Solution Found!
Drawing on what you know about the stereochemistry of
Chapter 7, Problem 13P(choose chapter or problem)
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.