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Test Bank | Conjugated Pi Systems And Pericyclic – Ch.16

Organic Chemistry, 4e (Klein)

Chapter 16 Conjugated Pi Systems and Pericyclic Reactions

1) Dienes with π bonds separated by exactly one σ bond are classified as ________.

A) isolated

B) cumulated

C) skipped

D) conjugated

E) terminal

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

2) Dienes with adjacent π bonds are classified as ________.

A) isolated

B) cumulated

C) skipped

D) conjugated

E) terminal

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

3) Dienes with π bonds separated by two or more σ bonds are classified as ________.

A) isolated

B) cumulated

C) skipped

D) conjugated

E) terminal

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

4) Identify from the following compounds the isolated diene.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

5) Identify from the following compounds the conjugated diene.

An illustration depicts five compounds. The first compound has a SMILES string of C=C1CCC=CC1. The second compound has a SMILES string of CC1=CCCC=C1. The third compound has a SMILES string of CC1C=CCC=C1. The fourth compound has a SMILES string of CC1CCCC=C1. The fifth compound has a SMILES string of CC1=CCC=CC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

6) Identify from the following compounds those having conjugated double bonds.

A) II and V

B) II, IV, and V

C) I and III

D) II and IV

E) I, III, and IV

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

7) Identify from the following compounds those having isolated double bonds.

A) II and IV

B) III and V

C) I, III, and V

D) I and V

E) I and III

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

8) Classify the double bonds in the following compounds as cumulated, conjugated or isolated.

An illustration depicts two compounds. The first compound has a cyclopentane ring fused to a cyclohexane ring. The C 3-C 9, and C 7-C 8 are double bonded. The C 7 is also bonded to a methyl group. The second compound has a cyclohexane ring. C 1 is double bonded to a carbon atom, which is further single bonded to two methyl groups. There is a dot at the center of the double bond.

A) I = cumulated; II = conjugated

B) I = cumulated; II = isolated

C) I = conjugated; II = isolated

D) I = isolated; II = cumulated

E) I = conjugated; II = cumulated

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

9) Identify the cumulated diene from the following options.

A) 4-methyl-1,3-heptadiene

B) 3-methyl-1,5-heptadiene

C) 2-methyl-2,4-heptadiene

D) 4-methyl-1,4-heptadiene

E) 5-methyl-2,3-heptadiene

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

10) Identify the conjugated diene from the following options.

A) 4-methyl-1,3-heptadiene

B) 3-methyl-1,5-heptadiene

C) 2-methyl-2,5-heptadiene

D) 4-methyl-1,4-heptadiene

E) 5-methyl-2,3-heptadiene

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

11) Identify the isolated diene from the following options.

A) 4-methyl-1,3-heptadiene

B) 3-methyl-1,5-heptadiene

C) 2-methyl-2,4-heptadiene

D) 4-methyl-1,2-heptadiene

E) 5-methyl-2,3-heptadiene

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

12) Zingiberene, a terpene found in ginger, has the structure shown below. Classify the π bonds in zingiberene as conjugated, cumulated or isolated.

An illustration depicts a compound named Zingiberene with a SMILES string of CC1=CCC(C=C1)C(C)CCC=C(C)C. The double bond in the carbon chain is labeled Roman numeral 1. The two double bonds in the six membered ring are labeled Roman numeral 2 (between C 1-C 2) and Roman numeral 3 (between C 3-C 4).

A) I = cumulated; II = conjugated; III = cumulated

B) I = isolated; II = isolated; III = conjugated

C) I = conjugated; II = isolated; III = cumulated

D) I = isolated; II = conjugated; III = conjugated

E) I = cumulated; II = cumulated; III = isolated

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

13) Vitamin D3 has the structure shown below. Classify the π bonds in vitamin D3 as conjugated, cumulated or isolated.

$An illustration depicts the structure of Vitamin D 3 that has a SMILES string of C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C. The six-membered ring fused with a five membered ring is present in the structure of vitamin D 3. The double bond attached to this six membered ring is labeled Roman numeral 1. Another six membered ring is also present in the structure of vitamin D 3. The two double bonds bonded to this six membered ring are labeled roman numerals 2 (alternate to the first double bond) and 3, respectively.$

A) I = isolated; II = conjugated; III = conjugated

B) I = conjugated; II = conjugated; III = conjugated

C) I = isolated; II = isolated; III = isolated

D) I = isolated; II = cumulated; III = conjugated

E) I = cumulated; II = cumulated; III = cumulated

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

14) What is the IUPAC name for the following compound?

An illustration depicts a compound. The compound has a six-membered ring with a SMILES string of C1C=CCC=C1. One double bond is on the left and the other is on the right. The top center carbon is single bonded to a chlorine atom and also with a methyl group.

A) 1-chloro-1-methyl-2,5-cyclohexadiene

B) 3-chloro-3-methyl-1,4-cyclohexadiene

C) 6-chloro-6-methyl-1,4-cyclohexadiene

D) 2-chloro-2-methyl-1,3-cyclohexadiene

E) 5-chloro-5-methyl-1,3-cyclohexadiene

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

15) What is the IUPAC name for the following compound?

$An illustration depicts a compound with a SMILES string of C/C=C/C=C\C.$

A) (2Z,4E)-2,4-hexadiene

B) (2E,4Z)-1,4-dimethyl-1,3-butadiene

C) (2Z,4Z)-1,4-dimethyl-1,3-butadiene

D) (2Z,4Z)-2,4-hexadiene

E) (2E,4Z)-5-methyl-2,4-pentadiene

Diff: 3

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

16) What is the IUPAC name for the following compound?

An illustration depicts a compound which has a linear carbon chain of eight carbon atoms. From right to left, the C 2-C 3, C 4-C 5, and C 6-C 7 atoms are double bonded. The C 2, C 5, and C 6 atoms are each single bonded to a methyl group.

A) (2E,4Z,6E)-3,4,7,8-tetramethyl-2,4,6-heptatriene

B) (2Z,4E)-3,4,7-trimethyl-2,4,6-octatriene

C) (2E,4Z,6E)-2,5,6,7-tetramethyl-3,5,7-heptatriene

D) (2E,4Z)-2,5,6-trimethyl-3,5,7-octatriene

E) (4E,6E)-2,5,6-trimethyl-2,4,6-octatriene

Diff: 3

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

17) What is the IUPAC name for the following compound?

