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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

SN2 reactions take place with inversion of configuration, andSN1 reactions take place with racemization. The following substitution reaction, however, occurs with complete retention of configuration. Propose a mechanism.

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Ethers can often be prepared by SN2 reaction of alkoxide ions,RO- ,with alkyl halides. Suppose you wanted to prepare cyclohexyl methylether. Which of the two possible routes shown below would youchoose? Explain.

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Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

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