chem 51b reagents

NaNH2 or NaH

strong base, reacts in excess to form acetylene

(1) BH3, THF (2) H2O2, NaOH

hydroboration-oxidation, adds OH to less substituted side

H-X

Hydrohalogenation (Markovnikov)

Br2

halogenation, anti

H2SO4, H2O

hydration (attack from pi bond) Add H+OH Markov. mix of syn and anti addition due to carbocation, E1

TsCl, pyridine

Substitutes OH with OTos with retention of configuration. OTs is a good LG

Syn.

KOC(CH3)3

strong base, weak nucleophile as bulky

Br2, H2O

bromohydration

H2SO4 (conc)

Dehydration; alcohol to alkene

H-X addition

alkyl halide formation syn and anti due to carbocation

SOCl2, pyridine

replace OH (primary or secondary) with Cl, inversion by SN2

PBr3, pyridine

replace OH (primary or secondary) with Br, inversion by SN2

(1. Br2, H2O 2. NaH) or mCPBA

alkene —> epoxide (racemic)

H2, Lindlar's catalyst

add H2 to alkyne —> cis alkene

NaOEt, EtOH

E2, requires a good leaving group

LiAlH4

reducing agent, R-X —> R-H by SN2

H2, Pd-C

hydrogenation of alkynes —> alkenes —> alkanes by syn addition

NaNH3

add H2, alkyne to trans alkene

NBS, ROOR, hv

adds Br to allylic C

HBR, ROOR, hv

adds Br to least substitute alkene carbon

Br2, hv

alkane to bromyl halide, adds to most substituted carbon

KMnO4, NaOH, H2O

syn dihydroxylation of alkene

PCC

oxidizes primary alcohols to aldehydes

1) O3 2) (CH3)2S

ozonolysis of alkene into two ketones

CrO3, H2SO4

1° alcohol to carboxylic acid

and 2° alcohol to ketone

1) O3 2) H2O

ozonolysis of alkyne into carboxylic acid

NaOH

SN2 (change X to OH)

LiAlH4, H2O

epoxide opening to alcohol, H adds on least substituted side

9-BBN

hydroboration (for alkynes instead of BH3,THF)