCC(C)C(=O)C(C)C. The second structure has SMILES string CCC(=O)C(C)(C)CC. The third structure has SMILES string CCCCC(=O)C(C)C.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(CC)C(C)C. The structure numbered 5 has SMILES string CCC(O)(CC)C(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

98) What reagents are needed to carry out the conversion shown?

A reaction shows 3-Methyl-2-hexanone with SMILES string CCCC(C)C(=O)C form 4-Methyl-5-nonanol with SMILES string CCCCC(C(C)CCC)O.

A) 1. LDA; 2. CH3CH2Br; 3. NaBH4/CH3OH

B) 1. LDA; 2. CH3Br; 3. NaBH4/CH3OH

C) 1. LDA; 2. CH3CH2CH2Br; 3. CH3OH

D) 1. LDA; 2. CH3CH2Br; 3. CH3OH

E) 1. LDA; 2. CH3CH2CH2Br; 3. NaBH4/CH3OH

Diff: 3

99) What is the predicted product of the reaction shown?

An incomplete reaction shows 1-[3-Methylcyclohexyl]ethenone with SMILES string CC(=O)C1CCCC(C)C1 react first with LDA at negative 78 degree Celsius and second with bromoethane.

Three structures are shown. The first structure has SMILES string CCCC(=O)C1CCCC(C)C1. The second structure has SMILES string CCC1(C(C)=O)CCCC(C)C1. The third structure has SMILES string CCOC(C)C1CCCC(C)C1.

Two structures are shown. The structure numbered 4 has SMILES string CCC1CCC(C)CC1C(C)=O. The structure numbered 5 has SMILES string CCC1CC(C)CC(C(C)=O)C1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

100) What is the predicted product of the reaction shown?

An incomplete reaction shows 1-[3-Methylcyclohexyl]ethenone with SMILES string CC(=O)C1CCCC(C)C1 react first with sodium hydride at 25 degree Celsius and second with bromoethane.

Two structures are shown. The structure numbered 4 has SMILES string CCC1CCC(C)CC1C(C)=O. The structure numbered 5 has SMILES string CCC1CC(C)CC(C(C)=O)C1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

101) Will the following reaction yield the product shown and why or why not?

A reaction shows Cyclopentanone with SMILES string C1CCC(=O)C1 react first with sodium hydride and second with 2-iodo-2-methylbutane to form 2-(2-Methyl-2-butanyl)cyclopentanone with SMILES string CCC(C)(C)C1CCCC1=O.

A) Yes, the reaction will yield the product shown because an SN2 reaction is favored under these conditions.

B) Yes, the reaction will yield the product shown because an E2 reaction is favored under these conditions.

C) No, because the tertiary alkyl halide is too sterically hindered for an SN2 reaction to occur.

D) No, because iodine is not a good leaving group.

E) No, because no electrophile is present.

Diff: 3

102) What is the predicted product of the reaction shown?

An incomplete reaction shows Diethyl malonate with SMILES string CCOC(=O)CC(=O)OCC react first with sodium ethoxide, second with bromopropane, and third with hydronium.

Three structures are shown. The first structure has SMILES string CCCC(=O)CC(=O)OCC. The second structure has SMILES string CCCC(=O)OCC. The third structure has SMILES string CCCC(=O)O.

Two structures are shown. The structure numbered 4 has SMILES string CCCC(C(=O)O)C(=O)O. The structure numbered 5 has SMILES string CCCC(C(=O)OCC)C(=O)OCC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

103) What is the predicted product of the reaction sequence shown?

An incomplete reaction shows Diethyl malonate with SMILES string CCOC(=O)CC(=O)OCC react first with sodium ethoxide and second with iodoethane. The product reacts further with sodium ethoxide and iodoethane and further with hydronium in the presence of heat.

$Three structures are shown. The first structure has SMILES string CCC(=O)O. The second structure has SMILES string CCOC(=O)CC. The third structure has SMILES string CCOC(=O)C(CC)(CC)C(=O)OCC.$

Two structures are shown. The structure numbered 4 has SMILES string CCC(CC)C(=O)O. The structure numbered 5 has SMILES string CCC(CC)(C(=O)O)C(=O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

104) What is the predicted product of the reaction sequence shown?

Three structures are shown. The first structure has SMILES string CCC(C)C(=O)O. The second structure has SMILES string CCC(CC)(C(=O)O)C(=O)O. The third structure has SMILES string CCC(CC)(C(=O)OC)C(=O)OC.

