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Chapter 11: Q57c (page 350)

Question: Order each of the following sets of compounds with respect to reactivity:

c. CH3CH2 CH2OCH3 CH3CH2 CH2OTs CH3CH2 CH2Br

Short Answer

Expert verified

Answer

CH3CH2 CH2OCH3 < CH3CH2 CH2 Br < CH3CH2 CH2OTs

Step by step solution

01

SN2 reaction

It is a nucleophilic substitution reaction in which old bond is break and new bond is formed both the process occur simultaneously. Hence, it’s a single step reaction.

The two reacting species are involved in the rate determining steps.

02

Reactivity towards  SN2 reaction

As the reaction is single step reaction so, no intermediate is formed andSN2 occur fast with primary alkane than secondary alkane.

SN2 occur fast with those reacting species which have best leaving group

OTs is one of the best leaving group then halogens are the good leaving group

So,

CH3CH2 CH2OCH3 < CH3CH2 CH2 Br < CH3CH2 CH2OTs

Reactivity order

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Most popular questions from this chapter

From which alkyl bromide was the following alkyl acetate made SN2 byreaction? Write the reaction, showing all stereochemistry.

Which reactant in each of the following pairs is more nucleophilic? Explain.

(e) I- or Cl-

Metabolism of S-adenosylhomocysteine (Section 11-6) involves the following sequence. Propose a mechanism for the second step.

Write the product you would expect from reaction of each of the following alkyl halides with (1)Na+-SCH3and (2)Na+-OH (green = Cl):

c)

Predict whether each of the following substitution reactions is likely to be SN1orSN2:

(a)

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