Test Questions & Answers Chapter 11 Synthesis

Organic Chemistry, 4e (Klein)

Chapter 11 Synthesis

1) Predict the major product(s) for the reaction shown.

A reaction shows the reactant with SMILES string CCC(=C)C(C)C reacts with hydrogen bromide, H B r to form the product (represented with a question mark).

A) I

B) II

C) III

D) IV

E) I, III, and IV

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

2) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CCC(=C)C(C)C reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC(CBr)C(C)C.

A) HBr

B) Br2/hv

C) Br2/ROOR

D) HBr/ROOR

E) hv /NBS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

3) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CC(=C)C(C)(C)C reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of BrC/C(=C)C(C)(C)C.

A) HBr

B) Br2/hv

C) Br2/ROOR

D) HBr/ROOR

E) hv /NBS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

4) Select the best reagents for the reaction shown.

A) HBr

B) Br2/hv

C) Br2, CCl4

D) HBr/ROOR

E) hv /NBS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

5) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CC(C)C(=C)C reacts with a reagent (represented with a question mark), to form the product that has a four-carbon chain, in which C-1 is single-bonded to a bromine atom, C-2 is wedge-bonded to a methyl group, and dash-bonded to a hydroxyl group, O H, and C-3 is bonded to a methyl group.

A) HBr

B) Br2/H2O

C) Br2, CCl4

D) HBr/ROOR

E) hv /NBS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

6) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CC(C)C(C)O reacts with a reagent (represented with a question mark), to form the product that has a SMILES string CC=C(C)C.

A) NaOH

B) heat/H2SO4

C) CH3CO2H

D) NaOEt

E) B and D

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

7) Provide the major product(s) for the following synthesis.

A reaction shows the reactant that has a cyclopentane ring, in which C-1 is single-bonded to a methyl group, C-1 is double-bonded to C-2, C-2 is bonded to a two-carbon chain, which is further single-bonded to a bromine atom, B r reacts with sodium hydrosulfide, N a S H to form the product (represented with a question mark).

A) I

B) II

C) III

D) IV

E) I and III

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

8) Select the best reagents for the reaction shown.

A reaction shows the reactant that has a cyclopentane ring, in which C-2 is bonded to a methyl group, and C-1 is bonded to a bromine atom and a methyl group reacts with a reagent (represented with a question mark), to form the product that has a SMILES string CC1=C(CCC1)C.

A) NaOtBu

B) HBr

C) H2SO4

D) NaOH

E) NaSH

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

9) Select the best reagents for the reaction shown.

A) NaOtBu

B) HBr

C) H2SO4

D) NaOH

E) NaSH

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

10) Provide the major product(s) obtained from the reaction shown.

A reaction shows the reactant with SMILES string CC1CCC1CCl reacts with D B U to form the product (represented with a question mark).

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

11) Select the best reagents for the reaction shown.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) 1. RCO3H; 2. H3O+

D) H2SO4, H2O

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

12) Select the best reagents for the reaction shown.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) 1. RCO3H; 2. H3O+

D) H2SO4, H2O

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

13) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CC1=CCC(C1)(C)C reacts with a reagent (represented with a question mark), to form the product that has a six-carbon chain, in which C-1 and C-5 are carbonyl group, and C-3 is single-bonded to two methyl groups.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) 1. RCO3H; 2. H3O+

D) H2SO4, H2O

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

14) Select the best reagents for the reaction shown.

A reaction shows the reactant that has a SMILES string of CC1=CCC(C1)(C)C reacts with a reagent (represented with a question mark) to form the product and an enantiomer.
The structure of the product has a cyclohexane ring, in which C-1 is single-bonded to two methyl groups, C-3 is dash-bonded to a hydroxyl group, O H, and wedge-bonded to a methyl group.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) 1. RCO3H; 2. H3O+

D) 1. BH3-THF; 2. H2O2, NaOH

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

15) Select the best reagents for the reaction shown.

A reaction shows the reactant that has a SMILES string of CC1=CCC(C1)(C)C reacts with a reagent (represented with a question mark) to form the product and an enantiomer.
The structure of the product has a cyclohexane ring, in which C-1 is single-bonded to two methyl groups, C-3 is wedge-bonded to a methyl group, and C-4 is dash-bonded to a methyl group.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) 1. RCO3H; 2. H3O+

D) 1. BH3∙THF; 2. H2O2, NaOH

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

16) Select the best reagents for the reaction shown.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) H2, Pt

D) 1. BH3∙THF; 2. H2O2, NaOH

E) 1. O3;2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

17) Select the best reagents for the reaction shown.

A reaction shows the reactant that has a seven-carbon chain, in which C-2 is single-bonded to a methyl group, and C-3 is triple-bonded to C-4. The reactant reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC/C=C/C(C)C.

A) 1. OsO4; 2. NaHSO3, H2O

B) NaNH2

C) H2, Pt

D) Na, NH3(l)

E) H2, Lindlar's catalyst

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

18) Select the best reagents for the reaction shown.

$A reaction shows the reactant that has a seven-carbon chain, in which C-2 is single-bonded to a methyl group, and C-3 is triple-bonded to C-4. The reactant reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC/C=C\C(C)C.$

A) 1. OsO4; 2. NaHSO3, H2O

B) NaNH2

C) H2, Pt

D) Na, NH3(l)

E) H2, Lindlar's catalyst

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

19) Select the best reagents for the reaction shown.

A reaction shows the reactant that has a five-carbon chain, in which C-1 is triple-bonded to C 2. C 3 is single bonded to a methyl group. The reactant reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC(C)CC=O.

A) 1. OsO4; 2. NaHSO3, H2O

B) 1. Hg(OAc)2, H2O; 2. NaBH4

C) H2, Pt

D) 1. 9-BBN; 2. H2O2, NaOH

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

20) Select the best reagents for the reaction shown.

A) 1. OsO4; 2. NaHSO3, H2O

B) H2SO4, H2O, HgSO4

C) H2, Pt

D) 1. 9-BBN; 2. H2O2, NaOH

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

21) Select the best reagents for the reaction shown.

A) 1. OsO4; 2. NaHSO3, H2O

B) H2SO4, H2O, HgSO4

C) NaOH

D) excess NaNH2

E) 1. O3; 2. DMS

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

22) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CC(C)CC#C reacts with a reagent (represented with a question mark), to form the product along with carbon dioxide, C O 2 as a by-product.
The structure of the product has a SMILES string of CC(C)CC(=O)O.

