MCAT Redox

1* Alcohol (reducing agent) + PCC or CrO2/pyrimidine(oxidizing agent)

aldehyde

2* alcohol + PCC or CrO2/pyrimidine(oxidizing agent)

ketone

aldehyde + H2CrO4/KMnO4/H2O2

Carboxylic acid

alcohol + KMnO4/H2Cr2O4

carboxylic acid

benzylic alkane + KMnO4

carboxylic acid

alkene can be cleaved by O3/Zn to form

aldehyde or ketone

alkene can be cleaved by O3/H202 to form

ketone/carboxylic acid

alkyne + O3/H2O2

carboxylic acid

alkene + OsO4 or KnMnO4, -OH

diol

alkene + mCPBA

epoxide

diol + NaIO4

aldehyde

ketone + mCPBA

ester

aldehyde + LiAlH4 (reducing agent)

1* alcohol

Ketone + LiAlH4

2* a;cohol

amide + 1. LiAlH4, 2. H+

primary amine

carboxylic acid 1. LiAlH4, 2. H2O

primary alcohol

ester + 1. LiAlH4, 2. H2O

primary alcohol

How is an alcohol oxidized to an aldehyde?

PCC (anhydrous)

Jones oxidation

reaction of primary alcohol to carboxylic acid

Reagents necessary for 1* Alcohol→ Carboxylic acid

CrO3( super strong oxidant), h2so4, acetone

mesylate

Formation of mesylate requires

methylsulfonyl chloride + alcohol + base

tosylate

how to form a tosylate

toulene sulfonyl chloride + alcohol

Role of mesyl and tosyl groups

make alcohol a good LG

protect alcohols

quinones

how are quinones formed

oxidation

of benzenediol

ubiquinone

biologically active quinone (Coenzyme Q)

electron carrier