Exam 5

Question 1

A carboxylic acid is MORE reactive in nucleophilic acyl substitution if its leaving group is a _____ base.

Answer 1

weaker

Question 2

Why is a carboxylic acid more reactive in NAS if the LG is a weaker base?

Answer 2

• A stronger base stabilizes the carb. acid derivative, making it less reactive
• A stronger base is a worse LG

Question 3

What can acid chloride convert to? What is the basicity of acid chloride? How electrophilic is it?

Answer 3

• It can convert to anhydride, ester, carb acid, or amide (all)
• It is a WEAK base
• It is very electrophilic

Question 4

What can anhydride convert to? What is the basicity of anhydride? How electrophilic is it?

Answer 4

• It CANNOT convert to acid chloride but CAN convert to ester, carb. acid, or amide
• It is second weakest base
• It is second highest electrophilic

Question 5

What can ester convert to? What is the basicity of ester? How electrophilic is it?

Answer 5

• It CANNOT convert to acid chloride or anhydride
• CAN convert to carb acid or amide
• it is a medium base (behind acid chloride and anhydride)
• It is medium electrophilic

Question 6

What can carboxylic acid convert to? What is the basicity of carboxylic acid? How electrophilic is it?

Answer 6

• It CANNOT convert to acid chloride, anhydride, or ester
• CAN only convert to amide
• it is a strong base (second strongest behind amide)
• It is a weak electrophile

Question 7

What can amide convert to? What is the basicity of amide? How electrophilic is it?

Answer 7

• It CANNOT convert to acid chloride, anhydride, ester, or carb. acid
• Can’t convert to anything
• it is a very strong base (strongest)
• It is a very weak electrophile (weakest)