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Rank the following compounds in decreasing order of their

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 18P Chapter 6

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 18P

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

Step-by-Step Solution:
Step 1 of 3

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.

The substrate reactivity order is as follows:

Methyl halides are most reactive towards the  reactions. So, among the given compounds, methyl halides are methyl chloride and methyl iodide.

Methyl iodide is most reactive towards the  reaction than methyl chloride. This is due to iodine is a good leaving group than chloride.

Among the given compounds, the primary halides are ethyl chloride and neopentyl bromide. Among the two alkyl halides ethyl chloride is most reactive towards  reaction.

Neopentyl bromide is also a primary alkyl halide. However, due to bulky nature of this substrate, it undergoes  reaction with the same rate of tertiary alkyl halide. Thus the reactivity of tert-butyl iodide and Neopentyl bromide are equal.

The isopropyl bromide is a secondary halide, whereas tert-butyl iodide is a tertiary halide. So, isopropyl bromide is more reactive towards the  reaction than tert-butyl iodide.

Thus the reactivity of SN2 reaction with sodium ethoxide in decreasing order is as follows:

Step 2 of 3

Chapter 6, Problem 18P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Rank the following compounds in decreasing order of their