Exam 2 Spec

Question 1

HNMR of

Benzylic protons
Aryl protons (bound to the phenyl)

Answer 1

Benzylic = 1.5-2.5 ppm

Aryl = 6.5-8 ppm

Question 2

HNMR of

Aldehylic protons
Alpha-carbonyl protons

Answer 2

Aldehylic = 9-10 ppm

Alpha = 2-2.5 ppm

Question 3

HNMR of

Carboxylic acid protons
Amide protons

Answer 3

Carboxyl = 12 ppm

Amide = 7.5-8.5 ppm

Question 4

IR of

Alkenes/arenas

Answer 4

3000-3150 cm-1

Question 5

IR of

Carbonyls
Aldehydic C-H proton

Answer 5

Carbonyls = ~1700 cm-1

Aldehydic = ~2700-2800

Question 6

IR of

Amide
Nitriles

Answer 6

Amide = ~1600 cm-1

Nitrile = ~2200 cm-1

Question 7

IR of

Acyl Chloride
Carboxylic acids

Answer 7

Acyl Chloride = 1800 cm-1

Carboxylic acid = 1760 cm-1

Question 8

IR of

Anhydrides

Answer 8

~1760 cm-1 AND 1800 cm-1 (two peaks )

Question 9

CNMR of

Benzene carbons

Answer 9

120-150 ppm

Question 10

CNMR of

Carbonyl carbons

Answer 10

190-215

Question 11

CNMR of

Carboxyl carbons
Nitrile carbon

Answer 11

carboxyl = 160-180 ppm

Nitrile = 115-130

Question 12

pKa’s of

Alpha-protons (carboxyl AND carbonyl)

Answer 12

18-20

Question 13

pKa’s of

Benzoic acid
Carboxylic acid

Answer 13

Benzoic = 4

Carboxylic acid = 5

Question 14

pKa PARA to Benzoic Acid of

Nitro
Aldehyde
Halide

Answer 14

Nitro = 3.4 
Aldehyde = 3.8
Halide = 4

(Electron withdrawing groups lower pka)

Question 15

pKa PARA to Benzoic Acid of

H
Methyl
Hydroxyl

Answer 15

H = 4.2 
Methyl = 4.3
Hydroxyl = 4.5 

(Electron donating groups increase pKa)