Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile, BF3.

(a)

(b)

(c)

(d)

(CH3)3H

(e)

CH3CH2OH

(f)

(CH3 )2S

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Lewis concept of acid and base

According to Lewis, an acid can be defined as any molecule, ion or radical which can accept one or more electron pairs, that is, an acid is an electron pair acceptor. A Lewis base can be defined as any molecule, ion or radical which can donate one or more electron pairs, that is, a base is an electron pair donor.

02

Electrophiles and nucleophiles

Lewis acid accepts a pair of electrons, hence it can be called as electrophiles which means electrons loving. Also, Lewis base donates a pair of electrons, hence it can be called as nucleophiles which means nuclei loving.

03

Curved arrow mechanism showing how the given compounds (nucleophile) react with strong electrophile, 

Curved arrows are used to show the movement of electrons from the nucleophile (Lewis base) to the electrophile (Lewis acid).

(a)


(nucleophile) (electrophile)

(b)

(nucleophile) (electrophile)

(c)

(nucleophile) (electrophile)

(d)

(nucleophile) (electrophile)

(e)

(nucleophile) (electrophile)

(f)

(nucleophile) (electrophile)

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Most popular questions from this chapter

The pKa of ascorbic acid (vitamin C, page 9) is 4.17 , showing that it is lightly more acidic than acetic acid (CH3COOH,pKa =4.74) .

(a)Show four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.

(b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.

(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH ) group

Predict the products of the following acid-base reactions.

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(b)

(c)

(d)

(e)

(f)

(g)

(h)

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

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(j)

(k)

(l)

N-Methylpyrrolidine has a boiling point of81οC, and piperidine has a boiling point of106οC.

  1. Explain the large difference (25οC) in boiling point for these two isomers.
  2. Tetrahydropyran has a boiling point of 88οC, and cyclopentanol has a boiling point of 141οC. These two isomers have a boiling point difference of 53οC.Explain why the two oxygen-containing isomers have a much larger boiling point difference than two amine isomers.
  3. N,N-Dimethylformamide has a boiling point of 150οC, and N-methylacetamide has a boiling point of 206οC, for a difference of 56οC.Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers. Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).

Rank the following acids in decreasing order of their acid strength. In each case, explain why the previous compound should be a stronger acid than the one that follows it.

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