An illustration depicts a compound which has a five-membered ring. The C 1 of the five membered ring is single bonded to a methyl group. The C 1 and C 2 atoms are double bonded. The C 3 and C 4 atoms are double bonded. The C 4 is bonded to a carbon atom which is further bonded to two methyl groups.

A) 1-isopropyl-4-methyl-1,3-cyclopentadiene

B) 2-isopropyl-5-methyl-2,4-cyclopentadiene

C) 4-isopropyl-2-methyl-1,3-cyclopentadiene

D) 3-isopropyl-5-methyl-1,2-cyclopentadiene

E) 1-isopropyl-3-methyl-1,3-cyclopentadiene

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

18) Which of the following is the correct structure of (E)-2-methyl-1,3-pentadiene?

$An illustration depicts five compounds. The first compound labeled as Roman numeral one has a SMILES string of CC(=CC=C)C. The second compound labeled as Roman numeral two has a SMILES string of C/C=C/C(=C)C. The third compound labeled as Roman numeral three has a SMILES string of C/C=C(/C)\C=C. The fourth compound labeled as Roman numeral four has a SMILES string of C/C=C\C(=C)C. The fifth compound labeled as Roman numeral five has a SMILES string of C/C=C(/C)\C=C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

19) Which of the following is the correct structure of (Z)-2-methyl-2,4-hexadiene?

$An illustration depicts five compounds. The first compound labeled as Roman numeral one has a SMILES string of C/C=C/C=C(C)C. The second compound labeled as Roman numeral two has a six-carbon chain. C 2 is double bonded to C 3, which is single bonded to a methyl group. C 4 is double bonded to C 5. The third compound labeled as Roman numeral three has a SMILES string of C/C=C\C=C(C)C. The fourth compound labeled as Roman numeral four has a SMILES string of C/C=C/C(=C/C)/C. The fifth compound labeled as Roman numeral five has a linear carbon chain of four carbon atoms. The C 1 atom bonded to a methyl group is in upward direction. The C 1 and C 2 atoms are double bonded. The C 3 atom is bonded to a methyl group. The C 3 and C 4 atoms are double bonded.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

20) Which of the following is the correct structure of (1E,3Z)-1-methoxy-2-methyl-1,3-pentadiene?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

21) Identify the structure for (S,E)-3-tert-butyl-4-methyl-1,4-hexadiene.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

22) Predict the major product of the following reaction.

An illustration depicts a chemical reaction. The reactant has a linear carbon chain of six carbon atoms. C 2 is double bonded to C 3. The C 4 atom is bonded to a bromine atom, B r. The reactant reacts in the presence of potassium tert-butoxide, left parenthesis C H 3 right parenthesis 3 C O K. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

23) Predict the major product of the following reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C1CCC(C(C1)Br)Br. This reacts in the presence of potassium tert-butoxide, C H 3 inside parentheses 3 C O K. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

24) Classify the following compounds as having cumulated, conjugated or isolated double bonds.

An illustration depicts two compounds. The first compound labeled as Roman numeral one has a SMILES string of C=C1CCC(=C)CC1. The second compound labeled as Roman numeral two has a six membered cyclohexene ring. C 1 is bonded to a four-carbon chain, in which C 1 is single bonded to a methyl group and double bonded to C 2. C 3 is double bonded to C 4. C 2 of the ring is bonded to a methyl group.

A) I = cumulated; II = isolated

B) I = cumulated; II = conjugated

C) I = conjugated; II = isolated

D) I = isolated; II = conjugated

E) I = conjugated; II = cumulated

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

25) Predict the major product of the following reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C1CC=CC(C1)Cl. This reacts in the presence of potassium tert-butoxide, C H 3 inside parentheses 3 C O K. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

26) Identify the reagents necessary to carry out the following transformation.

An illustration depicts a chemical transformation. The reactant has a SMILES string of C1CCC=CC1. The product has a SMILES string of C1CC=CC=C1.

A) 1. Br2; 2. Mg; 3. H2O

B) 1. H2, Pd catalyst; 2. NBS, heat

C) 1. HBr; 2. (CH3)3COK

D) 1. MCPBA; 2. H3O+

E) 1. NBS, heat; 2. (CH3)3COK

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

27) Identify the reagents necessary to carry out the following transformation.

An illustration depicts a chemical transformation. The reactant has a SMILES string of C1CCC(CC1)O. The product has a SMILES string of C1CC=CC=C1.

A) 1. H2SO4, heat; 2. NBS, heat; 3. (CH3)3COK

B) 1. PBr3; 2. (CH3)3COK; 3. Br2/H2O

C) 1. 1 eq. H2, Pd/C; 2. BH3; 3. H2O2, NaOH

D) 1. SOCl2/pyridine; 2. Mg in ether; 3. H2O

E) 1. NBS, heat; 2. (CH3)3COK

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

28) Identify the reagents necessary to carry out the following transformation.

An illustration depicts a chemical transformation. The reactant has a SMILES string of C1CCCCC1. The product has a SMILES string of C1CC=CC=C1.

A) 1. H2, Pd/C

B) 1. PBr3; 2. (CH3)3COK

C) 1. Br2, hν; 2. (CH3)3COK; 3. NBS, heat; 4. (CH3)3COK

D) 1. SOCl2/pyridine; 2. Mg in ether; 3. H2O; 4. (CH3)3COK

E) 1. (CH3)3COK; 2. NBS, heat; 3. (CH3)3COK

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

29) Which of the following indicated C–C bonds is the shortest?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

30) Which of the following indicated C–C bonds is the longest?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

31) Which of the following dienes is most stable?

A) CH3CH=CHCH=CHCH3

B) CH3CH=CHCH2CH=CH2

C) CH2=CHCH2CH2CH=CH2

D) CH2=CHCH(CH3)CH=CH2

E) CH3CH=C=CHCH2CH3

Diff: 1

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

32) Which of the following dienes is least stable?

A) CH3CH=CHCH=CHCH3

B) CH3CH=CHCH2CH=CH2

C) CH2=CHCH2CH2CH=CH2

D) CH2=CHCH(CH3)CH=CH2

E) CH3CH=C=CHCH2CH3

Diff: 1

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

33) Which of the following dienes is least stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

34) Rank the following dienes in order of increasing stability (least to most).

A) I < III < II

B) III < II < I

C) II < III < I

D) II < I < III

E) III < I < II

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

35) Which one of the following dienes is most stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

36) Which one of the following dienes will have the lowest heat of hydrogenation?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

37) Which one of the following dienes is the most stable stereoisomer in its most stable conformation?

