carboxylic acids and their derivatives
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85 Terms
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PT, ANp, PT, PT, DNp, PT
- acidic ester hydrolysis
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- acidic amide hydrolysis
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- fischer esterification
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ANp, DNp, PT
- basic ester hydrolysis
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- basic amide hydrolysis
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ANp, PT, DNp, PT
- acid chloride hydrolysis
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- anhydride hydrolysis
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PT, ANp, PT, PT, PT
acidic nitrile hydrolysis
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ANp, PT, PT, PT
basic nitrile hydrolysis
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ANp, DNp, ANp, PT
- ester reduction to a 1º alcohol
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- acid chloride reduction to a 1º alcohol
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- acid chloride with a grignard to get 3º alcohol
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- ester with a grignard to get 3º alcohol
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nucleophile strength of H2O
very weak
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nucleophile strength of ROH
weak
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nucleophile strength of RNH2
moderately weak
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nucleophile strength of OH-, RO-,
moderately strong
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nucleophile strength of LiAlH4, RMgX, RLi
very strong
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carbonyl reactivity scale (strongest to weakest electrophile) from strongest to weakest
1. acid chloride
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2. anhydride
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3. thioester
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4. aldehyde and ketone
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5. carboxylic acid
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6. ester
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7. amine
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8. carboxylic acid conjugate base
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9. amine conjugate base
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acidity trend from most to least acidic
carboxylic acid
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ester
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primary or secondary amide
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tertiary amide
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reagent for diels alder
heat
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acidic ester hydrolysis reagents
H3O+, heat
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acidic ester hydrolysis
ester + water ---> carboxylic acid + alcohol
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basic ester hydrolysis reagents
NaOH/KOH
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basic ester hydrolysis
Ester + water → carboxylate + alcohol
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acidic amide hydrolysis reagents
H3O+, heat
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acidic amide hydrolysis
Amide → carboxylic acid + ammonium ion (NH4+)
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basic amide hydrolysis reagents
OH-, heat
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basic amide hydrolysis
Amide → carboxylate + amine
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acid chloride hydrolysis reagents
H2O (often pyridine if alcohol present)
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acid chloride hydrolysis
Acid chloride + H2O → carboxylic acid + HCl
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anhydride hydrolysis
Anhydride + OH- → 2 carboxylates
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anhydride hydrolysis reagents
OH-
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acidic nitrile hydrolysis
Nitrile → 1º amide → carboxylic acid
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acidic nitrile hydrolysis reagents
H3O+, heat
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basic nitrile hydrolysis
Nitrile → carboxylate
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basic nitrile hydrolysis reagents
OH-, heat
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fischer esterification
Carboxylic acid + alcohol ⇋ ester + H2O
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fischer esterification reagents
H3O+ (acid catalyst)
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esterification via acid chloride
Acid chloride + ROH → ester + HCl
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esterification via acid chloride reagents
alcohol + pyridine
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esterification via anhydride
Anhydride + ROH → ester + carboxylic acid
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esterification via anhydride reagents
ROH, no pyridine necessary
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alkylation of carboxylate
Carboxylate + 1º alkyl halide → ester
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alkylation of carboxylate reagents
1) NaOH (to form carboxylate)
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2) R-X
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amide formation from acid chlorides
Acid chloride + 2 eq. RNH2 → amide + RNH3+Cl-
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amide formation from acid chlorides reagent
2 eq. of RNH2, one equivalent neutralizes HCl
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amide formation from anhydrides
Anhydride + amine → amide + carboxylic acid
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reduction of esters to 1º alcohol
Ester → 1º alcohol + ROH
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reduction of esters to 1º alcohol reagents
LiAlH4, then H3O+
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partial reduction of esters to aldehydes
Ester → aldehyde
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partial reduction of esters to aldehydes reagents
DIBAL-H, -78ºC, then H3O+
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reduction of acid chloride to 1º alcohol
Acid chloride → 1º alcohol
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reduction of acid chloride to 1º alcohol reagents
LiAlH4, then H3O+
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reduction of acid chloride to aldehyde
Acid chloride → aldehyde
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reduction of acid chloride to aldehyde reagent
Li(t-BuO)3AlH
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reduction of carboxylic acid to 1º alcohol
Carboxylic acid → 1º alcohol
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reduction of carboxylic acid to 1º alcohol reagents
LiAlH4, then H3O+
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carboxylic acid selective reduction
Carboxylic acid → 1º alcohol
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carboxylic acid selective reduction reagents
BH3
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reduction of amide to amine
Amide → amine (carbonyl removed)
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reduction of amide to amine reagents
LiAlH4, then H3O+
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reduction of nitrile to 1º amine
Nitrile → 1º amine
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reduction of nitrile to 1º amine reagents
LiAlH4, then H3O+
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acid chloride and grignard reaction
Acid chloride + 2RMgX → 3º alcohol
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acid chloride and gilman reaction
Acid chloride + R2CuLi → ketone
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ester with grignard reaction
Ester + 2RMgX → 3º alcohol
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nitrile and grignard reaction
Nitrile + RMgX → Imine (after attack) + H3O+ → ketone
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tertiary amide and grignard reaction
Addition to give substituted iminium, hydrolysis → carbonyl derivative
Note 
Flashcards (36)