All Orgo Reactions for Exam 3

Aldehyde/ketone + H₃O⁺ or OH⁻

diol (hydrate)

Aldehyde/ketone + ⁻C≡N

cyanohydrin

Aldehyde/ketone + amine

imine

Aldehyde/ketone + alcohol

acetal

Aldehyde/ketone + diol

cyclic acetal

Aldehyde/ketone + Ph₃P⁺CH–R

alkene + Ph₃P=O

Acid chloride + AlCl₃

Friedel–Crafts acylation → ketone

Acid chloride + R₂CuLi

ketone

Acid chloride + AlH(O-t-Bu)₂

aldehyde

Acid chloride + amine + H⁺

amide

Acid chloride + alcohol

ester

Carboxyl + SOCl₂

acid chloride

Carboxyl + alcohol + H⁺

ester

Carboxyl + CH₂N₂

ester

Carboxyl + amine → salt + protonated amine → _____

amide

Carboxyl + LiAlH₄

primary alcohol

Carboxyl + BH₃/THF

primary alcohol

Carboxyl + LiOH

ketone

Alkyne + Hg²⁺ + H₂SO₄

ketone

Alkyne + Sia₂BH

aldehyde

Nitrile + Grignard/organolithium

ketone

Nitrile + (i-Bu)₂AlH

aldehyde

Ester + DIBAL

aldehyde

Amine + alkyl halide

more substituted amine

Amine + 3 CH₃–I + Ag₂O

Hofmann elimination → alkene + amine

CO₂ + Grignard

carboxylate

Nitrile + H₂O

carboxyl

PCC

1° alcohol → aldehyde; 2° alcohol → ketone

Na₂Cr₂O₇

1° alcohol & aldehydes → COOH; 2° alcohol → ketone; benzylic carbon → COOH

Cold KMnO₄

alkenes → syn diol

Hot KMnO₄

1° alcohol & aldehydes → COOH; 2° alcohol → ketone; benzylic carbon → COOH; alkenes → cleavage + full oxidation

O₃

alkenes → cleavage

Ag₂O

R–N(CH₃)₃⁺I⁻ → R–N(CH₃)₃ + OH + AgI

2 Ag(NH₃)₂OH

aldehyde → carboxylate

Br₂

aldehyde → COOH

HNO₃

aldehyde & 1° alcohol → COOH

NaOCl

1° alcohol w/TEMPO → aldehyde; 1° alcohol → COOH; 2° alcohol → ketone

Zn(Hg) / HCl

Clemmensen reduction → full reduction (remove all oxygen)

NaBH₄

aldehyde → 1° OH; ketone → 2° OH

LiAlH₄

aldehydes, COOH, esters, acid chlorides → 1° OH; ketones → 2° OH; amides & nitriles → amines

NaBH₃CN

iminium salt → amines; aldehydes → 1° OH

Catalytic hydrogenation

alkenes & alkynes → alkanes; aldehydes → 1° OH; ketones → 2° OH; imines & nitriles → amines

DIBAL-H

esters, nitriles, acid chlorides → aldehydes

(t-BuO)₃AlH

acid chlorides → aldehydes

BH₃/THF

COOH → 1° OH

(i-Bu)₂AlH

nitriles & acid chlorides → aldehydes

Acid amino acid Isoelectric point calculation

(pK1 + R)/2

Basic amino acid Isoelectric point calculation

(pK2 + R)/2

Carboxyl + Br2/PBr3 + NH3

amino acid synthesis

Aldehyde + NH3 + HCN

amino acid synthesis

Protecting a carboxyl group uses an ____ and forms an ____

alcohol; ester

Protecting an amine group uses an ____ and forms an ____

acid chloride; amide

Two cysteine residues in a peptide bond to form a ____

disulfide bond

Erythro

substituents on same side (symmetrical/meso)

Threo

substituents on different sides (asymmetrical)

Epimers

Carbohydrates that differ in stereochemistry at ONLY ONE carbon

Alpha glycosidic linkage

Anomeric carbon and CH2OH are trans to each other and anomeric carbon binds to another sugar

Beta glycosidic linkage

Anomeric carbon and CH2OH are cis to each other and anomeric carbon binds to another sugar

sugar + CH3I + Ag2O

alcohol → ether

sugar + anhydride w/ pyridine

alcohol → ester

sugar + Br2 + H2O2 w/ Fe2(SO4)3

shorten a sugar

sugar + HCN + H2Pd + H3O

lengthen a sugar