$An illustration depicts five dienes. The first diene is in s-trans position and has a SMILES string of C/C=C/C=C/C. The second diene is in s-trans position and has a SMILES string of C/C=C\C=C/C. The third diene is in s-cis position and has a SMILES string of C/C=C\C=C/C. The fourth diene is in s-cis position and has a SMILES string of C/C=C/C=C\C. The fifth diene is in s-cis position and has a SMILES string of C/C=C/C=C/C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

38) Rank the following dienes in order of decreasing heat of hydrogenation (highest to lowest).

A) III > I > II > IV

B) IV > II > III > I

C) II > III > I > IV

D) I > II > IV > III

E) IV > III > II > I

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

39) Rank the following dienes in order of decreasing heat of hydrogenation (highest to lowest).

A) III > I > II > IV

B) IV > III > II > I

C) II > III > I > IV

D) I > II > IV > III

E) IV > II > I > III

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

40) Both s-cis and s-trans conformers of 1,3-butadiene have a continuous conjugated π system. Which of the following statements is true about the s-cis conformer?

A) The s-cis conformer is lower in energy than the s-trans conformer

B) The s-cis conformer is higher in energy than the s-trans conformer

C) The s-cis conformer has equal energy as the s-trans conformer

D) The s-cis conformer cannot be converted into the s-trans conformer

E) The equilibrium favors the s-cis conformer

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

41) Which one of the following represents the lowest energy π-bonding molecular orbital of 1,3-butadiene?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

42) Which one of the following represents the highest energy π-antibonding molecular orbital of 1,3-butadiene?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

43) How many π -bonding molecular orbitals does 1,3-pentadiene have?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

44) How many electrons does the HOMO of 1,3-pentadiene have in its excited state?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

45) How many electrons does the HOMO of 2,4-hexadiene have in its ground state?

A) 1

B) 2

C) 3

D) 4

E) 0

Diff: 2

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

46) How many electrons does the LUMO of 2,4-hexadiene have in its ground state?

A) 1

B) 2

C) 3

D) 4

E) 0

Diff: 2

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

47) Which one of the following represents the HOMO of 1,3,5-hexatriene?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

48) Which one of the following represents the LUMO of 1,3,5-hexatriene?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.3 Explain the circumstances under which a π electron in the HOMO can absorb a photon of light, and describe what happens when that event occurs

49) Identify the major products possible from the following reaction?

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C=C. This reacts in the presence of hydrogen bromide, H B r. The question mark is present on the product side.

$An illustration depicts six possible products. The first product labeled as Roman numeral one has a SMILES string of C/C=C/C(C)Br. The second product labeled as Roman numeral two has a SMILES string of CC/C(=C/C)/Br. The third product labeled as Roman numeral three has a SMILES string of CCC(C=C)Br. The fourth product labeled as Roman numeral four has a SMILES string of BrCC\C=C\C. The fifth product labeled as Roman numeral five has a SMILES string of CC(CC=C)Br. The sixth product labeled as Roman numeral six has a SMILES string of C/C=C/C(C)Br.$

A) I and V

B) II and IV

C) III and IV

D) I, III and VI

E) II, IV and V

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

50) Which one of the following compounds is not a product of the reaction between 1,3-butadiene and HBr?

A) (S)-3-bromo-1-butene

B) (R)-3-bromo-1-butene

C) (E)-1-bromo-2-butene

D) (Z)-1-bromo-2-butene

E) (Z)-2-bromo-2-butene

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

51) Identify the products of the 1,2-addition for the following reaction.

A) I and III

B) II and IV

C) II and III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

52) Identify the products of the 1,2-addition for the following reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC(=C)C=1CCCCC=1. This reacts in the presence of hydrogen bromide, H B r. The question mark is present on the product side.

A) I and III

B) II and IV

C) II and III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

53) Identify the products of the 1,2-addition for the following reaction.

$An illustration depicts a chemical reaction. The reactant has a SMILES string of C\1=C\C=C/CC/1(C)C. This reacts in the presence of hydrogen bromide, H B r. The question mark is present on the product side.$

A) I and III

B) II and IV

C) II and III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

54) Identify the products of the 1,4-addition reaction of 1,3-hexadiene with Br2/CCl4.

A) I

B) II

C) III

D) I and III

E) II and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

55) Identify the products of the 1,2-addition for the following reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C1CC=C2CCCC=C2C1. This reacts in the presence of bromine, B r 2 and carbon tetrachloride, C C l 4. The question mark is present on the product side.

A) I

B) I and II

C) III

D) IV

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

56) A thermodynamically-controlled process describes a reaction that ________.

A) generates the most stable product

B) generates the product whose formation requires the smallest energy of activation

C) generates the product requiring the fewest steps

D) generates the product formed at the fastest rate

E) generates the product favored at low temperatures

Diff: 1

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

57) A kinetically-controlled process describes a reaction that ________.

A) generates the most stable product

B) generates the product whose formation requires the smallest energy of activation

C) generates the product requiring the fewest steps

D) generates the product formed at the slowest rate

E) generates the product favored at high temperatures

Diff: 1

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

58) The reaction of 1,3-butadiene with a hydrohalide at 0°C will undergo a ________ under ________ control.

A) 1,2-addition; kinetic

B) 1,4-addition; thermodynamic

C) 1,2-addition; thermodynamic

D) 1,3-addition; kinetic

E) 1,4-addition; kinetic

Diff: 1

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

59) The reaction of 1,3-butadiene with a hydrohalide at 40°C will undergo a ________ under ________ control.

A) 1,2-addition; kinetic

B) 1,4-addition; thermodynamic

C) 1,2-addition; thermodynamic

D) 1,3-addition; kinetic

E) 1,4-addition; kinetic

Diff: 1

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

60) Identify the major product(s) for the following reaction.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 2

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

61) Identify the major product(s) for the following reaction.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 2

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

62) Identify the structure for 1,2-addition product for the following reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC1=CC=C(CC1)C. This reacts in the presence of hydrogen bromide, H B r. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

63) Identify the expected major product(s) for the following reaction.

An illustration depicts an incomplete chemical reaction and five possible products along with their enantiomers. The reactant has a SMILES string of CC1=CCCC=C1C. This reacts with hydrogen bromide, H B r at 40 degree Celsius. A question mark is depicted on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

64) Identify the expected major product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

65) The polymerization of isoprene to produce synthetic rubber is a special case of

________.

A) 1,1-addition

B) 1,2-addition

C) 1,3-addition

D) 1,4-addition

E) 2,2-addition

Diff: 1

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

66) The addition of a(n) ________ bond improves the elasticity in synthetic rubber.

