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Chapter 11: Q56b (page 350)

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

b. (CH3)3 CCI (CH3)3 CBr (CH3)3 COH

Short Answer

Expert verified

Answer

b. (CH3)3 COH <(CH3)3 CCI <(CH3)3 CBr

Step by step solution

01

  SN2 reaction

It is the substitution nucleophilic unimolecular reaction. It follows first-order kinetics that it is a two-step reaction in which a carbocation intermediate is formed.

The rate of the reaction depends only on the reacting species is independent of the nucleophile.

02

Reactivity towards SN2 reaction

As the carbocation intermediate is formed in the reaction the reacting species which form the most stable carbocation is more reactive toward the nucleophile.

Stability of carbocation:

  1. 30 > 20 > 10
  2. If carbocation showing resonance is more stable than non-resonance carbocation
  3. The best leaving group forms the most stable carbocation as in halogen Br is the best-leaving group then Cl and OH is the poor leaving group.

So,

(CH3)3 COH < (CH3)3 CCI < (CH3)3 CBr

Reactivity order

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Most popular questions from this chapter

Question: (R)-2-Bromooctane undergoes racemization to give (卤)-2-bromooctane when treated with NaBr in dimethyl sulfoxide. Explain.

The following tertiary alkyl bromide does not undergo a nucleophilic substitution reaction by either SN1 or SN2 mechanisms. Explain.

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

(a)

(b)

Methyl esters (RCO2CH3) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethylformamide:

The following evidence has been obtained: (1) The reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester (RCO2CH2CH3) cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support your hypothesis?

What alkyl halides might the following alkenes have been made from ?

(a)

(b)
See all solutions

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