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Magazine Chapter 12: PROBLEM 12.6 (page 460)
Question: Given that syn addition of H2 occurs from both sides of a trigonal planar double bond, draw all stereoisomers formed when each alkene is treated with H2 .
a.
b.
c.
Short Answer
Answer
a.
b.
c.
Step by step solution
Stereospecific reactions
If by taking a stereochemically different product (cis or trans), a stereospecific product is obtained, then such a reaction is called a stereospecific reaction.
The addition of molecular hydrogen to an alkene is an example of a stereospecific reaction.
Stereochemistry of addition of molecular H2 to an alkene
When a cis stereomer is subjected to molecular hydrogenation in the presence of a catalyst, a single product is formed, stereochemically meso.
When a cis stereo is subjected to molecular hydrogenation in the presence of a catalyst, two different products are obtained in equal amounts. They are enantiomers of each other, and therefore the overall product is a racemic mixture.
Hydrogenation of an alkene
a. The product obtained is a racemic mixture of two enantiomers (mirror image).
Hydrogenation reaction of alkene resulting product as a racemic mixture
b. The products obtained are diastereomers (non-mirror image).
Hydrogenation reaction of alkene resulting meso product
c. The products obtained are diastereomers (non-mirror image).
Hydrogenation reaction of alkene resulting in meso product
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