Alcohol reactions

oxymerc-demerc

mark, no rearrangement

acid-catalysed

mark, rearrangement possible, not preferred

hydroboration

anti-mark

syn-hydroxylation

cis-1,2-diol

anti-hydroxylation

trans-1,2-diol

mild reduction of carbonyl

aldehydes and ketones

strong reduction of carbonyl

aldehydes, ketones, acids, and esters

NaBH4

reagent used to reduce a carbonyl, only reduces aldehydes and ketones

LiAlH4/LAH

reagent used to reduce a carbonyl, can reduce aldehydes, ketones, esters, and acids but is very dangerous to use

Grignard reagent

RMgX where R is anything and X is a halide

grignard

primary

grignard

secondary

grignard

tertiary

grignard

grignard

grignard

reduction of an ester

grignard

reduction of an acid

grignard

alkyl halide to alcohol

primary, strong nucleophile

alkyl halide to alcohol

tertiary, weak nucleophile

mild reduction of a carbonyl

mild reduction of a carbonyl

strong reduction of a carbonyl

strong reduction of a carbonyl