Two structures are shown. The structure numbered 4 has SMILES string CCC(C)C(=O)OC. The structure numbered 5 has SMILES string CCOC(=O)C(CC)(CC)C(=O)OCC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

105) What is the predicted final product of the reaction sequence shown?

An incomplete reaction shows diethyl malonate react first with sodium ethoxide and second with 1-bromopentane. The product reacts with sodium ethoxide and bromoethane and further with hydronium in the presence of heat.

A) 2-methylheptanoic acid

B) 3-methylhexanoic acid

C) 3-methylpentanoic acid

D) 2-methylpentanoic acid

E) ethyl 2-methylheptanoate

Diff: 3

106) What is the predicted product of the reaction sequence shown?

An incomplete reaction shows diethyl malonate with SMILES string CCOC(=O)CC(=O)OCC react first with sodium ethoxide and (Bromoethyl) cyclohexane. The product reacts with sodium ethoxide first and second with benzyl bromide and further with hydronium in the presence of heat.

Three structures are shown. The first structure has SMILES string O=C(O)C(CCC1CCCCC1)Cc2ccccc2. The second structure has SMILES string O=C(O)C(CCC1CCCCC1)(Cc2ccccc2)C(=O)O. The third structure has SMILES string CCOC(=O)C(CCC1CCCCC1)Cc2ccccc2.

Two structures are shown. The structure numbered 4 has SMILES string CCOC(=O)C(CCC1CCCCC1)(Cc2ccccc2)C(=O)OCC. The structure numbered 5 has SMILES string CCC(C)CCCC(=O)Cc1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

107) Provide the reagents necessary to carry out the following conversion using a malonic ester synthesis.

A) 1. NaOCH2CH3; 2. CH3CH2CH2Br; 3. NaOCH2CH3; 4. A structure shows (Bromomethyl)cyclopentane with SMILES string C1CCC(C1)CBr. ;

5. H3O+, heat

B) 1. LDA; 2. A structure shows (Bromomethyl)cyclopentane with SMILES string C1CCC(C1)CBr. ; 4. H3O+, heat

C) 1. LDA; 2. A structure shows Bromocyclopentane with SMILES string C1CCC(C1)Br. ; 4. H3O+, heat

D) 1. NaOCH2CH3; 2. (CH3)2CHCH2Br; 3. NaOCH2CH3; 4. A structure shows (Bromomethyl)cyclopentane with SMILES string C1CCC(C1)CBr. ;

5. H3O+/heat

E) 1. NaOCH2CH3; 2. (CH3)2CHCH2Br; 3. NaOCH2CH3; 4. A structure shows Bromocyclopentane with SMILES string C1CCC(C1)Br. ;

5. H3O+, heat

Diff: 3

108) What is the predicted final product of the reaction sequence shown?

An incomplete reaction shows diethyl malonate with SMILES string CCOC(=O)CC(=O)OCC react first with sodium ethoxide and second with 1,2-Dibromoethane. The product formed further reacts with sodium ethoxide and with hydronium in the presence of heat.

Two structures are shown. The first structure has SMILES string O=C(O)C1CCC(C(=O)O)CC1. The second structure has SMILES string CCOC(=O)C1CCC(C(=O)OCC)CC1.

Three structures are shown. The structure numbered 3 has SMILES string O=C(O)C1CC1. The structure numbered 4 has SMILES string CCC(C(=O)O)C(=O)O. The structure numbered 5 has SMILES string CCCC(=O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

109) What is the predicted final product of the reaction sequence shown?

An incomplete reaction shows Diethyl malonate with SMILES string CCOC(=O)CC(=O)OCC react first with sodium ethoxide and second with 1,5-Dibromopentane. The product formed reacts further with sodium ethoxide and then with hydronium in the presence of heat.

Three structures are shown. The first structure has SMILES string O=C(O)C1CCCC(C(=O)O)C1. The second structure has SMILES string CCOC(=O)C1CCCCC1C(=O)OCC. The third structure has SMILES string O=C(O)C1CCCCC1.

Two structures are shown. The structure numbered 4 has SMILES string CCCCCCC(C(=O)O)C(=O)O. The structure numbered 5 has SMILES string CCCCCCC(=O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

110) Provide the structures of the intermediates and the final product in the following reaction sequence.

An incomplete reaction shows Diethyl malonate with SMILES string CCOC(=O)CC(=O)OCC react first with sodium ethoxide and second with (Bromomethyl)cyclopentane.

