Question
Asked Nov 24, 2019
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14. Please show the step by step solution. 

Deternine the major organic product for the following reaction scheme:
1. 2LI, Et,O
Br
2. CH,СНC-CH
3. СH CH,,
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Deternine the major organic product for the following reaction scheme: 1. 2LI, Et,O Br 2. CH,СНC-CH 3. СH CH,,

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Expert Answer

Step 1

In presence of ether, lithium reacts with alkyl halide which results in the formation of alkyl lithium compound. Lithium releases free electrons when reacts with alkyl halide and these electrons help in breaking of C-Cl bond. The product formed by the reaction of bromocyclopentane with lithium metal is shown below.

Br 2Li
. Li
-
Et2O
bromocyclopentane
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Br 2Li . Li - Et2O bromocyclopentane

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Step 2

In the next step, the hydrogen of alkyne behaves as an acidic proton which results in the formation of cyclohexane. The alkyl lithium has high affinity for proton. Thus, the reaction of alkyl lithium with the given alkyne is shown below.

(CHJCH-C—с-н
(CH)CH-С— CLi
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(CHJCH-C—с-н (CH)CH-С— CLi

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Step 3

The next step is the nucleophilic substitution step. In this step, removal of chlorine...

+ CH;CH>—Cн,
(CH),CНC—C
(CH),CНC С—Li
LiC
Н.С— (сH).
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+ CH;CH>—Cн, (CH),CНC—C (CH),CНC С—Li LiC Н.С— (сH).

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