18.4.1 Nucleophilic Substitution at sp3 Carbon

Question 1

In a nucleophilic substitution reaction, which of the following is the best leaving group?

Answer 1

Weaker bases

Question 2

What is a nucleophile?

Answer 2

Electron pair donor

Question 3

The following reaction occurs in aqueous solution. Identify the nucleophile (Lewis base) and the leaving group.

OH − + CH3Cl → CH3OH + Cl −

Answer 3

Nucleophile: OH −

Leaving group: Cl −

Question 4

Which of the following best defines a carbocation?

Answer 4

A substance that contains a carbon with an empty p orbital.

Question 5

In the following reaction progress chart, identify the rate-determining step.

Answer 5

TS2

Question 6

In a nucleophilic substitution reaction, the nucleophile X replaces the leaving group Y. Which statement best describes how the bond between C and X breaks and how the bond between C and Y forms?

Answer 6

The C–X bond breaks heterolytically and the C–Y bond forms heterolytically.

Question 7

The covalent bond between two atoms is cleaved so that both electrons stay with one fragment. What is this known as?

Answer 7

Heterolytic cleavage

Question 8

Which of the following is most likely to be a nucleophile?

Answer 8

Question 9

Which of the following are potential nucleophiles?

Answer 9

Anions

Question 10

Which of the following is most likely to be an electrophile?

Answer 10

AlCl3