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Organic Chemistry
Found in: Page 453

Short Answer

Question: Devise a synthesis of the following compound from cyclohexene and acetylene. You may use any other inorganic reagents.


The + enantiomer is prepared by the following steps:

Formation of acetylide anion

Conversion of cyclohexene to epoxide

Synthesis of + enantiomer

See the step by step solution

Step by Step Solution

Step-by-Step AnswerStep 1: Synthesis of organic compounds from acetylide anions

The acetylide anions are used as the starting material for the synthesis of several organic compounds. The acetylide anions are very reactive and act as strong nucleophiles. They are very strong bases.

There is a presence of a negative charge on the carbon atom due to the presence of a lone pair of electrons. The acetylide anions are formed by using a strong base, which causes the deprotonation of the acetylene molecule.

The acetylide anions are strong nucleophiles and can displace the halide ions and other leaving groups in several substitution reactions.

Step 2: Synthesis of the + enantiomer from cyclohexene and acetylene

The + enantiomer can be synthesized from cyclohexene and acetylene. The acetylene is treated with a strong base to form acetylide anion in the following reaction:

Formation of acetylide anion

The cyclohexene is oxidized into the epoxide in the following way:

Conversion of cyclohexene to epoxide

The synthesis of the + enantiomer takes place by the following reaction:

Synthesis of + enantiomer

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