Nucleophilic Elimination + Addition
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28 Terms
Acid chloride (position on ladder)
Rung 5 (top)
Acid anhydride (position on ladder)
Rung 4
Ester (position on ladder)
Rung 3
Carboxylic acid (position on ladder)
Rung 3
Amide (position on ladder)
Rung 2
Carboxylate anion (position on ladder)
Rung 1 (bottom)
Acylation reagents
Acid chloride or acid anhydride + Nu
Trans-esterification reagents
Ester + good Nu
Saponification reagents
Ester or amide + OH- and H2O
Saponification products (with ester)
Carboxylate anion + alcohol
Saponification products (with amide)
Carboxylate anion + amine
Products with organometallics reagent
Alcohol + 2 R groups
Acid chloride + NaBH4
Primary alcohol
Acid anhydride + NaBH4
Primary alcohol + carboxylic acid
Ester + NaBH4
USUALLY NO RXN; 2 different primary alcohols
Carboxylic acid + NaBH4
NO RXN
Amide + NaBH4
NO RXN
Acid chloride + LiAlH4
Primary alcohol
Acid anhydride + LiAlH4
2 identical primary alcohols
Ester + LiAlH4
2 different primary alcohols
Carboxylic acid + LiAlH4
Primary alcohol
Amide + LiAlH4
Amine
Acid chloride + LiAlH(Ot-Bu)3 product
Aldehyde
Acid chloride + (CH3)2CuLi products
Ketone
Gabriel synthesis reagents
1. primary or secondary halide, potassium phthalimide, DMF; 2. KOH, H2O and heat
Gabriel synthesis product
Amine +
Haloform reaction reagents
Methyl ketone, NaOH, X2 then acid
Haloform reaction products
Carboxylic acid and haloform (HCX3)