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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

Draw the structure and assign Z or E stereochemistry to the product you expect from E2 reaction of the following molecule with NaOH (green = Cl):

What product would you expect to obtain from SN2 reaction of OH-with (R)-2-bromobutane? Show the stereochemistry of both the reactant and product.

Which compound in each of the following pairs will react faster in an SN2reaction with?

a) CH3Br or CH3I

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

a) NH2-or NH3

The following Walden cycle has been carried out. Explain the results, and indicate where Walden inversion occurs.
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