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Chapter 2: Q 53P (page 141)

Question: 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)3N

(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, BF3

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

Question: The C 鈮� Ntriple bond in acetonitrile has a dipole moment of about 3.6 Dand a bond length of about 1.16 脜. Calculate the amount of charge separation in this bond. How important is the charge separated resonance form in the structure of acetonitrile?

Classify the following hydrocarbons, and draw a lewis structure for each one. A compound may fit into more than one of the following classifications:

Alkane, alkene, alkyne, cycloalkane, cycloalkene, cycloalkyne, aromatic hydrocarbon.

  1. (CH3CH2)2CHCH(CH3)2
  2. CH3CHCHCH2CH3
  3. CH3CCCH2CH2CH3

e.

f.

g.

h.

i.

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)

(i)

(j)

(k)

(l)

Question: 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

Acetic acid can also react as a very weak base (pKb). Two different site son acetic acid might become protonated to give the conjugate acid. Draw both of these possible conjugate acids, and explain (resonance) why the correct one is stable. Calculate the pKaof this conjugate acid.
See all solutions

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