A) 1. OsO4; 2. NaHSO3, H2O

B) H2SO4, H2O, HgSO4

C) NaOH

D) excess NaNH2

E) 1. O3; 2. H2O

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

23) Select the best reagents for the reaction shown.

A) 1. OsO4; 2. NaHSO3, H2O

B) ROOR, heat

C) NaOH

D) excess NaNH2

E) 1. O3; 2. H2O

Diff: 2

Learning Objective: 11.1 Identify the reagents for a one-step synthesis

24) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string CC(C)CC#C reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CC(C)CC(=C)Br.

A) 1. OsO4; 2. NaHSO3, H2O

B) HBr, ROOR

C) NaBr

D) excess NaNH2

E) HBr

Diff: 3

Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group

25) Select the best reagent to convert 4,5-dimethylhex-2-yne to trans-4,5-dimethylhex-2-ene.

A) 1. OsO4; 2. NaHSO3, H2O

B) HBr, ROOR

C) NaBr

D) Na, NH3

E) HBr

Diff: 3

Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group

26) Select the best reagent to convert 1-bromo-1-methylcyclohexane to 1-bromo-2-methylcyclohexane.

A) 1. KOtBu; 2. HBr

B) 1. NaOEt; 2. HBr

C) 1. NaOEt; 2. HBr, ROOR

D) 1. KOtBu; 2. HBr, ROOR

E) Br2, hv

Diff: 3

Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group

27) Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methylcyclohexanol to a secondary position?

A) 1. KOtBu; 2. Hg(OAc)2, H2O; 3. NaBH4

B) 1. TsCl, pyr; 2. KOtBu; 3. BH3-THF; 4. H2O2, NaOH

C) 1. H2SO4, heat; 2. BH3-THF; 3. H2O2, NaOH

D) 1. TsCl, pyr; 2. NaOH; 3. BH3-THF; 4. H2O2, NaOH

E) C and D

Diff: 3

Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group

28) Which sequence of reagents will accomplish the synthesis shown?

A reaction shows the reactant with SMILES string CC(C)CCCBr reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CC(C)CC(C)Br.

A) 1. KOtBu; 2. HBr

B) 1. NaOEt; 2. HBr, ROOR

C) 1. H2SO4, heat; 2. Br2, hv

D) 1. NaOEt; 2. HBr

E) A and D

Diff: 3

Learning Objective: 11.2 Identify the reagents necessary to change the identity or position of a functional group

29) Which sequence of reagents will accomplish the synthesis shown?

A reaction shows the reactant that has a four-carbon chain, in which C-1 is triple-bonded to C 2. C 3 is single bonded to a methyl group. The reactant reacts with a reagent (represented with a question mark), to form the product that has a five-carbon chain, in which C-2 is single-bonded to a methyl group, and C-2 is triple-bonded to C-3.

A) 1. KOtBu; 2. 1-bromopropane

B) 1. NaNH2; 2. 1-bromopropane

C) 1. NaNH2; 2. 2-bromopropane

D) 1. O3; 2. DMS

E) 1. O3; 2. 1-bromopropane

Diff: 3

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

30) Predict the major product(s) for the reaction shown.

A reaction shows the reactant that has a cyclopropane ring, in which C-2 is single-bonded to a methyl group, and C-1 is single-bonded to a carbon atom that is further triple-bonded to a carbon atom. The reactant reacts first with sodium amide, N a N H 2, and second with iodomethane, C H 3 I to form the product (represented with a question mark).

A) I

B) II

C) III

D) IV

E) II and III

Diff: 2

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

31) Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.

A) hept-1-en-4-yne

B) hept-6-en-3-yne

C) hept-3-en-6-yne

D) hept-4-en-1-yne

E) hept-2-en-4-yne

Diff: 2

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

32) The reaction of compound A (molecular formula = C7H12) with sodium amide followed by 1-bromobutane produces a compound with the structure (CH3)2CHCH(CH3)CC(CH2)3CH3. What is compound A?

A) 2,3-dimethylnon-4-yne

B) 2,2-dimethylpent-1-yne

C) 3,4-dimethylpent-1-yne

D) 4,4-dimethylhept-1-yne

E) 1-heptyne

Diff: 2

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

33) The reaction of compound A (molecular formula = C12H24) with ozone followed by DMS produces only (CH3)3CCH2CHO. Which of the following could be compound A?

A) cis-2,3,7,8-tetramethyloct-4-ene

B) trans-dodec-6-ene

C) 4,4-dimethylpent-1-ene

D) cis-2,2,7,7-tetramethyloct-4-ene

E) 2,2-dimethyldec-4-ene

Diff: 2

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

34) Select the best reagents for the reaction shown.

A reaction shows the reactant with SMILES string C1CCCCC#CCCC1 reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of C(CCCCC(=O)O)CCCC(=O)O.

A) NaNH2

B) 1. O3; 2. H2O

C) KMnO4

D) 1. BH3-THF; 2. H2O2, NaOH

E) H2SO4, H2O

Diff: 2

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

35) Compound X has the molecular formula C8H10. The reaction of compound X with excess ozone, followed by reaction of the product with dimethyl sulfide and then washing with water produces only the compounds shown. Which compound below could be for compound X that is consistent with these results.

A reaction shows the reactant, Compound X that has a molecular formula of C 8 H 10 reacts first with ozone, O 3, second with D M S, and third with water, H 2 O to form two products.
The structure of the first product has a SMILES string of C(C=O)C(CC=O)C(=O)O.
The structure of the second product has a SMILES string of CC(=O)O.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 3

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

36) Predict the products of the reaction shown.

A reaction shows the reactant that has a SMILES string of CC(=CC#C)C reacts first with ozone, O 3, second with dimethyl sulfide, D M S, and third with water, H 2 O to form the product (represented with a question mark).

A) I, III, and IV

B) II, III, and IV

C) I, III, and V

D) II, IV, and VI

E) III and IV

Diff: 3

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

37) What single compound is produced when acetylene is treated with the reagents below?

A reaction shows the reactant that has a SMILES string of C#C reacts first with sodium amide, N a N H 2, second with 1-bromopropane, third with sodium amide, N a N H 2, fourth with 1-bromopropane, fifth with ozone, and sixth with water to form the product (represented with a question mark).