A) ionic

B) disulfide

C) pi

D) sigma

E) hydrogen

Diff: 1

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

67) Which of the following is true of pericyclic reactions?

A) they are concerted reactions

B) proceed via a cyclic transition state

C) no intermediates are formed

D) the polarity of the solvent generally does not impact the reaction rate

E) all of these

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

68) Identify the pericyclic reaction in which two pi bonds are broken and two sigma bonds are formed.

A) sigmatropic rearrangement

B) cycloaddition reaction

C) electrolytic reaction

D) Woodward-Fieser reaction

E) polymerization reaction

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

69) Identify the pericyclic reaction in which two sigma bonds are broken and two pi bonds are formed.

A) sigmatropic rearrangement

B) cycloaddition reaction

C) electrolytic reaction

D) this is not a pericyclic reaction

E) Woodward-Fieser reaction

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

70) Identify the pericyclic reaction in which one pi bond is broken and one sigma bond is formed.

A) sigmatropic rearrangement

B) cycloaddition reaction

C) electrolytic reaction

D) Woodward-Fieser reaction

E) polymerization reaction

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

71) Identify the pericyclic reaction in which no pi bonds are broken and no sigma bonds are formed.

A) sigmatropic rearrangement

B) cycloaddition reaction

C) electrolytic reaction

D) Woodward-Fieser reaction

E) polymerization reaction

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

72) What is the correct classification of the following pericyclic reaction?

An illustration depicts a pericyclic reaction. The reactant has a SMILES string of CC(C=C)C(C)C=C. This reacts in the presence of heat. The product has a SMILES string of C/C=C/CC/C=C/C.

A) electrophilic addition

B) sigmatropic rearrangement

C) cycloaddition

D) electrocyclic reaction

E) nucleophilic substitution

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

73) What is the correct classification of the following pericyclic reaction?

An illustration depicts a pericyclic reaction. The first compound has a six-membered ring in which C 1 and C 2 atoms are double bonded. The C 1 and C 2 atoms each is single bonded to a carbon atom which in turn is double bonded to a methyl group. The product has a SMILES string of C1CC=C2CCCCC2=C1.

A) electrophilic addition

B) sigmatropic rearrangement

C) cycloaddition

D) electrocyclic reaction

E) nucleophilic substitution

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

74) What is the correct classification of the following pericyclic reaction?

An illustration depicts a pericyclic reaction. The reactant have SMILES string of C=C1CCCCC1=C and C=C, respectively. The product has a SMILES string of C1CCC2=C(C1)CCCC2.

A) electrophilic addition

B) sigmatropic rearrangement

C) cycloaddition

D) electrocyclic reaction

E) nucleophilic substitution

Diff: 1

Learning Objective: 16.6 Identify three types of pericyclic reactions

75) Which statement is not true about the Diels-Alder reaction?

A) It is a [4+2] cycloaddition reaction.

B) The diene must be in the s-cis conformation to react.

C) Most Diels-Alder reactions are reversible.

D) It is a sigmatropic rearrangement.

E) Electron donating groups on the diene and electron withdrawing groups on the dienophile favor product formation.

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

76) The Diels Alder reaction is a concerted reaction. Define concerted.

A) A reaction where the product contains a cyclic ring.

B) A reaction where the diene must be in the s-cis conformation to react.

C) A reaction where all changes in bonding (bond making and bond breaking) occur simultaneously.

D) Another term for an endothermic reaction.

E) A reaction where both exo and endo products are formed.

Diff: 1

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

77) Which of the following dienes can undergo a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

78) Which of the following dienes cannot undergo a Diels-Alder reaction?

An illustration depicts four dienes compounds. The first compound labeled as Roman numeral one has a SMILES string of C1CCC2C=CC=CC2C1. The second compound labeled as Roman numeral two has a SMILES string of C1CC=C2CCCC=C2C1. The third compound labeled as Roman numeral three has a SMILES string of C=CC1=CCCCC1. The fourth compound labeled as Roman numeral four has a SMILES string of C=C1CCCC=C1.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

79) Which of the following dienophiles is least reactive in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

80) Which of the following dienophiles is most reactive in a Diels-Alder reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

81) The following diene does not undergo Diels Alder reaction because ________.

An illustration depicts a diene compound that has a six membered ring fused together. The C 3 and C 4 atoms are double bonded. The C 5 and C 10 atoms are double bonded.

A) it does not have an electron donating group

B) it does not have an electron withdrawing group

C) the bicyclic ring does not function as a diene

D) it cannot adopt the s-cis conformation

E) the double bonds are not in the same cyclic ring

Diff: 1

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

82) Identify the expected major product of the following Diels-Alder reaction.

An illustration depicts a Diels-alder reaction. The reactant has a SMILES string of C=CC=C and a SMILES string of CC(=O)C=C. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

83) Identify the expected major product of the following Diels-Alder reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

84) Identify the expected major product of the following Diels-Alder reaction.

An illustration depicts a Diels-alder reaction. The first reactant has a SMILES string of C1CC=CC=C1. The second reactant has a SMILES string of C(#CC#N)C#N. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

85) Identify the expected major product of the following Diels-Alder reaction.

$An illustration depicts a Diels-alder reaction. The reactant has a SMILES string of C=CC1=CCCCC1 and a SMILES string of C(=C\C(=O)O)\C(=O)O. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

86) Identify the expected major product of the following Diels-Alder reaction.

An illustration depicts a Diels-alder reaction. The reactant has a SMILES string of C=CC=C and a SMILES string of CCCCC=C. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

87) Identify the expected major product of the following Diels-Alder reaction.

An illustration depicts a Diels-alder reaction. The reactant has a SMILES string of C1C=CC=C1 and CC(=O)C(=C)Cl. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

88) Identify the expected major product of the following Diels-Alder reaction.

An illustration depicts a Diels-alder reaction. The reactants have SMILES string of C=CC=C labeled as, Excess and C1=CC(=O)C=CC1=O, respectively. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

89) Identify the expected major product of the following Diels-Alder reaction.

An illustration depicts a Diels-alder reaction. The reactant has a SMILES string of C1C=CC=C1 and C1=CC(=O)OC1=O. A plus sign is present in between the reactants. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

90) Compound A is one of the intermediate products in the synthesis of the corticoid hormone cortisone. Identify the structure of compound A.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

91) Identify the expected major products of the following Diels-Alder reaction.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

92) Identify the expected major products of the following intramolecular Diels-Alder reaction.

A) I and II

B) III

C) IV

D) V and VI

E) I, II, V and VI

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

93) The following Diels-Alder reaction product is an intermediate in the synthesis of estrone. Identify the structure of the products.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

94) The following Diels-Alder reaction product is an intermediate in the synthesis of cholesterol. Identify the structure of the product.

A) I and II

B) II and III

C) III and IV

D) I and III

E) II and IV

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

95) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

$An illustration depicts five pairs of compounds. The first pair labeled as Roman numeral one has SMILES string of C=C and C=C(C(=C)C(=O)O)C(=O)O separated by a plus sign in-between. The second pair labeled as Roman numeral two has SMILES strings of C=CC=C and C(=C\C(=O)O)\C(=O)O separated by a plus sign in-between. The third compound labeled as Roman numeral three has SMILES string of C/C=C\C and C(#CC(=O)O)C(=O)O separated by a plus sign in-between. The fourth compound labeled as Roman numeral four has SMILES string of C/C=C/C=C\C and C(=C\C(=O)O)\C(=O)O separated by a plus sign in-between. The fifth compound labeled as Roman numeral five has SMILES string of C/C=C/C=C/C and C(=C\C(=O)O)\C(=O)O separated by a plus sign in-between.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

96) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts a compound with a SMILES string of C1CC2CCC1C=C2.

$An illustration depicts five pairs of compounds. The first pair labeled as Roman numeral one has SMILES string of C=CC=C and C1CCC=CC1 separated by a plus sign in-between. The second pair labeled as Roman numeral two has SMILES string of C1CCC=CC1 and C/C=C\C separated by a plus sign in-between. The third pair labeled as Roman numeral three has SMILES string of CC1CCC(C=C1)C and C=C separated by a plus sign in-between. The fourth pair labeled as Roman numeral four has SMILES string of C1CC=CC=C1 and CC(=O)C=C separated by a plus sign in-between. The fifth pair labeled as Roman numeral five has SMILES string of C1CC=CC=C1 and C#C separated by a plus sign in-between.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

97) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts a compound with a SMILES string of CC(=O)C1CC2CCC1C=C2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

98) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts the Diels-Alder product.
The product has a bridged cyclohexene structure. C 5 is double bonded to C 6. C 1 and C 4 are connected through a two-carbon bridge. The C 2 and C 3 are each single bonded to C N and H.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

99) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts a Diels-Alder product.
The product has a six membered cyclohexene ring fused to a five membered cyclopentane ring. Both rings share two wedge bonded hydrogen atoms.

$An illustration depicts five pairs of dienes and dienophiles. The first pair has two compounds. The first compound has a SMILES string of C=CC=C. The second compound has a SMILES string of C1CC=CC1. The second pair has two compounds. The first compound has a SMILES string of C1CCC=CC1. The second compound has a SMILES string of C1C=CC=C1. The third pair has two compounds. The first compound has a SMILES string of C1CC=CC=C1. The second compound has a SMILES string of C1CC=CC1. The fourth pair has two compounds. The first compound has a SMILES string of C/C=C\C. The second compound has a SMILES string of C=C1CCCC1=C. The fifth pair has two compounds. The first compound has a SMILES string of C=CC=C. The second compound has a SMILES string of C1C=CC=C1.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

100) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts the Diels-Alder product.
The product has a cyclohexene ring fused to a cyclohexane ring. C 2 of the cyclohexene is double bonded to C 3. The C 1 is bonded to an oxygen atom which is then bonded to another carbon atom. This carbon atom is double bonded to an oxygen atom and single bonded to C 4 atom of the cyclohexene.

$An illustration depicts five pairs of dienes and dienophiles. First pair: The diene has a SMILES string of C1CC=CC=C1. The dienophile has a SMILES string of C1C=CCOC1=O. Second pair: The diene has a SMILES string of C=CC(=O)OC=C. The dienophile has a SMILES string of C1CCC=CC1. Third pair: The diene has a SMILES string of c1ccoc(=O)c1. The dienophile has a SMILES string of C1CCC=CC1. Fourth pair: The diene has a SMILES string of C/C=C\C=C/C. The dienophile has a SMILES string of C1C=CCOC1=O. Fifth pair: The diene has a SMILES string of C1CC=CC=C1. The dienophile has a linear carbon chain of five carbon atoms in which C 2 and C 3 are double bonded. The C 1 is bonded to an O H group while the C 5 is double bonded to an oxygen atom.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

101) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts a Diels-Alder product.
The product has a cyclohexene ring. C 1 and C 4 are connected through a bridged oxygen atom. C 2 is double bonded to C 3. The C 5 is bonded to a carbon atom which is then double bonded to an oxygen atom and single bonded to O C H 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

102) Classify the following compounds as having cumulated, conjugated or isolated double bonds.

A) I = isolated; II = conjugated

B) I = cumulated; II = isolated

C) I = conjugated; II = isolated

D) I = cumulated; II = conjugated

E) I = conjugated; II = cumulated

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

103) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts a compound with a SMILES string of C1CCC2=C3CCCCC3C4C(C2C1)C(=O)OC4=O.

$An illustration depicts five pairs of dienes and dienophiles. First pair: The diene has a SMILES string of C1CCC(=CC1)C2=CCCCC2. The dienophile has a SMILES string of C1=CC(=O)OC1=O. Second pair: The diene has a SMILES string of C1CCC(=C2CCCCC2)CC1. The dienophile has a SMILES string of C=C1C(=C)C(=O)OC1=O. Third pair: The diene has two six membered cyclohexane rings. The C 2 of the first ring is bonded to C 2 of the second ring. The C 1 of the first ring and C 1 of the second ring are each double bonded to a methylene group. The dienophile has a SMILES string of C1=CC(=O)OC1=O. Fourth pair: The diene has a SMILES string of C1CCC=CC1. The dienophile has a SMILES string of C=C1C(=C)C(=O)OC1=O. Fifth pair: The diene has a SMILES string of C1CCC2=C3CCCCC3OC2C1. The dienophile has a SMILES string of C(=C\C=O)\C=O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

104) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts the Diels hyphen Alder product.
The product has two six membered cyclohexane rings fused to a six membered cyclohexene ring. C 10 a and C 10 b are double bonded. The bottom right carbon of the cyclohexene is single bonded to N O 2.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

105) The following product shown in the box is formed by an intramolecular Diels-Alder reaction. Identify the structure of the starting compound.

