X₂ / H⁺ (CH₃COOH) -->

RCOCX

(alpha H replaced with halogen)

X₂ / ^-OH -->

RCOCX

(can replace multiple alpha H's with X)

methyl ketone +

X₂ (excess) / ^-OH -->

carboxylate anion

RCOO^- + HCX₃

(pg 897)

alpha Halo + LiCO₃ / LiBr /

DMF -->

elimination

(halo remove, pi bond formed between alpha and beta C's)

alpha Halo +

nuke (CH₃NH₂) -->

RCOCNu:

(X replaced by NHCH₃)

pg 898

Ketone + LDA /THF -->

enolate at less substituted C

(kinetic enolate)

Ketone +

strong base

(Na^+-OHCH₂CH₃ or

K^+-OC(CH₃)₃)) -->

enolate at more substituted C

(thermo enolate)

LDA

Li^+-N[CH(CH₃)₂]₂