Unit 2 Reactions

Hydroboration Oxidation

1. BH3 2. NaOH, H2O2, less substituted anti markovnikov, OH to alkene

Oxymercuration-Demercuration

1. Hg(OAc)2, H2O 2. NaBH4, most substituted markovkinov, OH to alkene

Dihydroxylation

1. OsO4 2, NaHSo3, H2O, Adds double OH OH, syn

Selective Ketone Reduction

1. NaBH4, H3O+, 2 carbonyls and one becomes OH or single ketone

Complete Ketone Reduction

1. LiAlH4, H3O+, carbonyl gone

Grignard Reagent

1. R-MgBr, H3O+, Attaching carbon group to carbonyl

Dehydration of Alcohols

1. POCl3, pyridine, Alcohol to alkene

Oxidation of Alcohol

1. CrO3, H3O+, alcohol to carbonyll

Dess Martin Oxidation

1. DMP, CH2Cl2, Alcohol to carbonyl

Acidic workup of tertiary alchohol

1. H2SO4 or 1. H30+, eliminates alcohol to form alkene

Tertiary alcohol to alkyl halides

1. HCl or 2. HBr

Side chain Carboxylic acid

1. KMn04, H2O

Symmetrical Ethers

1.H2SO4, primary alcohol

Williamson Ether Synthesis

1. NaH, THF 2. CH3-I, alcohol to ether

Oxymercuration

1. Hg(OAc)2, CH3OH 2. NaBH4 (remove HgOac), alkene to ether

Acidic Cleavage of ether

1. HBr, Ether to alkene

Epoxide opening

1. H3O+ , double OH

Epoxide formation

1. MCPBA, alkene to epoxide

Epoxide opening with acid halide

1. HCl, Ether, adds alcohol and Cl

Basic ring opening

1. OH, H2O 100C 2. H2O, double OH or 1. NaOh, H2O

Oxidation of primary alcohol

1. PCC, CH2Cl2, alcohol to aldehyde

Ozonolysis of alkenes

1. O3 2. DMS, Cleave C=C bond to aldehyde or ketone

Hydroboration-Oxidation of Terminal Alkynes

1. R2B-H 2. H2O2, NaOH, alkyne to aldehyde and can enol to alcohol

Oxidation of secondary alcohols

1. Na2Cr2O7, H2SO4, H2O, alcohol to ketone

Acid Catalyzed Hydration of Terminal Alkynes

1. H2SO4, H2O, HgSO4, ketone

Friedel Crafts Acylation

1. R-Cl, AlCl3, add group onto benzene

Hydrogen Nucleophile

1. LialH4 2. Dilute HCl, ketne to primary alcohol

Wittig Reaction

1. Ph3P=CH2, add CH2 to alkene

Baeyer Villager Oxidation

1. RCO3H or MCPBA, ketone to ester

Cyanohydrin formation

1. CN, ketone to CN + OH

Gilman Reaction

1. R2CuLi 2. H3O+, Add R group to alkene with aldehyde

Ozoneanalysis

1. O3 2. Zn/H3O+ , side chain alkene gets cleaved to into Ketone and COH2

Enamine formation

1. RNRH

Imine formation

1. RNH2

Reversing imine

1. HA

Acetal Formation

1. 2CH3OH, HCl catalyst, on cyclohexane with ketone adds 2 O -R groups

Wolf Kishner Reduction

1. H2NNH2, KOH, removes carbonyl side chain