Chapter 6 Solutions

In-chapter exercises

E6.1:

E6.2:

E6.3

End-of-chapter problems

P6.1:

Left side: the nucleophile is an amine, the electrophile is the methyl carbon, and the leaving group is a sulfide.

Right side: The nucleophile is a thiolate ion, the electrophile is the carbon atom of an alkyl diphosphate, and diphosphate is the leaving group.

P6.2:

a)

b) In step 1, the nucleophile is the hydroxide oxygen, and the electrophile is the carbonyl carbon of the thioester.

P6.3:

a)

b)

c)

d)

e)

f) Bold dots show the two carbons that form a new bond in this reaction step.

P6.4:

The C to D step has the highest activation energy, and thus is the slowest, rate-determining step.

P6.5:

Contributors

• Organic Chemistry With a Biological Emphasis, Tim Soderberg (University of Minnesota, Morris)