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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

Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds and explain why the acidity increases so dramatically with substitution by nitro groups.

Give a definition and an example for each class of organic compounds.

(a) alkane

(b) alkene

(c) alkyne

(d) alcohol

(e) ether

(f) ketone

(g) aldehyde

(h) aromatic hydrocarbon

(i) carboxylic acid

(j) ester

(k) amine

(l) amide

(m) nitrile

Consider the following proposed Bronsted-Lowry acid-base reactions. In each case, draw the products of a transfer of the most acidic proton on the acid to the most basic site on the base. Use Appendix 4 to find the pKa values for the acids and the pKb values for the bases. Then determine which side of the reaction is favored, either reactants of products.

(a)

(b)

(c)

(d)

(e)

(f)

Draw the hydrogen bonding that takes place between

(a) two molecules of ethanol.

(b) two molecules of propylamine.

(c) a molecule of dimethyl ether and two molecules of water.

(d) two molecules of trimethylamine and a molecule of water.

Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

(a) Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. In each case, show the equation for the reaction with a generic base to give the conjugate base.

(b) Rank ethanol, methylamine, and acetic acid in decreasing order of basicity. In each case, show the equation for the reaction with a generic acid to give the conjugate acid.
See all solutions

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