Solution Found!
Solved: Starting with ethyne, describe how the following
Chapter 7, Problem 57P(choose chapter or problem)
Problem 56P
Starting with ethyne, describe how the following compounds could be synthesized:
a. (3S,4R)- 4-bromo-3-hexanol and (3R,4S)- 4-bromo-3-hexanol
b. (3R,4R)- 4-bromo-3-hexanol and (3S,4S)- 4-bromo-3-hexanol
Questions & Answers
QUESTION:
Problem 56P
Starting with ethyne, describe how the following compounds could be synthesized:
a. (3S,4R)- 4-bromo-3-hexanol and (3R,4S)- 4-bromo-3-hexanol
b. (3R,4R)- 4-bromo-3-hexanol and (3S,4S)- 4-bromo-3-hexanol
ANSWER:
Solution 56P:
Here, we are going to write the synthesizing steps to prepare the following product by using the appropriate reagents.
Step 1:
a. (3S,4R)- 4-bromo-3-hexanol and (3R,4S)- 4-bromo-3-hexanol
Here, acetylene reacts with amide to form acetylide ion which on react with corresponding ethyl bromide to form 1-butyne. Secondly, in similar way, 1-butyne reacts with amide to form acetylide ion which react with ethyl bromide to form 3-hexyne. Finally, 3-hexyne undergo hydrogenation reaction in presence of Na/Li in liquid NH3 to form the trans-3-hexene as a product. Finally, trans-3-hexene reacts with Br2 water to form the final products.
The reaction steps are given below:
