Question 1

Which of the following statements best explains why tert-butyl chloride ionizes fastest in water compared to the other solvents listed in the table?

Accepted Answer

Water is a polar protic solvent with a high dielectric constant, which stabilizes both the carbocation and the leaving group through hydrogen bonding.

Question 2

Based on the data in the table, which solvent would you expect to give the slowest rate of ionization for tert-butyl chloride, and why?

Accepted Answer

Diethyl ether, because it is an aprotic solvent with a very low dielectric constant and cannot stabilize ions effectively.

Question 3

What is the main reason polar protic solvents increase the rate of SN1 reactions such as the ionization of tert-butyl chloride?

Accepted Answer

They stabilize the carbocation intermediate and the leaving group through hydrogen bonding.

Question 4

Given the following solvents: water, methanol, ethanol, acetone, and diethyl ether, which would be most suitable for maximizing the rate of an SN1 reaction involving tert-butyl chloride?

Accepted Answer

Water, because it is a polar protic solvent with the highest dielectric constant.

Question 5

If you were to perform the ionization of tert-butyl chloride in ethanol at 25°C, what would be the relative rate compared to water, based on the table?

Accepted Answer

$$1/40$$

Question 6

Which property of a solvent is most directly correlated with its ability to stabilize ions in solution, thereby increasing the rate of SN1 reactions?

Accepted Answer

Dielectric constant

Question 7

Why does acetone, despite being a polar solvent, result in a much slower rate of tert-butyl chloride ionization compared to water?

Accepted Answer

Acetone is a polar aprotic solvent and cannot stabilize the carbocation intermediate or the leaving group as effectively as a polar protic solvent.

Question 8

Which of the following best describes the trend in relative rates of tert-butyl chloride ionization as the dielectric constant of the solvent decreases?

Accepted Answer

The rate decreases as the dielectric constant decreases.

Question 9

A student wants to perform an SN1 reaction with tert-butyl chloride and observes that the reaction is extremely slow in diethyl ether. What is the most likely explanation?

Accepted Answer

Diethyl ether is an aprotic solvent with a low dielectric constant, so it does not stabilize the carbocation or the leaving group.

Question 10

Which solvent would you choose to slow down the rate of ionization of tert-butyl chloride as much as possible, and why?

Accepted Answer

Diethyl ether, because it is aprotic and has the lowest dielectric constant among the options.

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions (Chapter 7 Study Notes)

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