Ch. 19 - Carboxylic Acids & Nitriles

Question 1

Do carboxylic acids have higher or lower bp/mp than other organic compounds?

Answer 1

higher; they have more IMFs

Question 2

What is the pKa of the acidic proton of carboxylic acid?

Answer 2

3-5

Question 3

What is the more nucleophilic oxygen on a carboxylic acid?

Answer 3

the oxygen double bonded to C; it has a partial negative charge in resonance hybrid

Question 4

What is the suffix given to name chain carboxylic acid molecules?

Answer 4

-oic acid

Question 5

What is given to name ring carboxylic acid molecules?

Answer 5

add carboxylic acid to the end

Question 6

What suffix is given to name carboxylate anions or carboxylic acid salts?

Answer 6

-oate

Question 7

How are dicarboxylic acids named?

Answer 7

add di- to -oic acid and retain parent “e”

Question 8

What is the IR stretch for C=O?

Answer 8

1710 cm^-1

strong, sharp

Question 9

What is IR stretch for OH?

Answer 9

2500-3500 cm^-1

strong, broad

Question 10

What is 1H NMR signal for carboxylic H?

Answer 10

10-12 ppm

broad singlet

Question 11

What is 1H NMR signal for H adjacent to carboxylic acid?

Answer 11

2-2.5 ppm

Question 12

What is 13C NMR signal for C=O?

Answer 12

120 ppm

Question 13

Why are carboxylic acids strong acids?

Answer 13

they have resonantly stabilized conjugate bases (weaker conj bases making acid more acidic)

Question 14

Is localized or delocalize charge more stable?

Answer 14

delocalized charge

Question 15

Does equlib favor production of stronger or weaker acid?

Answer 15

WEAKER acid or base

Question 16

An acid can be deprotonated by something with a (higher/lower) pKa?

Answer 16

higher

Question 17

Do EWGs EDGs increase acidity of carb acids and why?

Answer 17

EWG increase acidity because they stabilize the conjugate basic making the carb acid more acidic

Question 18

How does proximity affect the effects of EWGs and EDGs?

Answer 18

the closer the group, the stronger the effect

Question 19

If the pH of the environment is (higher/lower) than the pKa of the compound, it will stay acidic in solution.

Answer 19

if the pH is lower