A 2-step reaction shows Compound X react with hydronium in the presence of heat to form Compound Y. The second step shows Compound Y react first with thionyl chloride and second with aluminum chloride to form Compound Z.

Five structures are shown. The first structure has SMILES string CCOC(=O)C(CCc1ccccc1)C(=O)OCC. The second structure has SMILES string COC(=O)C(CCc1ccccc1)C(=O)OC. The third structure has SMILES string O=C(O)CCCc1ccccc1. The fourth structure has SMILES string O=C1CCCc2ccccc12. The fifth structure has SMILES string [O-]c1cccc2ccccc12.

A) X is I, Y is II, and Z is III

B) X is II, Y is I, and Z is III

C) X is I, Y is III, and Z is IV

D) X is II, Y is III, and Z is V

E) X is I, Y is IV, and Z is C

Diff: 3

111) Which of the following ketones cannot be prepared using an acetoacetic ester synthesis?

Four structures are shown. The first structure shows 2-Pentanone with SMILES string CCCC(=O)C. The second structure shows 3-Methyl-2-pentanone with SMILES string CCC(C)C(=O)C. The third structure shows 2-Pentanone with SMILES string CCCC(=O)C. The fourth structure shows 3,3-Dimethyl-2-pentanone with SMILES string CCC(C)(C)C(=O)C.

A) I

B) II

C) III

D) IV

E) A and C

Diff: 2

112) What is the predicted final product of the reaction shown?

An incomplete reaction shows Ethyl 3-oxobutanoate with SMILES string CCOC(=O)CC(=O)C react first with sodium ethoxide and second with iodopropane and then with hydronium in the presence of heat.

Three structures are shown. The first structure has SMILES string CCCC(C(C)=O)C(=O)OCC. The second structure has SMILES string CCCC(C(C)=O)C(=O)O. The third structure has SMILES string C/C=C(CCC)/C(=O)O.

Two structures are shown. The structure numbered 4 has SMILES string CCCCC(C)=O. The structure numbered 5 has SMILES string CCCC(C)(O)CC(=O)OCC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

113) What is the predicted product of the reaction sequence shown?

An incomplete reaction shows Ethyl 3-oxobutanoate with SMILES string CCOC(=O)CC(=O)C react first with sodium ethoxide and second with bromoethyl benzene. The product formed further reacts with hydronium in the presence of heat.

Three structures are shown. The first structure has SMILES string CCOC(=O)C(CCc1ccccc1)C(C)=O. The second structure has SMILES string CC(=O)C(CCc1ccccc1)C(=O)O. The third structure has SMILES string C/C=C(CCc1ccccc1)/C(=O)O.

Two structures are shown. The structure numbered 4 has SMILES string CC(=O)CCCc1ccccc1. The structure numbered 5 has SMILES string CCOC(=O)CC(C)(O)CCc1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

114) What is the predicted product of the reaction sequence shown?

An incomplete reaction shows Ethyl 3-oxobutanoate with SMILES string CCOC(=O)CC(=O)C react first with sodium ethoxide and second with iodoethane. The product then reacts first with sodium ethoxide and second with iodoethane.

Three structures are shown. The first structure has SMILES string CCC1(CC)OCCO1. The second structure has SMILES string CCC(CC)C1OCCO1. The third structure has SMILES string CCC(CC)C1(C)OCCO1.

Two structures are shown. The structure numbered 4 has SMILES string CCC(CC)(C(=O)O)C1(C)OCCO1. The structure numbered 5 has SMILES string CCOC(=O)C(CC)(CC)C1(C)OCCO1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

115) What reagents are needed to carry out the following conversion?

A reaction shows Ethyl 3-oxobutanoate with SMILES string CCOC(=O)CC(=O)C form 1-Phenyl-1,3-pentanedione with SMILES string CCC(=O)CC(=O)c1ccccc1.

Labeled 1: Three forward arrows are shown with regents above them. The regent above the first arrow is sodium hydride. The reagent above the second arrow is ?-Toluyl chloride. The reagent above the third arrow is hydronium in the presence of heat.

Labeled 2: Three forward arrows are shown with regents above them. The regent above the first arrow is sodium ethoxide. The reagent above the second arrow is Phenacyl Bromide. The reagent above the third arrow is hydronium in the presence of heat.

Labeled 3: Three forward arrows are shown with regents above them. The regent above the first arrow is sodium ethoxide. The reagent above the second arrow is bromoethyl benzene. The reagent above the third arrow is hydronium in the presence of heat.

