Question 1

Which of the following compounds will undergo an $$S_N2$$ reaction fastest with NaI in acetone?

Accepted Answer

1-chloropentane

Question 2

Arrange the following carbocations in decreasing order of stability: (1) benzyl, (2) allyl, (3) tertiary, (4) secondary, (5) primary.

Accepted Answer

1 \u003e 2 \u003e 3 \u003e 4 \u003e 5

Question 3

Which of the following is the least nucleophilic species in polar aprotic solvents?

Accepted Answer

$$BF_4$$^-$$

Question 4

Which of the following is the strongest acid according to the provided acid strength table?

Accepted Answer

$$HClO_4$$

Question 5

A student mixes 2-bromopentane with NaCN in DMSO. What is the major product?

Accepted Answer

1-cyanopentane

Question 6

Which of the following solvents is most likely to favor an $$S_N2$$ reaction mechanism?

Accepted Answer

Acetone

Question 7

Which of the following is the best leaving group for nucleophilic substitution?

Accepted Answer

$$Cl^-$$

Question 8

Using Zaitsev's rule, which of the following alkenes is the most stable?

Accepted Answer

cyclohexene

Question 9

Which of the following alkyl halides is most likely to undergo rearrangement in an $$S_N1$$ reaction?

Accepted Answer

2-chloro-3,3-dimethylpentane

Question 10

What is the product of the following reaction: 2-methylpropene + HBr?

Accepted Answer

2-bromo-2-methylpropane

Question 11

Which of the following is a polar aprotic solvent?

Accepted Answer

Acetone

Question 12

Which of the following statements about nucleophilicity is correct?

Accepted Answer

Nucleophilicity increases with decreasing electronegativity.

Question 13

Which of the following is the correct order of leaving group ability?

Accepted Answer

$$I^- \u003e Br^- \u003e Cl^- \u003e F^-$$

Question 14

A reaction of cyclohexene with $$Br_2 in $$THF produces which major product?

Accepted Answer

trans-1,2-dibromocyclohexane

Question 15

Which of the following is the correct mechanism for the acid-catalyzed hydration of cyclopentene?

Accepted Answer

Formation of carbocation, nucleophilic attack by water, deprotonation

Question 16

Which of the following is the correct order of acid strength (from strongest to weakest) for the following acids: $$HClO_4$$, $$H_2SO_4$$, $$CH_3COOH$$, $$H_2O$$?

Accepted Answer

$$HClO_4$$ \u003e H_2SO_4 \u003e CH_3COOH \u003e H_2O$$

Question 17

Which of the following reactions will produce a racemic mixture?

Accepted Answer

Reaction of 2-bromobutane with NaCN in MeOH

Question 18

Which of the following is the correct product for the reaction of 1-bromopentane with NaOH in water?

Accepted Answer

1-pentanol

Question 19

Which of the following is the correct order of nucleophilicity in polar aprotic solvents: $$F^-$$, $$Cl^-$$, $$Br^-$$, $$I^-$$?

Accepted Answer

$$F^- \u003e Cl^- \u003e Br^- \u003e I^-$$

Organic Chemistry: Mechanisms, Reactivity, and Key Concepts Study Guide

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