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Question
Given reasons: SN1 reactions are accompanied by racemization in optically active alkyl halides.
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Solution
In SN1 reaction, formation of carbocation as an intermediate takes place. This carbocation has sp2-hybridised and planar structure. This planar carbocation is attacked by nucleophile from both the sides equally to form d and l isomers in equal proportion. Such products are called racemic mixture. Hence, SN1 reactions are accompanied by racemisation in optically active alkyl halides.
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In the following pair of halogen compounds, which compound undergoes a faster SN1 reaction?
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\[\ce{CH3CH2CH2OH + SOCl2 ->}\]
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A primary alkyl halide would prefer to undergo ______.
Match the reactions given in Column I with the types of reactions given in Column II.
| Column I | Column II | |
| (i) |  |
(a) Nucleophilic aromatic substitution |
| (ii) | \[\begin{array}{cc} \ce{CH3 - CH = CH2 + HBr -> CH3 - CH - CH3}\\ \phantom{............................}|\phantom{}\\ \phantom{.............................}\ce{Br}\phantom{} \end{array}\] |
(b) Electrophilic aromatic substitution |
| (iii) |  |
(c) Saytzeff elimination |
| (iv) |  |
(d) Electrophilic addition |
| (v) | \[\begin{array}{cc} \ce{CH3 CH2 CH CH3 ->[alc.KOH] CH3 CH = CH CH3}\\ \phantom{}|\phantom{..........................}\\ \phantom{}\ce{Br}\phantom{........................} \end{array}\] |
(e) Nucleophilic substitution (SN1) |
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Which alkyl halide from the following pair would you expect to react more rapidly by an SN2 mechanism? Explain your answer.
\[\begin{array}{cc}\ce{CH3CH2CHCH3}\\\phantom{...}|\\\phantom{....}\ce{Br}\end{array}\] or \[\begin{array}{cc}\phantom{.....}\ce{CH3}\\\phantom{..}|\\\ce{H3C - C - Br}\\\phantom{..}|\\\phantom{....}\ce{CH3}\end{array}\]
