Okuyama & Maskill: Organic Chemistry

Chapter 21: Multiple Choice Questions

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You have answered 8 out of 20 questions correctly.
Your percentage score is 40%.

Question 1

Which of the following dienophiles is the most reactive with buta-1,3-diene?

Your answer:

c)

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Compound (c) is the dienophile with the best combination of low steric hindrance and a low-energy LUMO (which is caused by the electron-
withdrawing anhydride residue); see pp. 471-2.

Question 2

Which of the following dienes cannot undergo Diels-Alder reactions?

Your answer:

a)

Correct answer:

d)

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A diene has to be able to assume an s-cis conformation in order to undergo Diels-Alder reactions, and (d) has a constrained s-trans
structure.

Question 3

Which of adducts (a)-(d) is the main product of the following Diels-Alder reaction?

Your answer:
 b)

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The relative configurations of the diene and dienophile are preserved in the concerted syn addition of a Diels-Alder reaction. For the
stereochemistry of Diels-Alder reactions, see pp. 471-4.

Question 4

Which of the following is the main product in the ozonolysis of 1,4-dimethylcyclohexene followed by a reductive workup with Zn and ethanoic
acid?

Your answer:

c)

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The products of ozonolysis followed by a reductive workup are aldehyde(s) and/or ketone(s). Note the position of the methyl substituent in
the ring-opened product. For ozonolysis of alkenes, see pp. 476-7.

Question 5

Which of the following is the main product in the ozonolysis of 1,5-dimethylcyclohexene followed by a workup with aqueous H2O2?

Your answer:

b)

Correct answer:

c)

Feedback:

The products of ozonolysis followed by an oxidative workup are carboxylic acid(s) and/or ketone(s). Note that the position of the methyl
substituent in the ring-opened product. For ozonolysis of alkenes, see pp. 476-7.

Question 6

Which of phenols (a)-(d) is the main product of the following thermal rearrangement?

 
 Your answer:

b)

Correct answer:

d)

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The reaction is a Claisen rearrangement which is a type of [3,3] sigmatropic rearrangement; see pp. 483-4.

Question 7

Which of unsaturated aldehydes (a)-(d) is the sigmatropic rearrangement product obtained by heating the following ether?

Your answer:

c)

Correct answer:

b)

Feedback:

The reaction is an aliphatic Claisen rearrangement which is a type of [3,3] sigmatropic rearrangement; see pp. 483-4.

Question 8

Which of the following reactions is not thermally allowed?

Your answer:

c)

Correct answer:

a)

Feedback:
 For some orbital symmetry controlled reactions, see pp. 478-5. Reaction (a) is a [2+2] cycloaddition, (b) a [3,3] sigmatropic rearrangement,
(c) an electrocyclic reaction, and (d) an ene reaction.

Question 9

Which of the following reactions is classified as an ene reaction?

Your answer:

c)

Correct answer:

d)

Feedback:

Reactions (a) and (b) are both [3,3] sigmatropic rearrangements, (c) an electrocyclic reaction, and (d) an ene reaction.

Question 10

Which of the following reactions is classified as an electrocyclic reaction?

Your answer:

c)

Feedback:

Reactions (a) and (b) are both [3,3] sigmatropic rearrangements, (c) an electrocyclic reaction, and (d) an ene reaction.

Question 11

Which of the following dienophiles is the most reactive in normal Diels-Alder reactions?

Your answer:

b)

Correct answer:

a)

Feedback:

The dienophile with the most electron-withdrawing substituent (with the lowest LUMO) is the most reactive; see pp. 471-2.

Question 12

Which of the following dienophiles is the least reactive in normal Diels-Alder reactions?

Your answer:
 b)

Feedback:

The dienophile with an electron-donating substituent (with the least low LUMO) is least reactive; see pp. 471-2.

Question 13

Which of adducts (a)-(d) is the main kinetic product of the following Diels-Alder reaction?

Your answer:

a)

Correct answer:

c)

Feedback:

Consider first the regioselectivity in this cycloaddition of an unsymmetrical diene and an unsymmetrical dienophile (see pp. 474-5); endo
selectivity then leads to the kinetically favoured adduct (see pp. 472-3).

Question 14

Which of the following is the main product in the ozonolysis of 1,3-dimethylcyclohexene followed by a workup with Zn and ethanoic acid?

Your answer:

c)

Correct answer:

d)

Feedback:

The products of ozonolysis followed by a reductive workup are aldehyde(s) and/or ketone(s). Note the position of the methyl substituent in
the ring-opened product. For ozonolysis of alkenes, see pp. 476-7.
Question 15

Which of the following is impossible as a resonance form of ozone?

Your answer:

c)

Feedback:

The central oxygen of (c) has four covalent bonds and a lone pair, i.e. 10 valence electrons, which is not possible.

Question 16

Which side-chain carbon makes a new bond to the benzene ring upon Claisen rearrangement of the following allylic phenyl ether?

Your answer:

b) C2

Correct answer:

c) C3

Feedback:

For the Claisen rearrangement, see p. 484.

Question 17

The following involves two pericyclic reactions. Which combination indicates correctly the types of reaction involved?

Your answer:

c) [4+2] cycloaddition + [4+1] cycloreversion

Correct answer:

d) [4+2] cycloaddition + cheletropic reaction

Feedback:

Carbon monoxide is lost from the intermediate adduct:

 
Question 18

Which of compounds (a)-(d) is the likely intermediate of the following transformation involving two electrocyclic reactions (ring opening and ring
closure)?

Your answer:

b)

Feedback:

For electrocyclic reactions, see pp. 481-2.

Question 19

Which of the following reactions is classified as a sigmatropic rearrangement?

Your answer:

c)

Correct answer:

a)

Feedback:

Reactions (b)-(d) are an electrocyclic reaction, an ene reaction, and a cheletropic reaction, respectively.

Question 20

Which of the following is classified as an electrocyclic reaction?

Your answer:

b)

Feedback:

The reaction types are given in the feedback to question 9.

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