Reactions of acid chlorides

acid chlorides are ___ version of carboxylic acid and are ___

activated version of cooh
highly reactive electrophiles (things that get added to)

general reaction

acid chloride with weak nu and base to r-conu

reactions usually addn/elim

what bases? and what do they do?

NaHCO3, Na2CO3, Pyridine, Et3N

base neutralizes any acid side products

acid chlorides are often used to …

synthesize other acid derivatives

acid chloride to other acid derivatives usually occur thru…

addn/elim

acid chloride to carboxylic acid

hydrolysis
H2O and Na2CO3

acid chloride to ester

REVIEW RXN

ester formation, reactions of alcohols

R-OH and Et3N

acid chlorid to anhydrides

NEW!! Synthesis of anhydrides

r-cooh and Na2CO3 (any base)

acid chloride to acetophenone vibes (phenyl + ketone with R group)

Freidel-crafts acylation (REVIEW)* not addn/elim

benzene and AlCl3 catalyst

acid chloride to alcohol (not often used)

REVIEW addn/elim

cuz extremely exothermic and possibly dangerous

1) 2 eq of R-MgBr or organolithium reagents
2) acid water work up

acid chloride to ketone

REVIEW addn/elim

(R)2CuLi (organocuprate, weaker Nu:)

acid chloride to aldehyde

REVIEW reduction! from synthesis of aldehyde and ketones

1) LiAlH(Otbu)3 vs DIBAL-H (Diisobutylaluminum hydride)
2) acid water workup

acid chloride to alcohol

REVIEW reduction via addn/elim from synthesis of alcohols
1) LiAlH4 (not often used extremely exothermic) or NaBH4 (acid chloride very reactive NaBH4 is preferred reducing agent)
2) acid waterworkup

acid chloride to aldehyde** (no mechanism)

Rosenmund reduction (review)

H2, Pd/BaSO4 (poision catalyst), S and Et2O