Question 1

Which of the following radicals is the most stable due to resonance stabilization?

Accepted Answer

Benzyl radical

Question 2

In an $$S_N1$$ reaction, which of the following compounds will react the fastest?

Accepted Answer

2-bromo-2-methylpropane

Question 3

Which of the following anions is most stabilized by delocalization of negative charge?

Accepted Answer

Cyclopentadienyl anion

Question 4

When cyclohexane is brominated under photolytic conditions ($$Br_2$$, $$hv$$), what is the major monobrominated product?

Accepted Answer

2-bromocyclohexane

Question 5

Which compound will react the slowest in a photolytic bromination ($$Br_2$$, $$hv$$)?

Accepted Answer

Cyclopropane

Question 6

In an $$S_N2$$ reaction, which of the following alkyl halides will react fastest with $$NaCN in $$ethanol?

Accepted Answer

Primary alkyl chloride

Question 7

If the concentration of $$NaCl in $$ethanol is increased from $$0.01 M to$$ $$0.1 M$$, how will the rate of an $$S_N1$$ reaction change?

Accepted Answer

Not change

Question 8

Which of the following best describes the product of an E2 elimination of methyl chloride (A) with sodium ethoxide in ethanol?

Accepted Answer

The most substituted alkene (Zaitsev product)

Question 9

Which compound reacts faster in a show E2 reaction: methyl chloride (A) or neopentyl chloride (B)?

Accepted Answer

Neopentyl chloride (B)

Question 10

Assign the E/Z configuration to the following alkene: $$CH_3CH=$$CHCH_3$$

Accepted Answer

Z

Question 11

Which of the following reagents would best convert benzyl bromide to benzyl methyl sulfide ($$PhCH_2SCH_3$$)?

Accepted Answer

$$CH_3SH$$

Question 12

Which of the following statements about $$S_N2$$ reactions is correct?

Accepted Answer

The rate depends on both the substrate and nucleophile concentrations

Question 13

Which of the following is a correct statement about the Zaitsev rule in E2 eliminations?

Accepted Answer

The most substituted alkene is favored

Question 14

What is the expected product when 2-bromopentane reacts with $$NaOEt in $$ethanol?

Accepted Answer

Pent-2-ene

Question 15

Which of the following best explains why tertiary alkyl halides do not undergo $$S_N2$$ reactions efficiently?

Accepted Answer

Steric hindrance prevents nucleophilic attack

Question 16

Which of the following is the major product when 2-chloropentane reacts with $$NaI in $$acetone?

Accepted Answer

2-iodopentane

Question 17

Which of the following is true about the E2 reaction mechanism?

Accepted Answer

It requires a strong base and a good leaving group

Question 18

What is the effect of replacing chlorine with bromine in an $$S_N2$$ reaction?

Accepted Answer

The rate increases

Question 19

Which of the following best describes the product of the reaction of 1-bromocyclohexane with $$NaOEt$$?

Accepted Answer

Cyclohexene

Question 20

Which of the following is the correct E/Z configuration for the alkene $$CH_3CH=CHCOOH$$?

Accepted Answer

E

Organic Chemistry II: Radical Stability, Substitution & Elimination Mechanisms, and Alkene Stereochemistry

Study Guide - Practice Questions