Labeled 4: Three forward arrows are shown with regents above them. The regent above the first arrow is sodium ethoxide. The reagent above the second arrow is bromomethyl benzene. The reagent above the third arrow is hydronium in the presence of heat.

A) I

B) II

C) III

D) IV

E) all of them

Diff: 3

116) What reagents are necessary to prepare the following compound starting with ethyl acetoacetate?

A structure shows 3-(2-Oxopropyl)cyclohexanone with SMILES string CC(=O)CC1CCCC(=O)C1.

A) NaOH; 2. A structure shows 3-Cyclohexen-1-one with SMILES string C1CC(=O)CC=C1. ; 3. H3O+, heat

B) NaOCH3; 2. A structure shows 3-Cyclohexen-1-one with SMILES string C1CC(=O)CC=C1.

C) NaOCH2CH3; 2. A structure shows Cyclohexanone with SMILES string C1CCC(=O)CC1. ; 3. H3O+, heat

D) NaOCH2CH3; 2. A structure shows 3-Cyclohexen-1-one with SMILES string C1CC(=O)CC=C1. ; 3. H3O+, heat

E) NaOCH3; 2. A structure shows Cyclohexanone with SMILES string C1CCC(=O)CC1. ; 3. H3O+, heat

Diff: 3

117) Which of the following nucleophiles will perform conjugate addition in a Michael reaction?

A) I

B) I and II

C) III

D) I and IV

E) II and IV

Diff: 1

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

118) Which one of the choices is the most reactive Michael acceptor?

Three structures are shown. The first structure has SMILES string C/C=C/C(=O)OCC. The second structure has SMILES string C/C=C/C(C)=O. The third structure has SMILES string C/C=C/N(=O)=O.

Two structures are shown. The structure numbered 4 has SMILES string C/C=C/C(N)=O. The structure numbered 5 has SMILES string CC[CH-]C#N.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

119) What is(are) the predicted product(s) of the reaction shown?

An incomplete reaction shows (3 E)-4-Cyclohexyl-3-buten-2-one with SMILES string CC(=O)/C=C/C1CCCCC1 react first with Gilman’s reagent (C H 3 C H 2 C H 2) 2 Cu Li and second with hydronium.

Two structures are shown. The first structure has SMILES string CCCC(CC(C)=O)C1CCCCC1. The second structure has SMILES string CCCCC(C(C)=O)C1CCCCC1.

Two structures are shown. The structure numbered 3 has SMILES string CCCC(CC(C)O)C1CCCCC1. The structure numbered 4 has SMILES string CCCC(C)(O)/C=C/C1CCCCC1.

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 2

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

120) What is(are) the predicted product(s) of the reaction shown?

An incomplete reaction shows (3 E)-4-Cyclohexyl-3-buten-2-one with SMILES string CC(=O)/C=C/C1CCCCC1 react first with propyl magnesium bromide and second with hydronium.

Two structures are shown. The first structure has SMILES string CCCC(CC(C)=O)C1CCCCC1. The second structure has SMILES string CCCCC(C(C)=O)C1CCCCC1.

Two structures are shown. The structure numbered 3 has SMILES string CCCC(CC(C)O)C1CCCCC1. The structure numbered 4 has SMILES string CCCC(C)(O)/C=C/C1CCCCC1.

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 2

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

121) What is the predicted product of the reaction shown?

An incomplete reaction shows 2,4-Hexanedione with SMILES string CCC(=O)CC(=O)C react first with potassium hydroxide, second with cyclohexanone, and third with hydronium.

Three structures are shown. The first structure has SMILES string CCC(=O)C(C(C)=O)C1CCCCC1=O. The second structure has SMILES string CCC(=O)C(C(C)=O)C1CCCC(=O)C1. The third structure has SMILES string CCC(=O)C(C(C)=O)C1(C)C=CCCC1.

Two structures are shown. The structure numbered 4 has SMILES string CCC(=O)CC(=O)CC1CCCCC1=O. The structure numbered 5 has SMILES string CCC(=O)CC(C(C)=O)C1CCC(=O)CC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

122) What is the predicted product of the reaction shown?

An incomplete reaction shows Methyl 3-oxobutanoate with SMILES string CC(=O)CC(=O)OC react first with sodium methoxide, second with bromopropene, and third with hydronium.

Three structures are shown. The first structure has SMILES string C=CCC(=O)CC(C)=O. The second structure has SMILES string CCCC(C)(O)CC(=O)OC. The third structure has SMILES string C=CCC(C(C)=O)C(=O)O.