A) butanoic acid

B) propanoic acid

C) 1,6-bromohexane

D) ethylene

E) acetaldehyde

Diff: 3

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

38) Predict the sequence of reactants required to complete the following synthesis in which propanal is the only carbon-containing product.

A reaction shows the reactant with SMILES string CCC#C, which reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC=O.

NaNH2	CH3SCH3	H2O	CH3CH2Br	O3	Na/NH3(l)	H2/Pt
I	II	III	IV	V	VI	VII

A) 1. I; 2. III; 3. IV; 4. V; 5. II

B) 1. VI; 2. IV; 3. IV; 4. VII; 5. V; 6. II

C) 1. V; 2. II

D) 1. I; 2. IV; 3. VI; 4. V; 5. II

E) none of the above are correct

Diff: 3

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

39) Propose a synthesis of propanoic acid from acetylene.

A) 1. Br2/CCl4; 2. xs NaNH2; 3. H2O

B) t-BuOk followed by 1. Hg(OAc)2, H2O; 2. NaBH4

C) 1. NaNH2; 2. CH3CH2Br followed by 1. O3; 2. H2O

D) 1. BH3/THF; 2. H2O2, NaOH

E) NaOEt followed by 1. BH3/THF; 2. H2O2, NaOH

Diff: 3

Learning Objective: 11.3 Identify the reagents necessary to change the carbon skeleton of a molecule

40) Which synthesis will yield cyclopentanone from 1-methylcyclopentane?

A reaction shows the reactant with SMILES string of CC1CCCC1 that reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of C1CCC(=O)C1.

A) t-BuOk followed by 1. Hg(OAc)2, H2O; 2. NaBH4

B) 1. Br2/CCl4; 2. xs NaNH2; 3. H2O

C) t-BuOk followed by 1. Hg(OAc)2 , H2O3 2. NaBH4

D) Br2/ hv, followed by KOtBu, followed by 1. O3; 2. DMS

E) NaOEt followed by 1. Hg(OAc)2, H2O; 2. NaBH4

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

41) Identify the changes that must occur to convert cis-2-butene into 2-butanol.

A) only the identity of the functional group(s) must change

B) only the carbon skeleton must change

C) only the location of the functional group(s) must change

D) only the identity and location of the functional group(s) must change

E) both the carbon skeleton and the identity of the functional group(s) must change

Diff: 2

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

42) Which choice will synthesize 1-butene from propyne?

A two-step reaction is as follows:
The first step shows the reactant that has a SMILES string of CC#C yields an intermediate compound.
The structure of the intermediate compound has a SMILES string of CC#CC.
The second step shows the intermediate compound yielding a product that has a SMILES string of CCC=C.

A) 1. NaNH2; 2. CH3I followed by 1. NaNH2; 2. H2O; 3. H2/Lindlar's catalyst

B) 1. BH3/THF; 2. H2O2; NaOH

C) H2/Pt, then NaOH

D) CH3I followed by H2/Pt

E) HBr/ROOR; 2. NaOH

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

43) The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1) and then from that product into a compound in which the functional group has been changed (compound 2). Identify compounds 1 and 2.

A) Compound 1 = I; Compound 2 = III

B) Compound 1 = II; Compound 2 = III

C) Compound 1 = VI; Compound 2 = IV

D) Compound 1 = II; Compound 2 = IV

E) Compound 1 = II; Compound 2 = V

F) Compound 1 = VII; Compound 2 = VIII

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

44) Which of the following sequences converts 2-methylpropene and sodium acetylide into 3-methylbutanal?

A reaction shows the reactant with SMILES string CC(=C)C that reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CC(C)CC=O.

A) 1. HBr; 2. NaCCH; 3. O3; 4. H2O

B) 1. HBr; 2. NaCCH; 3. O3; 4. DMS

C) 1. HBr, ROOR; 2. NaCCH; 3. O3; 4. H2O

D) 1. HBr, ROOR; 2. NaCCH; 3. H2/Ni2B; 4. O3; 5. DMS

E) 1. NaCCH; 2. H2/Ni2B; 3. O3; 4. DMS

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

45) Which of the following sequences converts 3-methyl-1-pentene into 3-bromo-3-methylpentane?

A) 1. Br2; 2. NaOH; 3. HBr

B) 1. Br2, hv; 2. H2, Pt

C) 1. H2, Pt; 2. Br2, hv

D) 1. NBS, hv; 2. H2, Pt

E) 1. HBr, ROOR; 2. NaOH; 3. HBr

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

46) Propose a synthesis to produce the following answer as one of the major products.

$A reaction shows the reactant with SMILES string of CCC(C)(C)/C=C\C reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC(C)(C)CCCC(=O)O.$

A) 1. CH3BH; 2. H2O2, NaOH

B) 1. H2, Lindlar's catalyst; 2. NaCCH; 3. excess O3; 4. H2O

C) 1. NBS, hv; 2. H2, Pt; 3. NaCCH; 4. excess O3

D) 1. NBS, hv; 2. H2, Pt; 3. NaCCH; 4. 1 equiv. O3; 5. H2O

E) 1. NBS, hv; 2. H2, Pt; 3. NaCCH; 4. H2O

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

47) Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.

A reaction shows the reactant with SMILES string CC(C)C(C)O reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CC(C)CCO.

A) 1. H3O+; 2. KOtBu; 3. H2O2, NaOH

B) 1. BH3-THF; 2. H2O2, NaOH

C) 1. TsCl, pyr; 2. BH3-THF; 3. H2O2, NaOH

D) 1. TsCl, pyr; 2. KOtBu; 3. BH3-THF; 4. H2O2, NaOH

E) 1. KOtBu; 2. BH3-THF; 3. H3O+

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

48) Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.

In a reaction, the reactant has a SMILES string CC(C)CCO. The product has a SMILES string of CC(C)C(C)O.

A) 1. NaOH; 2. H3O+

B) 1. H2SO4, heat; 2. NaBH4; 3. H3O+

C) 1. H2SO4, heat; 2. Hg(OAc)2, H2O; 3. NaBH4

D) 1. Hg(OAc)2, H2O; 2. H2SO4, heat; 3. NaBH4

E) 1. NaOMe; 2. BH3-THF; 3. H2O2, NaOH

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

49) Which of the following alkenes cannot be converted into an alkyne by reacting it with bromine followed by an excess of sodium amide and then with water?

