Alcohols Lecture-2
Alcohols
Olefins
vicinal $(1,2$-diol $)$
Monohydric alcohols
Dihydric alcohols
oxidation
$\mathrm{KMnO}_4$ aq cold. alkaline
$\mathrm{OSO}_4 / \text { peroxide / } \mathrm{OH} \text { - }$
Reaction
Per acid oxidation
Structure
Reducing agents: a) Hâ‚‚/Ni or Pd : hydrogenation
: Na/alcohol (esters $\rightarrow$ alcohol)
Bouveault-blanc reduction.
: c) Alisopropoxide / isopropanol
MPV (Meerwein Ponndorf verley reduction)
Mixed metal hydrides
$LiAlH_4$
$NaBH_4$
reactivities
selectivity
stronger
mare reactive
less selective
acid chloride, aldehyde,
ketone, ester, amide, acid,
$Li^+$ small cation
coordinates >c=o oxygen
increasing elechophilicity of >= 0
stronger Lewis acid
Al ~ 15
B more electronegativity than Al
B - H $\rightarrow$ $H^-$
weaker reducing agent
(3) Al > B size
AlH $\hspace{15mm}$ BH
$3sp^2 - 1s$ $\hspace{5mm}$ $2sp^3 - 1s$
Al - H $\hspace{14mm}$ B - H
longer $\hspace{13mm}$ shorter
weaker $\hspace{12mm}$ stronger
more reactive $\hspace{5mm}$ less reactive diffuse
$NaBh_4$ ?
NaH
cannot be used as nucleophile
Good base
NaH is orbital is too small to interact well with $\hspace{5mm}$ >=o c
Mechanism
$NaBH_4$: water soluble, tetrahedral $BH_4$ anion
Chemeoselective
C-C bond formation
Thank you