CH3

H3C C

CH3

t-butyl
CH3
H2
H3C C C

CH3

neopentyl
CH3

HC

CH3

isopropyl
CH3
H2
H3 C C C
H

sec-butyl
 CH3
H2
H3 C C C
H

isobutyl

Cyclic Strain

Cyclic Strain

CH3
H CH3

H H
H

gauche

H CH3

CH3
H H
H

eclipsed
H3C CH3

H
H H
H

Totally eclipsed

Oxidation:

PCC
OH

PCC
OH O

OH
Na2Cr2O7
H2SO4

OH O
Na2Cr2O7
H2SO4

OH
KMnO4

OH O
KMnO4

OH
Jones's Reagent

OH O
Jones's Reagent
 OH
[O]

OH O
[O]

OH
Oxidation Reagent

OH O
Oxidation Reagent

OH
Oxidizing Agent

OH O
Oxidizing Agent

Stereochemistry:

R Clockwise

S Counter-Clockwise

Br Br

H H

F Cl Cl F

S R
 Br Br

H H

F Cl Cl F

Carboxylic Group

OH

Formic Acid (Methanoic Acid)

O

HC OH

Acetic Acid (Ethanoic Acid)

H3C C OH

Propanoic Acid
O

H3CH2C C OH

Benzoic Acid

COOH

Carboxylic Acids via Oxidation

KMnO4/OH-
H3O+
OH
 O

KMnO4/OH-
H3O+
OH OH

Carboxylic Acids Via Grignard Reagents

-
RMg+Br CO2

RHC O
-
RMg+Br CO2
-
OMg+Br

RHC O H3O+
-
OMg+Br

O
RHC O H3O+
RC
-
OMg+Br OH

- H3O+
RMg+Br CO2

RHC O
- + H3O+
RMg Br CO2
-
OMg+Br

O
RHC O
- H3O+
RMg+Br CO2 RC
- +
OMg Br OH

Carboxylic Acids Via Alkyl Halides via Nitriles

Esterification (Rxn with COOH)

Decarboxylation (Rxn with COOH)

Acyl Group

Acid Chloride (Acyl Chloride)

Acid Anhydride

Amide
Ester

Nitrile

Acid Derivative

Acyl Halides

Rxns w/Acyl Halides

Oxidation:

PCC
OH

PCC
OH O

OH
Na2Cr2O7
H2SO4

OH O
Na2Cr2O7
H2SO4

OH
KMnO4

OH O
KMnO4

OH
Jones's Reagent
 OH O
Jones's Reagent

Predict the products of the reaction displayed below:

OH
Oxidizing Agent

OH O
Oxidizing Agent

Carboxylic Acids via Oxidation

KMnO4/OH-
H3O+
OH

KMnO4/OH-
H3O+
OH OH

Carboxylic Acids Via Grignard Reagents

-
RMg+Br CO2

RHC O
-
RMg+Br CO2
-
OMg+Br

RHC O H3O+
-
OMg+Br

O
RHC O H3O+
RC
-
OMg+Br OH

- H3O+
RMg+Br CO2
 RHC O
- + H3O+
RMg Br CO2
-
OMg+Br

O
RHC O
- H3O+
RMg+Br CO2 RC
-
OMg+Br OH