Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 9 - Alkynes - Problems - Page 410: Problem 9-18 e

Answer

The picture is attached below.

Work Step by Step

Hex-1-yne, when reacted with $H_{2}$ and $HBr$, forms 2-bromohexane. 2-bromo means the presence of one bromine atom at carbon number 2. The triple bond in hex-1-yne found between carbon number 1 and carbon number 2 breaks, and the bond between $H-H$ also breaks in the presence of lindlar's catalyst. $H$ atoms attach with these carbons and form a single bond with carbon number 1 and carbon number 2. In this way, the triple bond is converted into a double bond. Furthermore, when the above formed product is reacted with $H-Br$, the double bond between the carbon atoms breaks. H and Br atoms attach with these carbons and form a single bond with this carbon. Bromine attaches to carbon number 2 whereas Hydrogen forms a bond with carbon number 1. In this way, the double bond is converted into a single bond and hence, 2-bromohexane is formed.
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