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Predict the product and provide the complete electron-pushing mechanism for the following two-step synthetic processes:

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Step 1:General mechanism for addition of NaNH2 into alkyne

Addition of acetylene into NaNH2lead to abstraction of acidic hydrogen. Finally the reaction of haloalkane (RCH2Br)with anionic intermediate leads to the addition alkane group into the alkyne.

02

Formation of product in part (a)

Reaction of given reactant with NaNH2results into a formation of anionic intermediate

In the second step addition of methyl iodide takes place. Nucleophilic attack of methyl iodide (CH3I)and then addition of a methyl group into acetylene.

03

Formation of product in part (b)

Reaction of given reactant with NaNH2results into a formation of anionic intermediate

In the second step addition of Benzyl iodide (PhCH2I)takes place. Nucleophilic attack of Benzyl iodide and then addition of a Benzyl group into reactant.

04

Formation of product in part (c)

Reaction of given reactant with NaNH2results into a formation of anionic intermediate.

In the second step addition of methyl iodide (PhCH2I)takes place. Nucleophilic attack of Benzyl iodide and then addition of a benzyl group into butylene.

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(a)

(b)

(c)

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