Ch. 20 – Carboxylic Acids / Derivatives & Nucleophilic Acyl Substitution

Question 1

How does the basicity of Z in RCOZ affect compound reactivity?

Answer 1

the more basic Z is, the more stable RCOZ is (due to resonance) and the less reactive the compound is (ex. Cl is the least basic and is the best LG, acyl chlorides are the most reactive compared to OR or NR2)

Question 2

What is the pKa of a protonated C.A. derivative?

Answer 2

-6 to -7

Question 3

Why do amides have more H-bonding that carb acids and alcohols?

Answer 3

they have H bonding but can also form a pseudo salt bridge due to resonance (the salt bridge form is more prevalent in amides)

Question 4

What name ending is used for acyl chlorides?

Answer 4

chain = -oyl chloride
ring = carbonyl chloride

Question 5

What name ending is used for esters?

Answer 5

chain = -oate
ring = carboxylate

Question 6

What name ending is used for anhydrides?

Answer 6

anhydride

Question 7

What name ending is used for amides?

Answer 7

amide

Question 8

What name ending is used for lactones (cyclic esters)?

Answer 8

naming O = -oxa-

ending = -one

Question 9

What name ending is used for lactams (cyclic amides)?

Answer 9

naming N = -aza-

ending = -one

Question 10

What name ending is used for naming nitriles?

Answer 10

chain = nitrile
ring = carbonitrile

Question 11

Name the list of priorities for naming (greatest to least)?

Answer 11

carb acid > esters > amides > nitriles > aldehydes > ketones > alcohols > amines > alkenes + alkynes

Question 12

What is the list of reactivity (and having better LG) for carb acid derivatives? (in order)

Answer 12

acyl chloride > anhydride > ketone = aldehyde > ester = carb acid > amide