alcohol---> alkyl halide
HX
alcohol---> alkene
H+ and heat
alkane--->alkyl halide
X2 and heat (radical)
alkane--->alkyne (double dehydrohalogenation)
2 equiv. NaNH2
alkene--->alkane
H2 and Pt (syn)
alkene--->dihalogenated product
X2 and inert solvent ie: CHCl3 (anti)
alkene--->alcohol (hydration)
H2O and H+ (Markovnikov)
alkene--->alcohol (hydroboration oxidation)
1.BH3, THF 2. H2O2, OH-, H2O (anti-markovnikov)
alkene--->alkyl halide
HX (regioselective) (markovnikov)
alkene--->alkyl halide (anti Markovnikov)
HBr, ROOR, heat
alkene--->halohydrin/haloether
X2,H2O or X2,ROH (OH/RO to most subbed carbon)
alkene--->epoxide
RCOOOH (concerted syn addition)
alkene---> aldehyde/ketone
(ozonolysis) 1. O3, -78C
2. Zn, DMS
alkyl halide--->alkene
base, heat
bulky base such as TBuOH favors minor product
alkyne--->alkane
2 equiv. H2, Pt,Ni,Rh,Pd
alkyne--->alkene (cis)
H2, Lindlar Pb
alkyne-->alkene (trans)
Na, NH3
alkyne--> alkyl halide
2 equiv. HX
Halogenation of alkynes
2 equiv. X2
alkyne--->ketone
H2O, Hg2+, H3O+ (hydration) (forms via keto-enol tautermization)
terminal alkyne--->aldehyde
1. R2BH 2. H2O2,NaOH (hydroboration)
alkyne--->carboxylic acid
1.O3 2. H2O (internal alkyne forms 2 carboxylic acids = to total carbons in original chain, terminal alkyne forms 1 carboxylic acid w/ less carbon than original chain +CO2 and H2O)
Diels Alder
Diene +Dienophile @ 200C (cyclic+acyclic = bicylcic, acyclic+acyclic = cyclic)
Birch Reduction
Na,NH3,ROH (makes benzene non-aromatic)
oxidation of benzene
NaCr2O7, H2SO4, heat (occurs at benzylic C)
halogenation of benzene
X2, FeX3 (free radical) or NBS,CCl4, benzoyl peroxide @80C
nitration of benzene
HONO2, H2SO4 @30-40C
sulfonation of benzene
HOSO2OH, heat (only reversible substitution)
friedel-krafts acylation
RCOCl, AlCl3 (forms a C-C) bond
friedel-krafts alkylation
AlCl3,RCCl @ 0C (forms C-C) bond