The bond-line structure of four compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CCC=C.
The second compound has a SMILES string of CC(C)C=C.
The third compound has a SMILES string of C/C=C/C.
The fourth compound has a SMILES string of CC=C(C)C.

A) I

B) II

C) III

D) IV

E) III and IV

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

50) Which of the following provides a synthetic route to convert 3-bromo-2-methyl-1-butene into 2-methyl-2-butene?

A) 1. NaOH; 2. H2, Pt

B) 1. H2, Pt; 2. NaOEt

C) 1. H2, Pt; 2. Br2

D) 1. H2, Ni2B; 2. KOtBu

E) 1. H2, Pt; 2. KOtBu

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

51) Which order of reactions would most effectively convert trans-2-butene into 1-butene?

A) convert to the gem-dibromoalkane, then to the terminal alkyne, then to the terminal alkene

B) convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene

C) convert to the terminal alkene in one step

D) shorten the chain by two carbons, then add a two-carbon alkene to the end

E) convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene

Diff: 2

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

52) What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

53) What is the minimum number of steps required to convert 2-methylpropane into 1-bromo-2-methyl-2-propanol?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

54) Which synthetic route(s) would complete the reaction shown?

A reaction shows the reactant that has a SMILES string of C1CCC(C1)CBr reacts with a reagent (represented with a question mark), to form the product and an enantiomer.
The structure of the product has a cyclopentane ring, in which C-1 is bonded to a four-carbon chain, in which C-2 and C-3 are each wedge-bonded to a hydroxyl group, O H.

Synthesis I: 1. NaCCCH3; 2. Na/NH3(l) ;3. OsO4; 4. NaHSO3, H2O

Synthesis II: 2. NaCCCH3; 2. H2, Lindlar’s catalyst; 3. MCPBA; 4. aq. H2SO4

Synthesis III: 1. NaCCCH3; 2. H2, Pt; 3. MCPBA; 4. aq. H2SO4

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

55) Select the appropriate synthetic route for the equation shown.

A reaction shows the reactant with SMILES string CC1CCC(C1)C reacts with a reagent (represented with a question mark), to form the product that has a cyclopentane ring, in which C-1 is bonded to a methylene group that is further bonded to a sulfur atom. The sulfur atom is further bonded to another methyl group. C-3 of the cyclopentane ring is single-bonded to a methyl group.

A) 1. Br2; 2. KOtBu; 3. HBr, ROOR; 4. NaSMe

B) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. NaSH

C) 1. Br2, hv; 2. KOtBu; 3. NaSMe

D) 1. Br2, hv; 2. KOtBu; 3. NaSH; 4. H3O+

E) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. NaSMe

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

56) Select the appropriate synthetic route for the reaction shown.

A reaction shows the reactant with SMILES string C1CCC(C1)Br reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CSC1CCC=C1.

A) 1. NBS; 2. NaOEt; 3. NaSMe

B) 1. NaOEt; 2. NBS; 3. NaSMe

C) 1. NaOEt; 2. NBS; 3. NaSH

D) 1. NaBr; 2. NBS, hv; 3. NaSMe

E) 1. NaOEt; 2. NBS, hv; 3. NaSMe

Diff: 3

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

57) Select the appropriate synthetic route for the reaction shown.

A reaction shows the reactant with SMILES string CC/C=C/CC that reacts with a reagent (represented with a question mark), to form the product that has a SMILES string of CCC(=O)O.

A) 1. O3, H3O+

B) 1. H2, Lindar's; 2. O3, H3O+

C) 1. Br2, CCl4; 2. excess NaNH2; 3. H2O; 4. O3; 5. H2O

D) 1. H2O, H2SO4, HgSO4; 2. excess NaNH2; 3. H2O; 4. O3; 5. H2O

E) 1. Br2, CCl4; 2. O3; 3. H2O; 4. excess NaNH2; 5. H2O

Diff: 2

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

58) Select the appropriate synthetic route for the reaction shown.

A reaction shows the reactant with SMILES string C1CC1CCBr reacts to form the product that has a cyclopropane ring, in which C-1 is bonded to a four-carbon chain. In the four-carbon chain, C-4 is a carbonyl group.

A) 1. NaCCH; 2. 9-BBN; 3. H2O2, NaOH

B) 1. R2BH; 2. H2O, NaOH; 3. H2O2, NaOH

C) 1. xs NaNH2; 2. H2O; 3. O3; 4. H2O

D) 1. NaCCH; 2. H2O2; 3. 9-BBN; 4. NaOH

E) 1. 9-BBN; 2. NaCCH; 3. H2O2, NaOH

Diff: 2

Learning Objective: 11.4 Propose a synthesis, considering change of carbon skeleton, and of identity or position of a functional group

59) Using retrosynthetic synthesis, determine which compound(s) could lead to the alkene shown in a single step.

In a retrosynthetic analysis, the target molecule that has a SMILES string of C=CC1CC1 converts to a starting material (represented with a question mark).

The bond-line structure of four compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of BrC(C)C1CC1.
The second compound has a SMILES string of CC(C)C1CC1.
The third compound has a SMILES string of CCC1CC1.
The fourth compound has a SMILES string of C#CC1CC1.

A) I

B) II

C) III

D) IV

E) I or IV

F) I, III, or IV

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

60) Using retrosynthetic synthesis, determine which compound(s) could lead to the alcohol shown in a single step.

In a retrosynthetic analysis, the target molecule that has a SMILES string of CC(C)C(C)O converts to a starting material (represented with a question mark).

The bond-line structure of four compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(C)C=C.
The second compound has a SMILES string of CC=C(C)C.
The third compound has a SMILES string of CCC(C)C.
The fourth compound has a SMILES string of CC(C)C#C.

A) I

B) II

C) III

D) IV

E) I or II

F) I, II, or IV

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

61) Using retrosynthetic synthesis, determine which compound(s) could lead to the alkyne shown in a single step.

In a retrosynthetic analysis, the target molecule that has a SMILES string of CC(C)C#C converts to a starting material (represented with a question mark).

The bond-line structure of four compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(C)C=C.
The second compound has a SMILES string of CC(C)C(C)Br.
The third compound has a SMILES string of CC(C)C(Br)Br.
The fourth compound has a SMILES string of CC(C)C(CBr)Br.

