CHE 118C UC Davis

An alcohol to an Ester

An anhydride with base, then acid work-up

Carboxylic acid to COOH w/alpha X

Br2, trace P

COOH to Primary Alcohol

Strong reducing agent, then acid work-up

COOH to Amide

NH3, DCC

COOH to Ester

ROH, acid, and heat

COOH to Anhydride

Heat

Primary Alcohol to RX

PX3, base like pyridine

Benzene with Chain to Benzene with COOH

1) KMnO4, H2O, heat

2) Acid work-up

RX to RCOOH

1) NaCN, base

2) acid work-up

Nitrile to COO- + NH3

H2O, base, heat

Nitrile to Primary Amine

1) Strong reducing agent

2) Acid work-up

Nitrile to Adelhyde

1) DIBAL

2) Acid work-up

Nitrile to Ketone

1) R'MgX

2) Acid work-up

Nitrile to COOH and NH4+

H2O, acid, heat

Amide to Nitrile

PX3

Primary Amide to Primary Amine

Br2, base, water

Cyclic Tertiary Amide to Cyclic Tertiary Amine

1) reducing agent

2) acid work-up

Tertiary Amide to Aldehyde

1) DIBAL

2) acid work-up

Amide to RCOO- and NH3

H2O, base, heat

Amide to RCOOH and NH4+

H2O, acid, heat

Ester to Amide with 1 less H

not primary amino group

Ester to Aldehyde

1) DIBAL

2) acid work-up

Ester to Symmetrical, Alkylated Alcohol

R"Li and water

Ester to Ester with Alpha R'

1) LDA

2) R'X

X

X

Cyclic Ester to Open-Ring Ester and Alcohol

Alcohol and hot acid

XX

XX

Ester to COO- and ROH

H2O, base, and heat

Ester to COOH and ROH

H2O, acid, and heat

Acyl Halide to Ester

ROH with base like pyridine

XXX

XXX

Ketone to Ester

Peroxide

Acyl Halide to Symmetrical, Alkylated Alcohol

1) R'MgX

2) acid work-up

Acyl Halide to Ketone

R'2CuLi

Acyl Halide to Aldehyde

1) DIBAL

2) acid work-up

Acyl Halide to Primary Alcohol

1) reducing agent

2) acid work-up

Acyl Halide to Amide

at least a primary amino group

XXXX

XXXX

Acyl Halide to Anhydride

RCOOH and base like pyridine

Acyl Halide to COOH

H2O and base like pyridine

At least Primary Amine to Amine w/another Methyl and Alkene that Came Off that Would be the Least Substituted

1) CH3I

2) Ag2O, water, heat

Benzyl Azide to Benzyl Nitrile

CuCN

Benzyl Azide to Benzyl Bromide

CuBr

Benzyl Azide to Benzyl Chloride

KCl

Benzyl Azide to Benzyl Fluroide

HBF4

Benzyl Azide to Phenol

H2O, acid, heat

Benzyl Azide to Benzyl Iodine

CuI

Benzyl Azide to Benzene

H3PO2

Benzyl Amine to Benzyl Azide

NaNO2, acid, cold

Amide to Amine

1) Reducing agent

2) acid work-up

Ketone/Aldehyde to 2/1 Amine

1) 1/0 Amino group

2) NaBH3CN, water

Secondary Amine and NaBH3CN, acid, cold

R2-N-N=O

Gabriel Synthesis

1) NaOR, ROH

2) RX

3) water, base, heat

RX to Amine

RX and

1) NaN3

2) Reducing agent

3) acid work-up

Ketone/Aldehyde to Tertiary Amine

Ketone/Aldehyde and

1) 2 amino group

2) NaBH3CN

Benzene w/X and EWG to Phenol w/EWG

Benzene w/X and EWG and

NaOH and water

Tertiary Amine to Tertiary Amine

Tertiary Amine and

NaNO2, acid, cold

RX to Primary Amine with New C

RX and

1) NaCN

2) reducing agent

3) H3O+

Ketone and Aldehyde to Alpha Addition

Ketone and Aldehyde and

1) Amine, acid, heat

2) base, water

XXXXX

XXXXX

Primary Amine to R-Nu

Primary Amine and

1) NaNO2, acid, cold

2) a Nu

Benzyl Amine to Phenol

Benzyl Amine and

1) NaNO2, acid, cold

2) hot water

Double Phenol to Double Cyclic Ketone

Double Phenol and

Jones

Phenol to Bakelite Polymer

Phenol

Formaldehyde and base

Benzylic -OH on a Chain to Ketone

Benzylic -OH on a chain and

MnO2

Phenol to Benzene w/Ester

Phenol and

Acyl halide

Benzene w/an Ethyl (or +) chain to Benzene w/a Ketone

Benzene w/an Ethyl (or +) chain and

Jones

Benzene w/a Methyl chain to Benzene w/a COOH

Benzene w/a Methyl chain

Jones

Phenol to Phenol w/Ortho or Para X

Phenol and

Br2, CH3Cl, cold

Benzene w/X to Phenol

Benzene w/X and

1) NaOH, heat, pressure

2) acid work-up

Benzene w/Ether chain to Benzene w/Chain up til where the O was

Benzene w/Ether chain

H2, Pd-C

Benzene w/chain to Benzene w/COOHs

Benezene w/chain

1) KMnO4, hot water

2) acid work-up

Phenol to Phenol w/all ortho and para X's

Phenol and

Br2 and water

Double Phenol to Double Phenol w/Cl on side

Double Phenol and

1) Jones

2) HCl

Phenol to Phenol w/Alkene chain ortho to -OH

Phenol and

1) NaOH, heat

2) Alkene with X