An illustration depicts a compound with a SMILES string of C1CC2C(CCC2=O)C=C1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

106) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts the Diels-Alder product.
The product has two five membered cyclopentane rings fused to a six membered cyclohexene ring. From right to left, C 8 a and C 8 b are double bonded. The top right carbon of the cyclohexene ring is single bonded to a carbon atom which is then double bonded to an oxygen atom and single bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

107) Identify the diene and dienophile expected to produce the Diels-Alder product shown in the box below.

An illustration depicts a Diels hyphen Alder product.
The product has a cyclohexadiene ring. C 1 and C 4 are bonded to a common oxygen atom. C 2 is double bonded to C 3. C 5 is double bonded to C 6. The C 3 is single bonded to C N.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

108) Identify the Molecular Orbitals that react to form cyclohexene in a Diels-Alder reaction.

A) HOMO of 1,3-butadiene and LUMO of ethylene

B) LUMO of 1,3-butadiene and LUMO of ethylene

C) HOMO of 1,3-butadiene and HOMO of ethylene

D) LUMO of 1,3-butadiene and LUMO of 1,3-butadiene

E) HOMO of 1,3-butadiene and HOMO of 1,3-butadiene

Diff: 2

Learning Objective: 16.8 Describe the Diels-Alder and other cycloaddition reactions in terms of molecular orbitals

109) Classify the following compounds as having cumulated, conjugated or isolated double bonds.

An illustration depicts two compounds. The first compound has a SMILES string of CCC=C=CC. The second compound has a cyclohexene ring in which C 1 is double bonded to a methylene group and C 4 is single bonded to a methyl group.

A) I = isolated; II = conjugated

B) I = cumulated; II = conjugated

C) I = conjugated; II = isolated

D) I = cumulated; II = isolated

E) I = conjugated; II = cumulated

Diff: 1

Learning Objective: 16.1 Identify cumulated, conjugated, and isolated dienes.

110) Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC/C=C/C=C/CC. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) disrotatory; cis-3,4-diethylcyclobutene

B) conrotatory; cis-3,4-diethylcyclobutene

C) disrotatory; trans-3,4-diethylcyclobutene

D) conrotatory; trans-3,4-diethylcyclobutene

E) disrotatory; 3,3-diethylcyclobutene

Diff: 3

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

111) Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC/C=C/C=C/CC. This reacts in the presence of sunlight, h v. The question mark is present on the product side.

A) disrotatory; cis-3,4-diethylcyclobutene

B) conrotatory; cis-3,4-diethylcyclobutene

C) disrotatory; trans-3,4-diethylcyclobutene

D) conrotatory; trans -3,4-diethylcyclobutene

E) conrotatory; 3,3-diethylcyclobutene

Diff: 3

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

112) Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

An illustration depicts a chemical reaction. The reactant reads, 3 E, 5 Z, 7 E inside parentheses-3, 5, 7-decatriene. It reacts in the presence of sunlight, h nu. The question mark is present on the product side.

A) disrotatory; cis-5,6-diethyl-1,3-cyclohexadiene

B) conrotatory; cis-5,6-diethyl-1,3-cyclohexadiene

C) disrotatory; trans-5,6-diethyl-1,3-cyclohexadiene

D) conrotatory; trans -5,6-diethyl-1,3-cyclohexadiene

E) disrotatory; 5,5-diethyl-1,3-cyclohexadiene

Diff: 3

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

113) Which of the following best describes the stereochemistry of ring closure and the product for the following reaction?

An illustration depicts a chemical reaction. The reactant reads, 3 E, 5 Z, 7 E inside parentheses-3, 5, 7-decatriene. It reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) disrotatory; cis-5,6-diethyl-1,3-cyclohexadiene

B) conrotatory; cis-5,6-diethyl-1,3-cyclohexadiene

C) disrotatory; trans-5,6-diethyl-1,3-cyclohexadiene

D) conrotatory; trans -5,6-diethyl-1,3-cyclohexadiene

E) conrotatory; 5,5-diethyl-1,3-cyclohexadiene

Diff: 3

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

114) Identify the expected major product of the following electrocyclic reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC(=CC=C(C)C)C. This reacts in the presence of sunlight, h v. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

115) Identify the expected major product of the following electrocyclic reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

116) Identify the expected major product of the following electrocyclic reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C(=C/C)/C. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

117) Identify the expected product of the following Claisen rearrangement.

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC(C=C)Oc1ccccc1.This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

$An illustration depicts five compounds. The first compound labeled as I has a SMILES string of Oc1ccccc1C(\C=C)C. The second compound labeled as II has a SMILES string of CC(=C)Cc1ccccc1O. The third compound labeled as III has a SMILES string of Oc1ccccc1/C(=C/C)C. The fourth compound labeled as IV has a SMILES string of C/C=C/Cc1ccccc1O. The fifth compound labeled as V has a SMILES string of Oc1ccccc1\C=C(/C)C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

118) Identify the expected major product of the following Cope rearrangement.

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC(C)(CC=C)C=C. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

$An illustration depicts five compounds. The first compound labeled as I has a SMILES string of C/C=C\CC/C=C\C. The second compound labeled as II has a SMILES string of CC(=C)CCC(=C)C. The third compound labeled as III has a SMILES string of CC(=CCCC=C)C. The fourth compound labeled as IV has a SMILES string of CC(C=C)C(C)C=C. The fifth compound labeled as V has a SMILES string of C/C=C/CC/C=C/C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

119) Identify the expected product of the following Claisen rearrangement.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C=CC1(CC2CC1C=C2)O. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

120) Identify the expected product of the following Claisen rearrangement.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/COc1ccccc1. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

$An illustration depicts five products. The first product has a SMILES string of C/C=C/Cc1ccccc1O. The second product has a benzene ring in which C 1 is bonded to an O H group. The C 2 is bonded to a carbon atom which is then single bonded to an ethyl group and double bonded to a methylene group. The third product has a SMILES string of CC/C=C/c1ccccc1O. The fourth product has a SMILES string of Oc1ccccc1C(\C=C)C. The fifth product has a SMILES string of Oc1ccccc1/C(=C/C)C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

121) Identify the expected major product of the following Cope rearrangement.

An illustration depicts a chemical reaction involved in the Cope rearrangement. The reactant has two five membered rings in which C 2 of both the rings are bonded together. The C 1 of both the rings are each double bonded to a methylene group. A forward arrow with a delta symbol above it is present. A question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

122) Identify the reagents necessary to carry out the following transformation.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C1CCC(CC1)O. The product has a SMILES string of C1CC=CC=C1.

