Question 1

Which of the following alkyl halides is classified as a tertiary (3°) halide?

Accepted Answer

2-bromo-2-methylpropane

Question 2

Which factor most strongly favors an SN2 reaction over an SN1 reaction?

Accepted Answer

A strong nucleophile and a primary alkyl halide

Question 3

What is the major product when 2-bromobutane reacts with NaOH in ethanol under SN2 conditions?

Accepted Answer

2-butanol

Question 4

Which of the following statements about E2 elimination reactions is correct?

Accepted Answer

E2 reactions are stereospecific and require anti-coplanar arrangement of the leaving group and hydrogen

Question 5

Given the following reaction: $\mathrm{CH_3CH_2Br}$ + $\mathrm{NaOH}$ (aqueous), what is the expected stereochemical outcome?

Accepted Answer

Inversion of configuration at the carbon

Question 6

Which of the following best describes the Markovnikov addition of HBr to 2-methylpropene?

Accepted Answer

Br adds to the more substituted carbon

Question 7

Which of the following alkene isomers is more stable?

Accepted Answer

trans-2-butene

Question 8

A student is asked to predict the product of the following reaction: $\mathrm{CH_3CH_2CH_2Br}$ + $\mathrm{KOH}$ (ethanol, heat). Which mechanism is most likely and what is the major product?

Accepted Answer

E2, propene

Question 9

Which of the following statements about carbocation rearrangements is true?

Accepted Answer

Carbocation rearrangements can occur during SN1 and E1 reactions

Question 10

Which of the following is the best nucleophile for an SN2 reaction in a polar aprotic solvent?

Accepted Answer

$\mathrm{CH_3O^-}$

Question 11

When predicting the product of an E2 reaction using a Newman projection, which arrangement of the leaving group and hydrogen is required?

Accepted Answer

Anti-coplanar

Question 12

Which of the following reagents will result in anti-Markovnikov addition of H and OH to an alkene?

Accepted Answer

$\mathrm{BH_3}$ / $\mathrm{THF}$ followed by $\mathrm{H_2O_2}$ / $\mathrm{OH^-}$

Question 13

Which of the following best describes the stereochemical outcome of an E2 elimination of 2-bromobutane?

Accepted Answer

Formation of both cis- and trans-2-butene, with trans favored

Question 14

Which of the following is a correct IUPAC name for the alkene with the structure $\mathrm{CH_2=CHCH_2CH_3}$?

Accepted Answer

1-butene

Question 15

Which of the following statements about SN1 reactions is correct?

Accepted Answer

SN1 reactions produce a racemic mixture due to planar carbocation intermediate

Question 16

Which of the following is the best combination of substrate and reagent to achieve an E2 elimination?

Accepted Answer

Secondary alkyl halide and strong base

Question 17

Which of the following is a correct statement about the product of ozonolysis of 2-butene?

Accepted Answer

The product is two molecules of ethanal ($\mathrm{CH_3CHO}$)

Question 18

Which of the following is a correct statement about the effect of solvent on SN1 and SN2 reactions?

Accepted Answer

Polar protic solvents favor SN1 reactions

Question 19

A student is asked to predict the product of the following multistep reaction: 1-bromopropane is treated with NaOH (aq), then the resulting product is treated with HBr. What is the final product?

Accepted Answer

1-bromopropane

Question 20

Which of the following is the correct order of reactivity for alkyl halides in SN2 reactions?

Accepted Answer

Primary > Secondary > Tertiary

Substitution, Elimination, and Addition Reactions: Study Guide for Organic Chemistry

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