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Question

CH3CCHNaNH2−−−−XCH2CH2Br−−−−−−Y. Identify the product 'Y' is


A

Pent - 2 - ene

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B

Pent - 2 - yne

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C

Pent - 1 - yne

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D

Pentane

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Solution

The correct option is B

Pent - 2 - yne


X is CH3CCNa+

Y is CH3CCCH2CH3

The first step removes the terminal hydrogen from the given substrate (reactant on the left). Such a removable hydrogen is called an acidic hydrogen. In the next step, the nucleophile - which is rich in electrons - attacks the CBr bond of ethyl bromide. Because of the difference in electronegativity between carbon and bromine, this CBr bond is polar - meaning, the bonding electrons are closer to the more electronegative bromine. This gives rise to the possibility of the carbon of the CBr bond having a slight deficit of electrons; let's just say that this carbon misses electrons and that is where the electron-rich terminal carbon of CH3CC comes in. Hence, the reaction.


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