A) I

B) II

C) III

D) IV

E) I or II

F) I, II, or IV

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

62) Using retrosynthetic synthesis, determine which compound(s) could lead to the alkane shown in a single step.

In a retrosynthetic analysis, the target molecule that has a SMILES string of CCC(C)C converts to a starting material (represented with a question mark).

The bond-line structure of four compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(C)C=C.
The second compound has a SMILES string of CC(C)C(C)Br.
The third compound has a SMILES string of CC(C)C(C)O.
The fourth compound has a SMILES string of CC(C)C#C.

A) II or III

B) I or IV

C) I

D) III

E) IV

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

63) Using retrosynthetic synthesis, determine which compound(s) could lead to the bromoalkene shown in a single step.

In a retrosynthetic analysis, the target molecule that has a SMILES string of CC(=C)CBr converts to a starting material (represented with a question mark).

The bond-line structure of four compounds labeled 1 through 4 (in Roman Numerals) are as follows:
The first compound has a SMILES string of CC(=C)C.
The second compound has a SMILES string of CCC(C)CBr.
The third compound has a SMILES string of CC(C)(C)O.
The fourth compound has a SMILES string of CCC(=C)C.

A) I or III

B) I or IV

C) I

D) II

E) III

F) IV

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

64) Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that could lead to the alkyl halide (C).

A two-step retrosynthetic analysis is as follows:
The first step shows the target molecule with SMILES string CC(C1CCCC1)Br converts to the intermediate, compound B.
The second step sows the intermediate, compound B further converts to the starting material, compound A.

A) B = I and A = VIII

B) B = VI and A = I

C) B = III and A = VII

D) B = IV and A = VII

E) B = V and A = VIII

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

65) Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that can lead to the alkyne (C).

A two-step retrosynthetic analysis is as follows:
The first step shows the target molecule with SMILES string C#CC1CCCC1 converts to the intermediate, compound B.
The second step sows the intermediate, compound B further converts to the starting material, compound A.

A) B = I and A = VI

B) B = VI and A = I

C) B = III and A = VII

D) B = IV and A = VII

E) B = VI and A = VIII

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

66) Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that can lead to the alcohol (C).

A two-step retrosynthetic analysis is as follows:
The first step shows the target molecule with SMILES string CCC1(CCCC1)O converts to the intermediate, compound B.
The second step sows the intermediate, compound B further converts to the starting material, compound A.

A) B = I and A = VI

B) B = VI and A = I

C) B = III and A = VII

D) B = VII and A = II

E) B = VIII and A = V

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

67) Perform a retrosynthetic analysis by working backwards two steps in the given synthesis. Identify possible combinations of A and B that can lead to the compound shown (C).

A) B = I and A = VI

B) B = V and A = II

C) B = IV and A = VII

D) B = I and A = III

E) B = VIII and A = V

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

68) Perform a retrosynthetic analysis by working backwards two steps in the synthesis shown. Identify possible combinations of A and B that can lead to the alkene (C).

$A two-step retrosynthetic analysis is as follows: The first step shows the target molecule with SMILES string C/C=C\CCC(C)C converts to the intermediate, compound B. The second step sows the intermediate, compound B further converts to the starting material, compound A.$

A) B = I and A = IV

B) B = II and A = VI

C) B = III and A = I

D) B = I and A = VI

E) B = III and A = II

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

69) Select the appropriate synthetic route to convert methylcyclobutane into cyclopentene.

A reaction shows the reactant with SMILES string of CC1CCC1 that reacts with reagents (represented with two question marks), to form the product that has a SMILES string of C1CC=CC1.

A) 1. KOtBu; 2. BH3-THF; 3. H2O2, NaOH; 4: H2SO4, heat

B) 1. H2, Lindlar's catalyst; 2. BH3-THF; 3. H2O2, NaOH

C) 1. Br2, hv; 2. KOtBu; 3. BH3-THF; 4. H2O2, NaOH; 5: H2SO4, heat

D) 1. BH3-THF; 2. H2O2, NaOH; 3. H2, Pt

E) 1. Br2, hv; 2. KOtBu; 3. H2O2, NaOH; 4: H2SO4, heat

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

70) Select the appropriate synthetic route to convert ethylene into PVC (polyvinyl chloride).

A) 1. Br2; 2. excess NaNH2; 3. H2O; 4. 1 eq. HCl; 5. ROOR, heat

B) 1. Br2; 2. 1 equivalent NaNH2; 3. H3O+; 4. 1 eq. HCl; 5. ROOR

C) 1. Cl2; 2. 1 equivalent NaNH2; 3. H3O+; 4. 1 eq. HCl; 5. ROOR

D) 1. Br2, CCl4; 2. Na, NH3(l)

E) 1. Cl2; 2. excess NaNH2; 3. H2O; 4. ROOR, heat

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

71) Select the appropriate method of converting acetylene into the polymer shown.

A reaction shows the reactant with SMILES string of C#C that reacts with reagents (represented with two question marks) to form the product that has a repeating unit of a two-carbon chain, in which C-1 is single-bonded to a chlorine atom, C l, and a methyl group.

A) 1. NaNH2; 2. CH3Cl; 3. ROOR, heat

B) 1. CH3Br; 2. excess HCl; 3. ROOR, heat

C) 1. NaNH2; 2. CH3Br; 3. excess HCl; 4. ROOR

D) 1. NaNH2; 2. CH3Br; 3. HCl (1 equiv.); 4. ROOR, heat

E) 1. CH3Cl; 2. NaNH2; 3. CCl4; 4. ROOR, heat

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

72) Select the appropriate synthetic route to convert 5-methyl-1-hexene into 5-methylhexanal.

A) 1. Br2; 2. H2O; 3. Disiamylborane; 4. H2O2, NaOH

B) 1. O3; 2. H2O; 3. excess NaNH2; 4. H2O

C) 1. Br2; 2. H2O; 3. Disiamylborane; 4. NaOH

D) 1. Br2; 2. excess NaNH2; 3. H2O; 4. Disiamylborane; 5. H2O2, NaOH

E) 1. Cl2; 2. excess NaNH2; 3. H2O; 4. H2O2, NaOH

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

73) Select the appropriate method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

A) 1. CCl4; 2. excess NaNH2; 3. O3; 4. H2O

B) 1. Br2, CCl4; 2. excess NaNH2; 3. H2O

C) 1. Cl2, CCl4; 2. NaNH2; 3. H2O; 4. O3; 5. H2O

D) 1. O3; 2. H2O; 3. CCl4; 4. excess NaNH2; 5. H2O

E) 1. Br2, CCl4; 2. excess NaNH2; 3. H2O; 4. O3; 5. H2O

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

74) Which of the reactions shown effectively produces 4,4-dimethyl-2-pentyne?

