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Question

Show by means of reactions, how you will inter-convert cis-trans isomers of hex-3-ene?

A
1. Br2/CCl4; 2.NaNH2/NH3 3. Lindlar Pd/C H2 for cis; Li,NH3 for trans
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B
1. Br2/CCl4; 2.NaNH2/NH3 3. Lindlar Pd/C H2 for trans; Li,NH3 for cis
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C
1. Br2/CCl4; 2.NaNH2/NH3 3. Lindlar Pd/C H2 for trans; Na,NH3 for cis
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D
1. Br2/CCl4; 2.NaNH2/NH3 3. Lindlar Pd/C H2 for cis; Na,NH3 for trans
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Solution

The correct options are
A 1. Br2/CCl4; 2.NaNH2/NH3 3. Lindlar Pd/C H2 for cis; Li,NH3 for trans
D 1. Br2/CCl4; 2.NaNH2/NH3 3. Lindlar Pd/C H2 for cis; Na,NH3 for trans
Start with any isomer and bromine addition across the double bond of hex-3-ene gives 3,4-dibromohexane.

From the above compound, get to hex-3-yne by dehydrohalogenation:

Getting to hex-3-yne is the key. From there it is easy!

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