organic chemistry exam 1

Ether

Alkane

C - C

pKa 50

Alkene

C 2- C

Alkyne

C 3- C

pKa 25 when R - C 3- C - H

Alcohol

C - OH, pKa 16

Thiol

C - SH

Amine

|
R - N
|

pKa 35, protonated (+ on N) pKa 10

Peroxide

R - O - O - R

Epoxide

O
C - C

Aryl

a 6 carbon bond with 3 alkenes and an R group attached

pKa 40

Phenol

A 6 carbon ring with 3 alkenes and a hydroxide attached

pKa 10

Aldehyde

H
|
O 2- C

Ketone

O
2-
C - C - C

Carboxylic Acid

O
2-
R - C - OH pKa 5

Ester

|
O 2- C - O -

Acid Chloride

O
2-
- C - Cl

Amide

O
2- |
- C - N
|

pKa 15

Anhydride

O O
2- 2-
- C - O - C -

Peracid

O
2-
- C - O - O - H

Nitrile

- C 3- N

IR: O - H, N - H, sp/sp2 C-H

4000-3000

IR: sp3 C-H

3000-2500

IR: C 3- C, C 3- N

2500-2000

IR: C 2- C, C 2- O, C 2- N

2000-1500

Water

H2O
pKa 16

Carbonyl

O 2- C
|
R

next to carbonyl pKa 20, between two carbonyls pKa 10, protonated (+ on O) -7

Hydronium

H3O

pKa 0

pKa phenol

10

pKa aryl

40

pKa: protonated carbonyl (+ on O)

-7

pKa: H adjacent to carbonyl (on C)

20

pKa: H between two carbonyls

10

pKa: protonated hydronium, alcohol, or ether

0

pKa: carboxylic acid

5

pKa: amine (H on N)

35

pKa: protonated amine (H on N)

10

pKa: alcohol

16

pKa: water

16

pKa: terminal alkyne (R - C 3- C - H)

25

pKa: amide (H on N)

15

pKa: alkane

50

pKa: HCl

-7

pKa: HI

-10