orgo 2 reactions

2 degree alcohol to ketone

jones or any oxidizing agent

1 degree alcohol to carboxylic acid

strong oxidizing agent

1 degree alcohol to aldehyde

mild oxidizing agent

3 degree alcohol

no reaction

aldehyde to 1 degree alcohol

NaBH4, MeOH or 1) LAH 2) H2O

ketone to 2 degree alcohol

NaBH4, MeOH or 1) LAH 2) H2O

carboxylic acid or ester to 1 degree alcohol

1) LAH 2) H2O

strong oxidizing agents

H2CrO4, KMnO4, jones

mild oxidizing agents

PCC, HOCl via NaOCl with CH3COOH (acetic acid) at 0 degrees

ester to aldehyde

1) DiBAL-H 2) H2O

benzene + HNO3 and H2SO4

benzene + H2SO4

benzene + Br2 and FeBr3 (or AlCl3)

benzene + RCl and AlCl3

benzene + ketone structure with Cl and AlCl3

acid chloride and carboxylic acid with pyridine or TEA

anhydride

acid chloride and alcohol with pyridine or TEA

ester

acid chloride and amine

amide

acid chloride and water

carboxylic acid

anhydride and alcohol

ester

anhydride and amine

amide

anhydride and water

carboxylic acid

carboxylic acid and heat

anhydride

carboxylic acid and alcohol

ester

birch reduction

benzene and Na, NH3, MeOH make diene

polymerization of styrene

styrene and ROOR make chains of styrene

SNAR

benzene with X and KOH, HCl at 70° make benzene with alcohol (replaces X)

strong nucleophilic addition to carbonyl

carbonyl and KOH (aq) make acetal

weak nucleophilic addition to carbonyl

carbonyl and water, HA make acetal

carbonyl with excess alcohol

carbonyl and 2 alcohols make acetal

acetal formation with chained alcohol

carbonyl and chained alcohol makes acetal with o’s connected

imine formation (Shiff base)

carbonyl and primary amine/ammonia make imine

enamine formation

carbonyl with secondary amine/ammonia make enamine

Wolff-Kishner

aldehyde/ketone to imine, imine and KOH, H2O, heat make alkane

acetal back to carbonyl

acetal and water make carbonyl

Wittig reaction

alkane bromine and 1) PPh3 2) BuLi 3) carbonyl make alkene (Z product)

HWE Wittig

alkane bromine and 1) P(OEt)3 2) BuLi 3) carbonyl make alkene (E product)

aldehyde to carboxylic acid (slow)

aldehyde and oxygen make carboxylic acid

aldehyde to carboxylic acid (fast)

aldehyde and Ag2O or KMnO4, KOH make carboxylic acid

benzylic oxidation (alkyl benzene)

alkyl benzene and KMnO4 make benzoic acid

benzylic oxidation (benzyl alcohol)

benzyl alcohol and MnO2 or PCC make benzaldehyde

benzylic bromination

benzene with group attached and NBS or Br2, heat make benzylic bromide

reductive amination

imine and NaBh3CN,[H+] make cyclohexane with amine group

Fischer esterification

benzoic acid and excess alcohol, HA make benzyl ester

cyclic esterification

6 chain carboxylic acid and HA make lactone