Two structures are shown. The structure numbered 4 has SMILES string C=CCCC(C)=O. The structure numbered 5 has SMILES string C=CCCC(=O)OC.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

123) What reagents are needed to carry out the conversion shown?

A reaction shows 1,3-Cyclohexanedione with SMILES string C1CC(=O)CC(=O)C1 form 3-(2,6-Dioxocyclohexyl)propanenitrile with SMILES string C1CC(=O)C(C(=O)C1)CCC#N.

A) 1. (CH3)2NH; 2. A structure shows Acrylonitrile with SMILES string C=CC#N. ; 3. H3O+

B) 1. LDA; 2. A structure shows Acrylonitrile with SMILES string C=CC#N. ; 3. H3O+

C) 1. LDA; 2. A structure shows (2 E)-2-Butenenitrile with SMILES string C/C=C/C#N. ; 3. H3O+

D) 1. LDA; 2. A structure shows Propiononitrile with SMILES string CCC#N. ; 3. H3O+

E) 1. LDA; 2. (CH3)2NH; 3. A structure shows Propiononitrile with SMILES string CCC#N. ; 3. H3O+

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

124) What is the predicted product of the reaction shown?

An incomplete reaction shows Methyl 3-oxobutanoate with SMILES string CC(=O)CC(=O)OC react first with sodium methoxide and second with 1-Cyclopentyl-2-propen-1-one with SMILES string C=CC(=O)C1CCCC1.

Three structures are shown. The first structure has SMILES string CC(=O)CCCC(=O)C1CCCC1. The second structure has SMILES string COC(=O)C(CCC(=O)C1CCCC1)C(C)=O. The third structure has SMILES string CC(=O)/C=C/CC(=O)C1CCCC1.

Two structures are shown. The structure numbered 4 has SMILES string CC(=O)C(CCC(=O)C1CCCC1)C(=O)O. The structure numbered 5 has SMILES string CC(=O)C/C=C/C(=O)C1CCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

125) Which of the compounds shown can be prepared using the Michael reaction?

Four structures are shown. The first structure has SMILES string CCOC(=O)CC(=O)OCC. The second structure has SMILES string CCC(C)=O. The third structure has SMILES string CC(=O)CCCC(=O)O. The fourth structure has SMILES string CCOC(=O)C(=O)OCC.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

126) What is the predicted product of the reaction shown?

An incomplete reaction shows Methyl 3-oxobutanoate with SMILES string CC(=O)CC(=O)OC react first with sodium methoxide and second with bromopropene.

The product of the previous reaction reacts first with sodium methoxide and bromoethane and then with hydronium and water, and then with lithium aluminum hydride first and hydronium second.

Three structures are shown. The first structure has SMILES string C=CCC(CC)CO. The second structure has SMILES string C=CCC(CC)C(C)O. The third structure has SMILES string C=CCC(CC)C(O)CCC.

Two structures are shown. The structure numbered 4 has SMILES string C=CCC(CC)(C(=O)O)C(C)O. The structure numbered 5 has SMILES string C=CCC(CC)(CO)C(C)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

127) Which of the amines shown will form an enamine with aldehydes and ketones?

Four structures are shown. The first structure has SMILES string CCCN. The second structure has SMILES string CCNCC. The third structure has SMILES string C1CCNC1. The fourth structure has SMILES string CN1CCCCC1.

A) I

B) II

C) III

D) IV

E) II and III

Diff: 1

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

128) Which of the amines shown will form an enamine with aldehydes and ketones?

Four structures are shown. The first structure has SMILES string C1CCNCC1. The second structure has SMILES string CN1CCCCC1. The third structure has SMILES string C1CCNC1. The fourth structure has SMILES string c1ccncc1.

A) I

B) II

C) III

D) IV

E) I and III

Diff: 1

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

129) Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis.

A) CH3NH/H2SO4; 2. A structure shows Cyclohexenone with SMILES string O=C1C=CCCC1. ; 3. H3O+

B) NaOCH3; 2. A structure shows Cyclohexenone with SMILES string O=C1C=CCCC1. ; 3. H3O+

C) (CH3)2NH/H2SO4; 2. A structure shows cyclohexanone with SMILES string O=C1CCCCC1. ; 3. H3O+

D) (CH3)2NH/H2SO4; 2. A structure shows Cyclohexenone with SMILES string O=C1C=CCCC1. ; 3. H3O+

E) CH3NH/H2SO4; 2. A structure shows cyclohexanone with SMILES string O=C1CCCCC1. ; 3. H3O+

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

130) What is the predicted product of the reaction shown?