$The four partial reactions labeled 1 through 4 (in Roman Numerals0 are as follows: The first reaction shows the reactant that has a SMILEs string of CC(C)(C)Br reacts with N a C C C H 3. The second reaction shows the reactant that has a SMILES string of CC(C)(C)C#C (one of the triple-bonded carbon atoms carries a negative charge) reacts with bromomethane, C H 3 B r. The third reaction shows the reactant that has a five-carbon chain, in which C-3 is single-bonded to two bromine atoms, and C-4 is single-bonded to two methyl groups reacts with two molecules of sodium amide, N a N H 2. The fourth reaction shows the reactant that has a SMILES string of C/C(/Br)=C\C(C)(C)C reacts with one molecule of sodium amide, N a N H 2.$

A) I, II, III, and IV

B) II, III, and IV

C) I, II, and III

D) I, II, and IV

E) I, III, and IV

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

75) Select an appropriate synthetic route to yield the given diol starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

A reaction shows the first reactant that has a cyclohexane ring, in which C-1 and C-3 are each single-bonded to two methyl groups, and C-2 is bonded to a three-carbon chain, In the three-carbon chain, C-1 is dash-bonded to a hydroxyl group, O H, and C-2 is wedge-bonded to hydroxyl group O H. The first reactant reacts with an enantiomer.

A) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. RCO3H; 10. H3O+

B) 1. Br2, hv 2. HBr, ROOR; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Cl; 8. H2, Pd; 9. OsO4, NMO; 10. H3O+

C) 1. Br2, hv; 2. HBr, ROOR; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. NaHSO3, H2O

D) 1. Br2, hv; 2. HBr; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O

E) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

76) Select an appropriate synthetic route of the diol shown starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

A reaction shows the first reactant that has a cyclohexane ring, in which C-1 and C-3 are single-bonded to two methyl group, and C-2 is bonded to a three-carbon chain, In the three-carbon chain, C-1 and C-2 are wedge-bonded to hydroxyl group O H. The first reactant reacts with an enantiomer.

A) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. RCO3H; 10. H3O+

B) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Pt; 9. OsO4, NMO; 10. NaHSO3, H2O

C) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. 1 equiv. NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4; 10. H3O+

D) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O

E) 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Pd; 9. RCO3H; 10. H3O+

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

77) Select an appropriate synthetic route of the compound shown starting with 4-methyl-2-pentanol.

In a retrosynthetic analysis, the target molecule that has a SMILES string of CC(C)CCCOC(=O)C converts to a starting material that has a SMILES string of CC(C)CC(C)O.

A) 1. TsCl, pyr; 2. KOtBu; 3. HCl/ROOR; 4. The bond-line structure of a compound has a central carbon atom, that is single-bonded to a methyl group on the left side, single-bonded to a hydroxyl group, O H on the top, and single-bonded to an O N a group on the right side.

B) 1. TsCl, pyr; 2. KOtBu; 3. HBr/ROOR; 4. The bond-line structure of a compound has a central carbon atom, that is single-bonded to a methyl group on the left side, single-bonded to a hydroxyl group, O H on the top, and single-bonded to an O N a group on the right side.

C) 1. TsCl, pyr; 2. KOtBu; 3. HBr; 4. H3O+; 5. The bond-line structure of a compound has a central carbon atom, that is single-bonded to a methyl group on the left side, double-bonded to an oxygen atom, O on the top, and single-bonded to an O N a group on the right side.

D) 1. TsCl, pyr; 2. KOtBu; 3. HBr/ROOR; 4. The bond-line structure of a compound has a central carbon atom, that is single-bonded to a methyl group on the left side, double-bonded to an oxygen atom, O on the top, and single-bonded to an O N a group on the right side.

E) 1. TsCl, pyr; 2. KOtBu; 3. HBr/ROOR; 4. The bond-line structure of a compound has a central carbon atom, that is double-bonded to a methylene group on the left side, single-bonded to a hydroxyl group, O H on the top, and single-bonded to an O N a group on the right side.

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

78) Starting with a primary alkyl bromide, which of the choices given results in an overall increase in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond

B) substitute bromide with acetylide, then reduce the alkyne to an alkene

C) substitute bromide with methoxide

D) eliminate hydrogen bromide to produce an alkene

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

79) Starting with a primary alkyl bromide, which of the choices given results in an overall decrease in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond

B) substitute bromide with acetylide, then reduce the alkyne to an alkene

C) substitute bromide with methoxide

D) eliminate hydrogen bromide to produce an alkene, then cleave the double bond

Diff: 2

Learning Objective: 11.5 Perform a retrosynthetic analysis

80) Select an appropriate synthetic route for the following equation.

A) 1. NaOH; 2. BH3-THF; 3. NaOH

B) 1. BH3-THF; 2. H3O+

C) 1. NaOEt; 2. H2O2, NaOH

D) 1. NaBr; 2. BH3-THF; 3. H2O2, NaOH

E) 1. NaOEt; 2. BH3-THF; 3. H2O2, NaOH

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

81) Select an appropriate synthetic route for the equation given.

In a retrosynthetic analysis, the target molecule that has a SMILES string of C[C@@H]1[C@@H](O1)C converts to a starting material, acetylene.

A) 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar’s catalyst; 6. H3O+

B) 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar’s catalyst; 6. RCO3H

C) 1. NaNH2; 2. CCl4; 3. NaNH2; 4. CH3Br; 5. H2, Pd; 6. RCO3H

D) 1. NaNH2; 2. CCl4; 3. NaNH2; 4. CH3Br; 5. H2, Lindlar’s catalyst; 6. RCO3H

E) 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. H2, Pt; 6. RCO3H

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

82) Select an appropriate synthetic route for the equation given.

In a retrosynthetic analysis, the target molecule that has a SMILES string of C[C@@H]1[C@H](O1)C converts to a starting material, acetylene.

