Chem U1 (not on sheet reactions)

alcohol —> alkene

H2SO4, heat (make into good LG by protonating, then do elimination)

—> water as LG, water will leave, create carbocation and the H bonds will go to the carbocation (more substituted one, less Hs — mark) — look out for shifts

alkyl halide —> alcohol

NaOH

typical substitution reaction with OH as the nucleophile

** carbonyl —> alcohol c=o —> c-oh

1)LiAlH4 | 2) H3O+

—Br + carbonyl/epoxide—> alcohol

Mg, Et2O & H3O+ acid workup

alcohol —> ether

1) NaH | 2) alkyl halide

alkene —> alkyl halide (addition)

HBr (markovnikov), HBr | ROOR, heat (anti markovnikov)

alkane —> alkyl halide

Br2 | hv, heat (radical bromination) - forms good lg

alkene —> anti dihalide (to X groups) — addition

X2 | Ch2Cl2

**alcohol —> carbonyl

PCC | CH2Cl2 (mild, keep aldehydes), CrO3 | H2SO4 (strong, carboxylic)

carboxylic acid + alcohol —> ester

H2SO4, heat —> Fischer esterification

alkyne —> carbonyl (2 ways)

(add to more substituted side c=o)

HgSO4 | H2SO4, H2O (acidic conditions, enos will attack acid with DB first, cation)

(add to less substituted side c=o)

1) Sia2BH | 2) H2O2, NaOH, H2O

tautomerization of enol

alkyne —> alkene

H2/Lindlars —> cis

1) Na, NH3 | 2) H3O+ —> trans

ether —> cleaved ether

2eq HBr (or HX, essentially it’s gonna become OH, better LG, Br will attack a adj carbon)

• think of it like a strong acid attacking an epoxide

Protecting alcohols

TIPSCl, Et3N | n-Bu4N+F/THF

halohydrin / alkene —> epoxide

1) Br2, H2O | 2) Et3N

reactions of epoxides (describe 2 kinds)

1) ring opening under acidic conditions — form OH LG, similar to ring opening of ether

2) ring opening with strong nucleophiles (NaOH | H2O) common

— can occur with any strong nucleophile, like Grignard or Acetylide