Question 1

Which reagent would you use to carry out the elimination step in the first reaction sequence (from 2-bromopropane to propene)?

Accepted Answer

$$\mathrm{KOH} ($$alcoholic)

Question 2

In the first reaction sequence, what is the major product of the addition of HBr to propene?

Accepted Answer

2-bromopropane

Question 3

What type of mechanism is involved in the elimination step shown in the first image?

Accepted Answer

E2

Question 4

In the second reaction sequence, what is the role of HBr in the addition step to methylcyclohexene?

Accepted Answer

It adds Br to the more substituted carbon (Markovnikov)

Question 5

After the elimination step in the second sequence, where is the double bond located in the final product?

Accepted Answer

At the position adjacent to the original methyl group

Question 6

Which of the following best describes the regiochemistry of the addition of HBr to an alkene?

Accepted Answer

Br adds to the more substituted carbon (Markovnikov rule)

Question 7

What is the purpose of performing an elimination followed by an addition in these sequences?

Accepted Answer

To move the position of the functional group or double bond

Question 8

Which base would be most appropriate for the elimination step to favor the Zaitsev product?

Accepted Answer

$$\mathrm{EtONa} ($$ethoxide in ethanol)

Question 9

If you wanted to move the double bond to a different position in the ring (as in the second image), which sequence would you use?

Accepted Answer

Addition of HBr, then elimination with a strong base

Question 10

Which of the following statements about the elimination-addition sequence is correct?

Accepted Answer

The sequence can be used to move a halogen atom to a different carbon

Question 11

What is the product when 2-bromopropane undergoes elimination with $$\mathrm{KOH} ($$alcoholic) followed by addition of HBr?

Accepted Answer

2-bromopropane

Question 12

Which of the following is a correct statement about the mechanism of the elimination step in these sequences?

Accepted Answer

It is a concerted process where the base removes a proton as the leaving group departs

Organic Synthesis: Strategies, Functional Group Transformations, and Retrosynthetic Analysis

Study Guide - Practice Questions