A) 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. OsO4; 6. H3O+

B) 1. MCPBA; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. Na, NH3(l); 6. RCO3H

C) 1. MCPBA; 2. CH3Br r; 3. NaNH2; 4. CH3Br; 5. OsO4; 6. H3O+

D) 1. NaNH2; 2. CH3Br; 3. NaNH2; 4. CH3Br; 5. Na, NH3 (l); 6. RCO3H

E) 2. CH3Br; 2. NaNH2; 3. CH3Br; 4. Na, NH3(l); 5. RCO3H

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

83) Select an appropriate synthetic route for the equation given.

In a retrosynthetic analysis, the target molecule that has a SMILES string of C(CC#N)CC#N converts to a starting material, that has a SMILES string of CC=C.

A) 1. NBS, hv; 2. HBr, ROOR; 3. N2

B) 1. NBS, hv; 2. HBr, ROOR; 3. NaCN

C) 1. Br2, hv; 2. HBr, ROOR; 3. 2 NaCN

D) 1. NBS, hv; 2. HBr; 3. 2 NaCN

E) 1. NBS, hv; 2. HBr, ROOR; 3. 2 NaCN

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

84) Select an appropriate synthetic route to prepare 1,7-heptanediol from propene.

A) 1. HBr, ROOR; 2. 2 NaCCH; 3. H2, Lindlar’s catalyst; 4. BH3-THF; 5. H2O2, NaOH

B) 1. NBS, light; 2. HBr; 3. 2 NaCCH; 3. H2, Lindlar’s catalyst; 5. BH3-THF; 6. H2O2, NaOH

C) 1. NBS, light; 2. HBr, ROOR; 3. 2 NaCCH; 3. H2, Pt; 5. BH3-THF; 6. H2O2, NaOH

D) 1. HBr; 2. 2 NaCCH; 3. H2, Lindlar’s catalyst; 4. BH3-THF; 5. H2O2, NaOH

E) 1. NBS, light; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Lindlar’s catalyst; 5. BH3-THF; 6. H2O2, NaOH

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

85) Select an appropriate synthetic route to prepare 1,3-dibromopropan-2-ol from propene.

A) 1. NBS, light; 2. Br2, H2O

B) 1. NBS; 2. Br2; 3. H3O+

C) 1. BH3-THF; 2. H2O2, NaOH; 3. Br2, H2O

D) Br2, H3O+

E) Br2, H2O

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

86) Select an appropriate synthetic route to prepare 3-bromo-1-propanol from propene.

A) 1. BH3-THF; 2. H2O2, NaOH

B) 1. NBS, light; 2. BH3-THF; 3. H2O2

C) 1. NBS, light; 2. BH3-THF; 3. H2O2, ROOR

D) 1. NBS; 2. BH3-THF; 3. H2O2, NaOH

E) 1. NBS, light; 2. BH3-THF; 3. H2O2, NaOH

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

87) Select an appropriate synthetic route for the equation given.

In a retrosynthetic analysis, the target molecule that has a cyclopentane ring, in which C-1 is bonded to a methyl group, and C-1 is also bonded to a three-carbon chain: In the three-carbon chain, C-1 is double-bonded to a methylene group, and C-3 is triple-bonded to a nitrogen atom converts to a starting material, that has a SMILES string of CC(=C)C1(CCCC1)C.

A) 1. NBS; 2. KCN

B) 1. NBS, hv; 2. CH3CN

C) 1. NBS, hv; 2. KCN

D) 1. H2SO4; 2. KCN

E) 1. NaCN, hv

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

88) Select an appropriate synthesis to lengthen the legs of "Ralph" as shown.

A) 1. NBS, hv; 2. KCN; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Lindlar’s catalyst

B) 1. NBS; 2. KCN; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Lindlar’s catalyst

C) 1. NBS, hv; 2. KCN; 2. HBr; 3. 2 NaCCH; 4. H2, Pt

D) 1. NBS, hv; 2. NaCN; 2. HCl, ROOR; 3. 2 NaCCH; 4. H2, Pt

E) 1. NBS, hv; 2. HBr, ROOR; 3. 2 NaCCH; 4. H2, Pt

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

89) Select an appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CC1CCCC1 reacts to form the product that has a SMILES string of CC1CCCC1Br.

A) 1. Br2; 2. NaOEt; 3. HBr, ROOR

B) 1. Br2, hv; 2. NaOEt; 3. HBr

C) 1. Br2, hv; 2. HBr, ROOR

D) 1. Br2, hv; 2. NaOEt; 3. HBr, ROOR

E) 1. Br2, hv; 2. NaOEt

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

90) Select the appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CC1CCCC1Br reacts to form the product that has a SMILES string of C=C1CCCC1.

A) 1. NaOEt; 2. HBr

B) 1. NaOEt; 2. HBr; 3. KOtBu

C) 1. HBr; 2. KOtBu

D) 1. NaOEt; 2. Br2; 3. KOtBu

E) 1. NaOEt; 2. Br2, hv

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

91) Select the appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CC1(CCCC1)O reacts to form the product that has a SMILES string of C1CCC(C1)CBr.

A) 1. KOtBu; 2. HBr, ROOR

B) 1. TsCl; 2. KOtBu; 3. Br2

C) 1. TsCl; 2. KOtBu; 3. HBr

D) 1. KOtBu; 2. TsCl; 3. HBr, ROOR

E) 1. TsCl; 2. KOtBu; 3. HBr, ROOR

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

92) Select an appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CC1CCCC1 reacts to form the product that has a SMILES string of C1CCC2(C1)CO2.

A) 1. HBr/ROOR; 2. excess NaNH2

B) 1. Br2, hv; 2. KOtBu; 3. ROOR

C) 1. Br2; 2. KOtBu; 3. MCPBA

D) 1. Br2, hv; 2. KOtBu; 3. H3O+

E) 1. HBr; 2. KOtBu; 3. MCPBA

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

93) Propose a multi-step synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CC1CCCC1 reacts to form a product and an enantiomer.
The structure of the product has a cyclopentane ring, in which C-1 is dash-bonded to a methyl group, and wedge-bonded to a hydroxyl group, O H, and C-2 is wedge-bonded to a hydroxyl group, O H.

A) 1. Br2, hv; 2. NaOEt; 3. OsO4, NMO

B) 1. HBr; 2. NaOEt; 3. OsO4, NMO

C) 1. Br2, hv; 2. NaOCH3; 3. OsO4

D) 1. HBr; 2. NaOCH3; 3. OsO4, NMO

E) 1. Br2, hv; 2. NaOEt; 3. NMO

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

94) Select the appropriate multi-step synthetic sequence to accomplish the transformation shown.

