Question 1

Which reagent would you use for the mild oxidation of a primary alcohol to an aldehyde?

Accepted Answer

PCC

Question 2

In the substitution reaction shown, what happens to the hydrogen atom on the benzene ring?

Accepted Answer

It is replaced by the incoming group

Question 3

Which of the following alkyl halides would react slowest with methanol in an SN2 reaction?

Accepted Answer

A tertiary alkyl bromide

Question 4

Why does a strong nucleophile prefer to attack a less crowded carbon in an SN2 reaction?

Accepted Answer

Steric hindrance slows down the reaction at crowded sites

Question 5

Which of the following is a strong oxidizing agent used to convert primary alcohols to carboxylic acids?

Accepted Answer

H2CrO4

Question 6

In the reaction $$ \mathrm{CH_3C\equiv CH} + \mathrm{$$NaNH_2$$} \rightarrow \mathrm{CH_3C\equiv C^-} + \mathrm{NH_3$} $$, why is NaNH2 used?

Accepted Answer

NaNH2 is a strong base that can deprotonate the terminal alkyne

Question 7

Which statement best explains why lower energy transition states react faster in organic reactions?

Accepted Answer

Lower energy transition states have smaller activation barriers

Question 8

What is the role of a weak base in the deprotonation of a terminal alkyne?

Accepted Answer

A weak base will not deprotonate the alkyne efficiently

Question 9

Which of the following is true about SN1 reactions?

Accepted Answer

They proceed faster with strong electrophiles and weak nucleophiles

Question 10

In the context of acid/base strength, which statement is correct?

Accepted Answer

A stronger acid has a weaker conjugate base

Question 11

Which of the following best describes the effect of steric hindrance on nucleophilic substitution reactions?

Accepted Answer

Steric hindrance decreases the rate of SN2 reactions

Question 12

If you want to selectively oxidize a primary alcohol to an aldehyde without further oxidation, which reagent should you use?

Accepted Answer

PCC

Question 13

Which of the following is most likely to deprotonate a terminal alkyne?

Accepted Answer

$$ \mathrm{$$NaNH_2$$} $$

Question 14

What is the expected product when a benzene ring undergoes substitution with a methyl group?

Accepted Answer

The methyl group replaces a hydrogen atom on the benzene ring

Question 15

Which factor most strongly influences the rate of an SN2 reaction?

Accepted Answer

Steric accessibility of the electrophilic carbon

Question 16

Why is a tertiary alkyl halide less reactive in SN2 reactions?

Accepted Answer

It is more sterically hindered, making nucleophilic attack difficult

Question 17

Which of the following statements about nucleophiles is correct?

Accepted Answer

Strong nucleophiles prefer less crowded (less sterically hindered) sites

Question 18

In the reaction $$ \mathrm{CH_3C\equiv CH} + \mathrm{$$NaNH_2$$} \rightarrow \mathrm{CH_3C\equiv C^-} + \mathrm{NH_3$} $$, what is the driving force?

Accepted Answer

Formation of a weaker base ($$ \mathrm{NH_3$} ) $$from a stronger base ($$ \mathrm{$$NaNH_2$$} )$$

Organic Chemistry: Substitution, Oxidation, Alkyl Halide Reactivity, and Acid-Base Strength

Study Guide - Practice Questions