A) 1. H2SO4, heat; 2. HBr; 3. (CH3)3COK

B) 1. TsCl, pyr; 2. (CH3)3COK; 3. Br2; 4. (CH3)3COK

C) 1. 1 eq. H2, Pd/C; 2. BH3; 3. H2O2, NaOH

D) 1. SOCl2/pyridine; 2. Mg in ether; 3. H2O

E) 1. NBS, heat; 2. (CH3)3COK

Diff: 3

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

123) Identify the expected product labeled B in the following reaction sequence.

An illustration depicts a chemical reaction. The reactant has a SMILES string of c1ccc(cc1)O. This reacts in the presence of sodium hydroxide, N a O H and a reagent with a SMILES string of C=CCBr. The intermediate is labeled as A. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The product is labeled as B.

$An illustration depicts five compounds. The first compound labeled as I has a SMILES string of C/C=C/c1ccccc1O. The second compound labeled as II has a SMILES string of C/C=C\Oc1ccccc1. The third compound labeled as III has a SMILES string of Oc1ccccc1\C(=C)C. The fourth compound labeled as IV has a SMILES string of C=CCOc1ccccc1. The fifth compound labeled as V has a SMILES string of C=CCc1ccccc1O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

124) Which of the following best describes a Cope rearrangement?

A) [2,2] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms

B) [2,2] sigmatropic rearrangement with heteroatoms

C) [3,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms

D) [2,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms

E) [2,3] sigmatropic rearrangement with heteroatoms

Diff: 1

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

125) Which of the following best describes a Claisen rearrangement?

A) [2,2] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms

B) [2,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms

C) [2,3] sigmatropic rearrangement with heteroatoms

D) [3,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms

E) [3,3] sigmatropic rearrangement with heteroatoms

Diff: 1

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

126) Absorption of UV-visible radiation by a molecule results in ________ transitions.

A) electronic

B) nuclear

C) rotational

D) vibrational

E) atomic

Diff: 1

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

127) Which is the most energetically favorable UV transition for 1,3-butadiene?

A) n → σ*

B) n → π*

C) π2 → π3*

D) σ → σ*

E) π1 → π4*

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

128) Which of the following is primarily suited to the study of conjugation in organic compounds?

A) IR spectroscopy

B) NMR spectroscopy

C) Mass spectroscopy

D) UV-Vis spectroscopy

E) Raman spectroscopy

Diff: 1

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

129) Which of the following symbols is used to represent the molar absorptivity of a given compound in the UV-Vis region?

A) λ

B) ε

C) ν

D) γ

E) α

Diff: 1

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

130) Which of the following compounds has the longest λmax?

An illustration depicts five compounds. The first compound labeled as I has a SMILES string of CCC/C=C/C=C. The second compound labeled as II has a SMILES string of CCC/C=C/CC. The third compound labeled as III has a SMILES string of C/C=C/C/C=C/C. The fourth compound labeled as IV has a SMILES string of C/C=C/C=C/C=C. The fifth compound labeled as V has a SMILES string of CC(=CC(=C)C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

131) Which of the following compounds has the shortest λmax?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

132) Which of the following compounds has the longest λmax?

A) (E)-2-pentene

B) (Z)-2-pentene

C) 1-pentene

D) 1,3-hexadiene

E) 1,3,5-hexatriene

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

133) Which of the following compounds has the longest λmax?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

134) Which of the following compounds has the longest λmax?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

135) Using the Woodward-Fieser rules identify the best estimate for the λmax of the following compound.

An illustration depicts a compound which has two six membered cyclohexene rings fused together. From right to left, the C 1, C 2, and C 9 atoms are each single bonded to a methyl group.

A) 232 nm

B) 237 nm

C) 217 nm

D) 222 nm

E) 242 nm

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

136) Using the Woodward-Fieser rules identify the best estimate for the λmax of the following compound.

An illustration depicts a compound with a linear carbon chain of nine carbon atoms. C 2 is double bonded to C 3, C 4 is double bonded to C 5, and C 6 is double bonded to C 7. The C 3, C 4, C 7, and C 8 are each single bonded to a methyl group.

A) 247 nm

B) 262 nm

C) 267 nm

D) 272 nm

E) 277 nm

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

137) Using the Woodward-Fieser rules identify the best estimate for the λmax of the following compound.

An illustration depicts the compound with a SMILES string of CC1=CCC(C=C1)C(C)CCC=C(C)C.

A) 232 nm

B) 256 nm

C) 267 nm

D) 271 nm

E) 286 nm

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

138) A compound that absorbs yellow light would be expected to have which of the following colors?

A) orange

B) green

C) red

D) blue

E) violet

Diff: 2

Learning Objective: 16.12 Identify the origin of color for organic compounds

139) A compound that absorbs blue light would be expected to have which of the following colors?

A) orange

B) green

C) red

D) blue

E) yellow

Diff: 2

Learning Objective: 16.12 Identify the origin of color for organic compounds

140) Identify the type(s) of light-sensitive cells that function as photoreceptors.

A) rods

B) cones

C) disks

D) A and B

E) B and C

Diff: 1

Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision

141) Identify the light-sensitive compound in rods.

A) rhodopsin

B) cis-retinal

C) lycopene

D) trans-retinal

E) vitamin A

Diff: 1

Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision

142) Which of the following dienes is most stable?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

143) Which one of the following dienes is the least stable stereoisomer in its most stable conformation?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

144) Which one of the following dienes is the most stable stereoisomer in its least stable conformation?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

145) Which one of the following dienes is the least stable stereoisomer in its least stable conformation?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.2 Compare the stability of conjugated and isolated dienes, and identify the s-cis and s-trans conformations of conjugated dienes

146) Which one of the following compounds is not an expected product of the reaction between 1,3-butadiene and HBr?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

147) Identify the products of the 1,4-addition for the following reaction.

A) I and III

B) II and IV

C) II and III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

148) Identify the products of the 1,4-addition for the following reaction.

A) I and III

B) I and IV

C) II and III

D) II and IV

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

149) Identify the products of the 1,4-addition for the following reaction.

$An illustration depicts an incomplete chemical reaction and four possible products along with their enantiomers. The reactant has a SMILES string of C\1=C\C=C/CC/1(C)C. This reacts with hydrogen bromide, H B r. A question mark is depicted on the product side.$

A) I and III

B) II and IV

C) II and III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

150) Identify the products of the 1,2-addition reaction of 1,3-hexadiene with Br2/CCl4.

A) I

B) II

C) II and III

D) III

E) I and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

151) Identify the products of the 1,4-addition for the following reaction.

