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acyl chloride + H2O → ?
carboxylic acid (hydrolysis)


Acid chloride + ROH → ?
Ester + HCl

Acid chloride + NH₃ or amine → ?
Amide + HCl.

Acyl chloride + R₂CuLi (Gilman reagent)→ ?
Ketone


Acyl chloride + RMgBr (Grignard reagent)→ ?
Tertiary alcohol after hydrolysis.

Reagent that converts carboxylic acid to acid chloride?
SOCl₂ + Base
Anhydride + water → ?
2 carboxylic acids.
Anhydride + ROH → ?
Ester + carboxylic acid.
Anhydride + amine → ?
Amide + carboxylic acid.
Ester + H₂O / acid or base → ?
Carboxylic acid + alcohol (hydrolysis).
Ester + NH₃ → ?
Amide + alcohol.
Ester + LiAlH₄ → ?
Primary alcohol (reduction).
Ester + RMgBr → ?
Tertiary alcohol (2 additions).
Amide + LiAlH₄ → ?
Amine (reduction).
Amide + water + heat (acid/base) → ?
Carboxylic acid (hydrolysis).

Nitrile + LiAlH₄ → ?
Primary amine.


Nitrile + H₂O + heat → ?
Carboxylic acid.


ketone + (1)NaBH₄, (2)H+ → ?
secondary alcohol

(Aldehydes, ketones, esters, acids, amides, epoxides and nitriles) + (1)LiAlH₄ , (2)H+→ ?
alcohols or amines.

What does PCC oxidize a primary alcohol to?
Aldehyde.


What does Jones reagent oxidize a primary alcohol to?
Carboxylic acid.


Aldehyde or ketone + Grignard reagent → ?
Alcohol (1°, 2°, or 3° depending on structure).


Aldol condensation product after dehydration?
α,β-hydroxy dicarbonyl


What does Claisen condensation form?
β-keto ester or β-diketone.


Aldehyde or ketone + 2ROH + acid → ?
Acetal (protecting group).


Acetal + H2O + ROH → ?
aldehyde or ketone

What does Jones reagent oxidize a secondary alcohol to?
Ketone

Aldehyde + (1)NaBH₄, (2)H+ → ?
primary alcohol


Diels Alders + cis alkene
meso compound


Diels alder + trans alkene
enantiomers


Nitration rxn
note* this rxn has sigma complexes


Sulfonylation rxn
note* this rxn has sigma complexes


Carbonyl + primary amine
imine


carbonyl + secondary amine
enamine


amide + H3O+ + heat
Carbo. acid + amine


Ester hydrolysis: base catalyzed
carbo. acid + acid


Ester hydrolysis: acid catalyzed
carbo. acid + acid


Electrophilic Aromatic Substitution rxn
note* this rxn has sigma complexes


Bromination(chlorination) EAS rxn
note* this rxn has sigma complexes


Activating (EDG) disubstitution
2 products: ortho and para


Deactivating (EWG) disubstitution
1 product: meta


Decarboxylation rxn


Esterification rxn


Carbanion addition


Sn2 - alkylations


cbz protection


Boc protection


carboxylic acid + ROH + H+ (Fischer esterification)
Ester + H2O