Three structures are shown. The first structure has SMILES string CC(=O)CCC1CCCCC1N(C)C. The second structure has SMILES string CC(=O)CCC1=C(N(C)C)CCCC1. The third structure has SMILES string C=CC(C)(O)C1CCCCC1=O.

Two structures are shown. The structure numbered 4 has SMILES string CC(=O)CCC1CCCCC1=O. The structure numbered 5 has SMILES string C/C(O)=C/CC1=CCCCC1=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

131) What is the predicted product of the reaction shown?

$Two structures are shown. The first structure has SMILES string CCC(=O)CC(=O)c1ccccc1. The second structure has SMILES string CCC(=O)/C=C(c1ccccc1)\N(C)C.$

A structure numbered 3 has SMILES string O=C(Cl)CCC(=O)c1ccccc1.

Two structures are shown. The structure numbered 4 has SMILES string O=C(O)C/C=C(O)/c1ccccc1. The structure numbered 5 has SMILES string CCC(=O)/C=C/C(O)c1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

132) Provide the reactants necessary to synthesize the following compound using a Stork enamine synthesis.

A structure with SMILES string CCC(=O)CCC(C=O)CC is shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

133) What is the predicted product of the reaction sequence shown?

Five structures are shown. The first structure has SMILES string CC(CCO)C1CCCCC1=O. The second structure has SMILES string CCCCC1CCCCC1=O. The third structure has SMILES string CCCCC1CCCCC1O. The fourth structure has SMILES string CC(CCO)C1CCCCC1O. The fifth structure has SMILES string OCCCC1CCCCC1O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

134) What is the predicted major product of the reaction shown?

An incomplete reaction shows 2-Methyl-1,3-cyclohexanedione with SMILES string CC1C(=O)CCCC1=O and 3-Buten-2-one with SMILES string CC(=O)C=C react with sodium hydroxide in the presence of heat.

Three structures are shown. The first structure has SMILES string CC12C=CC(=O)CC1CCCC2=O. The second structure has SMILES string CC12C(=O)CCC=C1CCCC2=O. The third structure has SMILES string CC12CC(=O)CC=C1CCCC2=O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

135) What is(are) the predicted product(s) of the reaction shown?

An incomplete reaction shows 1-Phenylacetone with SMILES string CC(=O)Cc1ccccc1 and 3-Buten-2-one with SMILES string CC(=O)C=C react with sodium hydroxide in the presence of heat.

Three structures are shown. The first structure has SMILES string O=C2C=Cc1ccccc1C2. The second structure has SMILES string CC1=CC(=O)CCC1c2ccccc2. The third structure has SMILES string O=C2CCC(c1ccccc1)C(O)C2.

Two structures are shown. The structure numbered 4 has SMILES string O=C2C=C(Cc1ccccc1)CCC2. The structure numbered 5 has SMILES string CC2=CC(=O)C(c1ccccc1)CC2.

A) I

B) II and III

C) III and IV

D) IV

E) II and V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

136) What reactants are needed to prepare the given compound using Robinson annulation?

A structure with SMILES string O=C2C=C1CCCC(=O)C1C3CCCCC23 is shown.

Two sets of structures are shown. Each set has two structures with a plus symbol between them. The first set shows 1,3-Cyclohexanedione with SMILES string C1CC(=O)CC(=O)C1 and 1-(1-Cyclohexen-1-yl)ethenone with SMILES string CC(=O)C1=CCCCC1. The second set shows Hexahydro-1,3(2H,4H)-naphthalenedione with SMILES string C1CCC2C(C1)CC(=O)CC2=O and 3-Buten-2-one with SMILES string CC(=O)C=C.

A) I

B) II

C) III

D) IV

E) I and III

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

137) What reactants are needed to prepare the given compound using Robinson annulation?

A structure shows 4a-Methyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone with SMILES string CC12CCCCC1=CC(=O)CC2.

Two sets of structures are shown. Each set has two structures with a plus symbol between them. The first set shows 1-Methyl-2-methylenecyclohexane with SMILES string CC1CCCCC1=C and 3-Buten-2-one with SMILES string CC(=O)C=C. The second set shows 2-Cyclohexen-1-one with SMILES string C1CC=CC(=O)C1 and (3 E)-3-Penten-2-one with SMILES string C/C=C/C(=O)C.

A set numbered 3 shows two structures with a plus symbol between them. The first structure shows 2-Methylcyclohexanone with SMILES string CC1CCCCC1=O. The second structure shows Acrylaldehyde with SMILES string C=CC=O.