A) I

B) I and II

C) I and IV

D) IV

E) III and IV

Diff: 2

Learning Objective: 16.4 Identify the 1,2- and 1,4-adducts for addition of HX across a diene

152) Which of the following provides the best explanation for why the 1,2-addition product of the following reaction is favored?

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC1=CC=C(CC1)C. This reacts in the presence of hydrogen bromide, H B r and forty degrees Celsius. The question mark is present on the product side.

A) This reaction is under thermodynamic control, which favors the formation of the more stable trisubstituted double bond.

B) The reaction is under kinetic control which always gives the 1,2-addition product.

C) The reaction is under thermodynamic control which always gives the 1,2-addition product.

D) The 1,4-adduct is more stable and these conditions favor the less substituted alkene.

E) The 1,2-adduct is less stable and thus is formed faster under the reaction conditions.

Diff: 3

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

153) Identify the structure of the expected product for the following reaction under thermodynamic control.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.5 Compare and contrast addition reactions that are under kinetic control with those under thermodynamic control

154) Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

An illustration depicts a chemical reaction. The reactant has a SMILES string of CC1=CCCC=C1C. This reacts in the presence of hydrogen bromide, H B r and zero degree Celsius. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

155) Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

$An illustration depicts five diene and dienophile combinations. In the first combination, the diene has a SMILES string of C=C. The dienophile has a linear carbon chain of six carbon atoms in which C 2 C 3, and C 4 C 5 are double bonded. The C 3 is also bonded to a carbon atom which is then double bonded to an oxygen atom and single bonded to an O H group. The C 4 is also bonded to a carbon atom which is then double bonded to an oxygen atom and single bonded to an O H group. In the second combination, the diene has a SMILES string of CC(=C)C(=C)C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O. In the third combination, the diene has a SMILES string of CC/C=C\CC and the dienophile has a SMILES string of C(#CC(=O)O)C(=O)O. In the fourth combination, the diene has a SMILES string of C/C=C/C=C\C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O. In the fifth combination, the diene has a SMILES string of C/C=C/C=C/C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

156) Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

157) Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

$An illustration depicts five diene and dienophile combinations. In the first combination, the diene has a SMILES string of C/C=C/C=C/C and the dienophile has a SMILES string of C(=C/C(=O)O)\C(=O)O. In the second combination, the diene has a SMILES string of C/C=C\C=C/C and the dienophile has a SMILES string of C(=C/C(=O)O)\C(=O)O. In the third combination, the diene has a SMILES string of C/C=C/C=C\C and the dienophile has a SMILES string of C(=C/C(=O)O)\C(=O)O. In the fourth combination, the diene has a SMILES string of C/C=C/C=C\C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O. In the fifth combination, the diene has a SMILES string of C/C=C/C=C/C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

158) Identify the diene and dienophile expected to produce as one of the Diels-Alder products the compound shown in the box below.

$An illustration depicts five diene and dienophile combinations. In the first combination, the diene has a SMILES string of C/C=C/C=C/C and the dienophile has a SMILES string of C(=C/C(=O)O)\C(=O)O. In the second combination, the diene has a SMILES string of C/C=C\C=C/C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O. In the third combination, the diene has a SMILES string of C/C=C/C=C\C and the dienophile has a SMILES string of C(=C/C(=O)O)\C(=O)O. In the fourth combination, the diene has a SMILES string of C/C=C/C=C\C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O. In the fifth combination, the diene has a SMILES string of C/C=C/C=C/C and the dienophile has a SMILES string of C(=C\C(=O)O)\C(=O)O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

159) The following product shown in the box is formed by an intramolecular Diels-Alder reaction. Identify the structure of the starting compound.

An illustration depicts a product in a box.
The product has a six membered ring fused to a five membered ring. From right to left, the C 3 and C 9 atoms are dashed bonded. The C 4 and C 5 atoms are double bonded. The C 7 atom is wedged bonded to a methyl group. The C 1 and C 8 atoms are wedged bonded. An oxygen atom is double bonded to the C 1 atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 16.7 Predict the product of a Diels-Alder reaction

160) Identify the expected major product of the following electrocyclic reaction.

$An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C=C\C. This reacts in the presence of sunlight, h v. The question mark is present on the product side.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

161) Identify the expected major product of the following electrocyclic reaction.

$An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C=C\C. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

162) Identify the expected major product of the following electrocyclic reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C=C/C. This reacts in the presence of heat which is represented using a delta symbol above the forward arrow. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

163) Identify the expected major product of the following electrocyclic reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C=C/C. This reacts in the presence of sunlight, h v. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

164) Identify the expected major product of the following electrocyclic reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C(=C/C)/C. This reacts in the presence of sunlight, h v. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

165) Identify the expected major product of the following electrocyclic reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

166) Identify the expected major product of the following electrocyclic reaction.

An illustration depicts a chemical reaction. The reactant has a SMILES string of C/C=C/C(=C(C)C)C. This reacts in the presence of sunlight, h v. The question mark is present on the product side.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.9 Predict the products of an electrocyclic reaction, either under thermal conditions or photochemical conditions

167) Identify the expected product labeled A in the following reaction sequence.

$An illustration depicts five compounds. The first compound has a SMILES string of C/C=C/c1ccccc1O. The second compound has a SMILES string of C/C=C\Oc1ccccc1. The third compound has a SMILES string of Oc1ccccc1\C(=C)C. The fourth compound has a SMILES string of C=CCOc1ccccc1. The fifth compound has a SMILES string of C=CCc1ccccc1O.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.10 Describe the defining features of a sigmatropic rearrangement, and compare the Cope and Claisen rearrangements

168) Which of the following compounds has the shortest λmax?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

169) Which of the following compounds has the shortest λmax?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 16.11 Describe the relationship between λmax and the extent of conjugation, and use Woodward-Fieser rules to predict the λmax of simple compounds

170) Lack of what compound is responsible for the condition known as night blindness?

A) rhodopsin

B) cis-retinal

C) lycopene

D) trans-retinal

E) vitamin A

Diff: 1

Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision

171) A diet rich in what compound can help prevent the condition known as night blindness and improve vision?

A) lycopene

B) cis-retinal

C) trans-retinal

D) β-carotene

E) vitamin A

Diff: 1

Learning Objective: 16.13 Discuss the chemical change that occurs in the rods of the eye that stimulate nerve impulses that lead to vision

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Chapter 16 Conjugated Pi Systems And Pericyclic Reactions

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David R. Klein

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