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Rank the following compounds in decreasing order of their

Chapter 8, Problem 18P

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QUESTION:

Rank the following compounds in decreasing order of their reactivity toward the \(S_{N} 2\) reaction with sodium ethoxide \(\left(\mathrm{Na}^{+}-\mathrm{OCH}_{2} \mathrm{CH}_{3}\right)\) in ethanol.


methyl chloride              
tert-butyl iodide           neopentyl bromide
isopropyl bromide         methyl iodide
              ethyl chloride

Problem-solving Hint

Do not write \(S_{N} 2\)  reactions occurring on tertiary alkyl halides.

Equation Transcription:

Text Transcription:

S_N2

(Na+-OCH_2CH_3)

SN2

Questions & Answers

QUESTION:

Rank the following compounds in decreasing order of their reactivity toward the \(S_{N} 2\) reaction with sodium ethoxide \(\left(\mathrm{Na}^{+}-\mathrm{OCH}_{2} \mathrm{CH}_{3}\right)\) in ethanol.


methyl chloride              
tert-butyl iodide           neopentyl bromide
isopropyl bromide         methyl iodide
              ethyl chloride

Problem-solving Hint

Do not write \(S_{N} 2\)  reactions occurring on tertiary alkyl halides.

Equation Transcription:

Text Transcription:

S_N2

(Na+-OCH_2CH_3)

SN2

ANSWER:

Solution 18P

Factors that affect the rate of  reactions are as follows:

1. Nature of leaving group

2. Nature of the substrate

Weak bases are good leaving groups. In halogens, the leaving group order is as follows:

The substrate with less steric hindrance has a high reactivity towards the  reaction.

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