Two sets of structures are shown. Each set has two structures with a plus symbol between them. The set numbered 4 shows 2-Methylcyclohexanone with SMILES string CC1CCCCC1=O and (3 E)-3-Penten-2-one with SMILES string C/C=C/C(=O)C. The set shows numbered 5 shows 2-Methylcyclohexanone with SMILES string CC1CCCCC1=O and 3-Buten-2-one with SMILES string CC(=O)C=C.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.6 Predict the products of a conjugate addition reaction, and identify the reagents necessary to achieve a Stork enamine synthesis

138) What are the structures of the intermediates and the final product in the reaction sequence shown?

Five structures are shown. The first structure has SMILES string CCN(CC)C2=Cc1ccccc1CC2. The second structure has SMILES string CC(=O)CCC2C(=O)CCc1ccccc12. The third structure has SMILES string O=C3C=C2CCc1ccccc1C2CC3. The fourth structure has SMILES string CC2C(=O)CCc1ccccc12. The fifth structure has SMILES string O=C3CCC2c1ccccc1CCC2C3.

A) X is I, Y is II, and Z is III

B) X is II, Y is I, and Z is III

C) X is I, Y is III, and Z is IV

D) X is II, Y is III, and Z is V

E) X is I, Y is IV, and Z is C

Diff: 2

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

139) What reagents are needed to carry out the conversion shown?

A reaction shows 1-Cyclohexene-1-carbaldehyde with SMILES string C1CCC(=CC1)C=O form a product with SMILES string CCC1CCCCC1(C)C(=O)OC.

A) 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. Zn(Hg)/HCl

B) 1. (CH3CH2)2CuLi; 2. CH3I; 3. KCr2O7/H2SO4/H2O; 4. CH3OH/H2SO4

C) 1. (CH3CH2)2CuLi; 2. CH3Br; 3. Zn(Hg)/HCl

D) 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. KCr2O7/H2SO4/H2O; 4. CH3OH

E) 1. (CH3CH2)2CuLi; 2. KCr2O7/H2SO4/H2O; 3. NaOH; 4. CH3OH/H2SO4

Diff: 2

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

140) What reagents are needed to carry out the conversion shown?

A reaction shows 1-Cyclohexene-1-carbaldehyde with SMILES string C1CCC(=CC1)C=O form 1,2-Diethyl-1-methylcyclohexane with SMILES string CCC1CCCCC1(C)CC.

A) 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. Zn(Hg)/HCl

B) 1. (CH3CH2)2CuLi; 2. CH3I; 3. KCr2O7/H2SO4/H2O; 4. CH3OH/H2SO4

C) 1. (CH3CH2)2CuLi; 2. CH3Br; 3. Zn(Hg)/HCl

D) 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. KCr2O7/H2SO4/H2O; 4. CH3OH

E) 1. LDA; 2. (CH3CH2O)2C=O; DIBAH

Diff: 2

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

141) Provide the reagents necessary to carry out the following conversion.

A reaction shows cyclohexanone with SMILES string C1CCC(=O)CC1 form 2-Oxocyclohexanecarbaldehyde with SMILES string C1CCC(=O)C(C1)C=O.

A) 1. (CH3CH2)2CuLi; 2. CH3CH2Br; 3. Zn(Hg)/HCl

B) 1. (CH3CH2)2CuLi; 2. CH3I; 3. KCr2O7/H2SO4/H2O; 4. CH3OH/H2SO4

C) 1. LDA; 2. (CH3CH2O)2C=O; Zn(Hg)/HCl

D) 1. LDA; 2. (CH3O)2C=O

E) 1. LDA; 2. (CH3CH2O)2C=O; DIBAH

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

142) What is the structure of the reactant (X) necessary to carry out the conversion shown?

A reaction shows 5-Oxohexanal with SMILES string O=CCCCC(=O)C react with sodium hydroxide in the presence of heat to form an intermediate product that reacts with "X" to form a product with SMILES string CC1C=CC(C)C2C(=O)CCCC12.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

143) What is an appropriate stepwise synthesis for the conversion shown?

A reaction shows Benzaldehyde with SMILES string c1ccc(cc1)C=O form a product with SMILES string CC/C(=C/c1cccc(Cl)c1)C(=O)Cl.

