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Question
Give reason for the following:
The product formed during SN1 reaction is a racemic mixture.
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Solution
During the SN1 mechanism, intermediate carbocation formed is sp2 hybridized and planar in nature. This allows the attack of nucleophiles from either side of the plane resulting in a racemic mixture.
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RELATED QUESTIONS
Which would undergo SN2 reaction faster in the following pair and why ?
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Which of the following undergoes nucleophilic substitution exclusively by SN1 mechanism?
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(i)
(ii)
CH3CH2CH2Cl
(iii)
\[\begin{array}{cc}
\ce{CH3}\phantom{..}\\
|\phantom{....}\\
\ce{CH3-CH-CH2Cl}
\end{array}\]
(iv)
\[\begin{array}{cc}
\phantom{..}\ce{H}\\
\phantom{..}|\\
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\phantom{..}|\\
\phantom{.....}\ce{C2H5}
\end{array}\]
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(iii) Molecularity of reaction is one.
(iv) Molecularity of reaction is two.
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\[\ce{CH3-CH2-Cl}\] or \[\ce{C6H5-CH2-Cl}\]
Consider the reactions,
(i) \[\begin{array}{cc}
\phantom{}\ce{\underset{}{(CH3)2CH - CH2Br} ->[C2H5OH] \underset{}{(CH3)2CH - CH2OC2H5 + HBr}}\\
\end{array}\]
(ii) \[\begin{array}{cc}
\phantom{}\ce{\underset{}{(CH3)2CH - CH2Br} ->[C2H5O-] \underset{}{(CH3)2CH - CH2OC2H5 + Br-}}\\
\end{array}\]
The mechanisms of reactions (i) and (ii) are respectively:
