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Drawing on what you know about the stereochemistry of

Chapter 7, Problem 13P

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QUESTION:

Problem 13P

Drawing on what you know about the stereochemistry of alkene addition reactions:

a. write the mechanism for the reaction of 2-butyne with one equivalent of Br2.

b. predict the configuration of the product of the reaction.

Questions & Answers

QUESTION:

Problem 13P

Drawing on what you know about the stereochemistry of alkene addition reactions:

a. write the mechanism for the reaction of 2-butyne with one equivalent of Br2.

b. predict the configuration of the product of the reaction.

ANSWER:

Solution 13P

Step 1 of 2:

a. Here, we are asked to write the mechanism for the reaction of 2-butyne with one equivalent of Br2.

The mechanism for the reaction of 2-butyne with one equivalent of Br2 is as shown below:

This above reaction is the electrophilic addition of a hydrogen halide to an alkyne. Bromination of 2-butyne forms trans-2,3-dibromo-2-butyne as shown above. The addition of Br2 is an anti addition because the two bromine atoms add to opposite sides of the double bond of 2-butyne, which results in the formation of trans-isomer of the compound.


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