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Chapter 2: Q51 P (page 141)

In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reaction. Draw any nonbonding electrons to show how they participate in the reactions.

(a)

(b)

(c)

(d)

(e)

Short Answer

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(a)

(b)

(c)

(d)

(e)

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

Reactions showing movement of electron pairs

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

(a)

(b)

(c)

(d)

(e)

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Most popular questions from this chapter

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.

Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with strong nucleophile sodium ethoxide, Na+ - OCH2CH3.

(a)

(b)

NH+4

(c)

CH3CH2Br

(d)

BH3

(e)

CH3COOH

(f)

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

Dimethyl ether and ethanol are isomers. Their boiling points are very different, however. Explain why these two compounds have dramatically different boiling points.

CH3-O-CH3 CH3CH2-OH

dimethyl ether, bp -24 °C ethanol, bp 78 °C
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