A) 1. Cl2/FeCl3; 2. A structure shows Methyl Butyrate with SMILES string CCCC(=O)OC. /NaOCH3; 3. H3O+; 4. SOCl2

B) 1. HCl/AlCl3; 2. A structure shows Methyl Butyrate with SMILES string CCCC(=O)OC. /NaOCH3; 3. SOCl2; 4. NaOH

C) 1. Cl2/FeCl3; 2. A structure shows Methyl propionate with SMILES string CCC(=O)OC. /NaOCH3; 3. H3O+; 4. SOCl2

D) 1. Cl2/FeCl3; 2. A structure shows 3-Hexanone with SMILES string CCCC(=O)CC. /NaOCH3; 3. H3O+; 4. SOCl2

E) 1. HCl/AlCl3; 2. A structure shows 3-Hexanone with SMILES string CCCC(=O)CC. ; 3. SOCl2; 4. NaOH

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

144) Which one of the reaction sequences shown will yield 2,2-dimethylcyclohexane-1,3-dione?

An incomplete reaction numbered 1 shows 1,3-Cyclohexanedione with SMILES string C1CC(=O)CC(=O)C1 react first with excess methyl magnesium bromide and second with hydronium.

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

145) What reagents are needed to carry out the conversion shown?

A reaction shows a reactant with SMILES string CCOC(=O)CCCCC(C)(C)C(=O)OCC form a product with SMILES string CC1CCCC(C)(C)C1=O.

A) 1. NaOCH2CH3; 2. CH3Br

B) 1. NaOCH2CH3; 2. CH3I; 4. H3O+, heat

C) 1. NaOCH2CH3; 2. NaOCH2CH3; 3. CH3CH2Br; 4. H2SO4

D) 1. NaOCH2CH3; 2. NaOCH2CH3; 3. CH3Br; 4. H3O+, heat

E) 1. NaOCH2CH3; 2. CH3Br; 3. H3O+, heat

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

146) What reagents are necessary to carry out the conversion shown?

A reaction shows Dimethyl 4-oxoheptanedioate with SMILES string COC(=O)CCC(=O)CCC(=O)OC form 1,4-Cyclohexanedione with SMILES string C1CC(=O)CCC1=O.

A) 1. Na2Cr2O7/H2SO4/H2O; 2. H3O+/EtOH; 3. H3O+, heat

B) 1. HOCH2CH2OH; 2. NaOCH2CH3; 3. excess H3O+, heat

C) 1. HOCH2CH2OH, H2SO4; 2. NaOCH3; 3. excess H3O+, heat

D) 1. NaOCH2CH3; 2. NaOCH2CH3; 3. CH3Br; 4. H3O+, heat

E) 1. Na2Cr2O7/H2SO4/H2O; 2. H3O+/EtOH; 3. NaOEt; 4. H3O+, heat

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

147) What is an appropriate stepwise synthesis for the following synthesis that uses 1-propanol as the only source of carbon and any other reagents as needed?

A reaction shows C H 3 C H 2 C H 2 O H form C H 3 C H 2 C H 2 C (C H 3) H C H 2 OH.

A) 1-propanol reacts with PCC/CH2Cl2 to yield an intermediate that reacts with LDA to yield intermediate X, which has a resonance form Y. 1-propanol also reacts with PCl3 to yield an intermediate Z that reacts with intermediate X, which undergoes the following series of reactions to yield the product: 1. Na2Cr2O7/H2SO4/H2O; 2. Excess CH3CH2CH2OH/H2SO4.

B) 1-propanol reacts with PCC/CH2Cl2, then the product reacts with LDA to produce intermediate X, which has resonance forms. 1-propanol reacts with PCl3, then the product reacts with intermediate X to yield intermediate Y. Intermediate Y reacts with NaBH4/CH3OH to yield the product.

C) 1-propanol reacts with PCl3 to yield intermediate X. 1-propanol also undergoes the following reaction sequence: 1. Na2Cr2O7/H2SO4/H2O; 2. excess CH3CH2CH2OH/H2SO4; 3. LDA; 4. Intermediate X. This yields the product.

D) A or B

E) B or C

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

148) What is an appropriate stepwise synthesis for the following synthesis that uses 1-propanol as the only source of carbon and any other reagents as needed?

A reaction shows C H 3 C H 2 C H 2 O H form C H 3 C H 2 C H 3 C (C H 3) H C (double bond O) O C H 2 C H 2 C H 3.

D) A or B

E) A or C

Diff: 3

Learning Objective: 21.7 Identify two methods for preparing difunctionalized compounds

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Chapter 21 Alpha Carbon Chemistry Enols And Enolates

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David R. Klein

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