A) 1. HBr; 2. NaOEt; 3. MCPBA; 4. H3O+

B) 1. HBr; 2. NaOEt; 3. H3O+

C) 1. Br2, hv; 2. NaOEt; 3. H3O+

D) 1. Br2, hv; 2. NaOEt; 3. MCPBA; 4. H3O+

E) 1. Br2, hv; 2. NaOEt; 3. H2SO4; 4. H3O+

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

95) Select the appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CC1(CCCC1)O reacts to form the product that has a SMILES string of CC1CCCC1SC.

A) 1. H2SO (1 equiv.); 2. Br2, ROOR; 3. NaSCH3

B) 1. Conc. H2SO4; 2. Br2, ROOR; 3. NaSCH3

C) 1. Conc. H2SO4; 2. HBr; 3. NaSCH3

D) 1. Conc. H2SO4; 2. HBr, ROOR; 3. NaSCH3

E) 1. Conc. H2SO4; 2. HBr, ROOR

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

96) Select the appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant that has a cyclopentane ring, in which C-1 is single-bonded to a methyl group and a bromine atom that converts to the product that has a cyclopentane ring, in which C-1 is bonded to a five-carbon chain. In the five-carbon chain, C-2 is triple-bonded to C-3.

A) 1. KOtBu; 2. Br2. hv; 3. CH3CH2CCNa

B) 1. KOtBu; 2. HBr, ROOR; 3. CH3CH2CMgBr

C) 1. KOtBu; 2. HBr; 3. CH3CH2CCNa

D) 1. KOtBu; 2. HBr, ROOR; 3. CH3CH2CCNa

E) 1. KOtBu; 2. HBr, ROOR; 3. H3O+

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

97) Select the appropriate synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CCCC(C)C reacts to form the product that has a SMILES string of CCC(C(C)C)O.

A) 1. HBr; 2. NaOEt; 3. BH3-THF; 4. HOOH, NaOH

B) 1. Br2, hv; 2. NaOEt; 3. HOOH, NaOH

C) 1. Br2, hv; 2. NaOEt; 3. BH3-THF; 4. NaOH

D) 1. Br2, hv; 2. NaOEt; 3. BH3-THF; 4. HOOH, NaOH

E) 1. Br2, hv; 2. NaOEt; 3. BH3-THF; 4. H2SO4; 5. HOOH, NaOH

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

98) Select the synthetic sequence to accomplish the transformation shown.

A reaction shows the reactant with SMILES string CCCC(C)C reacts to form two products.
The structure of the first product has a SMILES string of CCCC(=O)C.
The structure of the second product has a central carbonyl carbon, the carbon atom is single-bonded to two hydrogen atoms.

A) 1. HBr; 2. KOtBu; 3. O3; 4. DMS

B) 1. Br2, hv; 2. KOtBu; 3. O3; 4. DMS

C) 1. HBr; hv; 2. O3; 3. DMS

D) 1. Br2, hv; 2. KOtBu; 3. O3

E) 1. Br2, hv; 2. O3; 3. DMS

Diff: 3

Learning Objective: 11.5 Perform a retrosynthetic analysis

99) Which statement is not associated with Green Chemistry?

A) Maximize atom economy.

B) Use safer solvents.

C) Prevent waste.

D) Run all reactions faster with high heat.

E) Use less hazardous reagents.

Diff: 1

Learning Objective: 11.6 Define the goals of green chemistry

100) Which statement is not associated with Green Chemistry?

A) Energy efficiency.

B) Renewable feedstocks.

C) Reuse solvents without purification.

D) Prevent waste.

E) Use catalysts, rather that stoichiometric reagents.

Diff: 1

Learning Objective: 11.6 Define the goals of green chemistry

101) Which solvent is not recommended for Green Chemistry?

A) methylene chloride

B) water

C) ethanol

D) methanol

E) ethyl acetate

Diff: 1

Learning Objective: 11.6 Define the goals of green chemistry

102) Which solvent is best for Green Chemistry?

A) methylene chloride

B) water

C) ethanol

D) methanol

E) ethyl acetate

Diff: 1

Learning Objective: 11.6 Define the goals of green chemistry

103) Which of the methods shown is best for multi-step reactions?

A) two steps

B) three steps

C) four steps

D) five steps

E) six steps

Diff: 1

Learning Objective: 11.7 Prepare your own synthesis problems

104) Most synthesis problems have ________ correct answers.

A) no

B) one

C) two

D) four

E) many

Diff: 1

Learning Objective: 11.7 Prepare your own synthesis problems

105) Taxol is a powerful ________.

A) laxative

B) pain-killer

C) birth-control pill

D) anti-cancer drug

E) hallucinogen

Diff: 1

Learning Objective: 11.7 Prepare your own synthesis problems

106) Taxol is found in the ________ tree

A) tea

B) eucalyptus

C) sausage fruit

D) baobab

E) Pacific yew

Diff: 1

Learning Objective: 11.7 Prepare your own synthesis problems

107) Through a multistep synthesis, 1-bromo-2-methylcyclopentane can be converted to a compound with exactly four resonances in its proton-decoupled 13C NMR spectrum. Which synthetic pathway would prepare such a compound from 1-bromo-2-methylcyclopentane?

A) 1. KOEt; 2. H2, Lindlar’s catalyst

B) 1. KOEt; 2. HBr, Lindlar’s catalyst

C) 1. KOEt; 2. O3

D) 1. KOEt; 2. H3O+

E) 1. KOEt; 2. H2, Pt

Diff: 3

Learning Objective: Spectroscopy

108) Through a multistep synthesis, 2-methylpentane (C6H14) can be converted to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Which synthetic pathway would prepare such a compound from 2-methylpentane?

A) 1. NBS, hv; 2. KOtBu; 3. Br2

B) 1. NBS, hv; 2. KOtBu; 3. HBr, ROOR

C) 1. Br2, hv; 2. KOtBu; 3. HBr, H3O+

D) 1. NBS; 3. HBr, ROOR

E) 1. NBS, hv; 2. KOtBu; 3. ROOR

Diff: 3

Learning Objective: Spectroscopy

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Chapter 11 Synthesis

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