Organic Chemistry 2 Reactions

Alkyne + H2 + Pt (PtO2)

Alkane

Alkyne + H2 + Pd-BaSO4 (Pd-CaCO3) + quinoline

Z-Alkene

Alkyne + Na + NH3 + Ethanol

E-Alkene (Birch)

Alkene + H2O + H2SO4

Alcohol (markovnikov)

Alkyne + H2O + H2SO4 + HgSO4

Ketone

Enol

Alkynide Anion properties

Strong Base and Strong Nucleophile

Alkynide Anion + tertiary/secondary alkyl halide

E2 reaction

Alkynide Anion + primary alkyl halide

Sn2 reaction

Strong Bases (x4)

NaH

LDA

Butyl-Lithium

NaNH2

Hemiacetal

Hemiketal

R-Br + Mg + Et2O

R-Mg-Br (grignard)

Ketone/Aldehyde + 1(R-Mg-Br) + 2(Acid)

Alcohol + R

Nitrile + R-Mg-Br

Ketone + R

R-Br + NaCN + EtOH + heat

R-Nitrile

Saturated Ketone + 1(LiAlH4, EtOH) + 2(HCl, H2O)

Alcohol

Unsaturated Ketone + 1(LiAlH4, EtOH) + 2(HCl, H2O)

Alcohol (not conjugated)

Saturated Ketone + NaBH4 + EtOH

Alcohol

Unsaturated Ketone + NaBH4 + EtOH

No Reaction

Ester + 1(excess R-MgBr) + 2(Acid)

Alcohol with 2R

Terminal Alkyne + Strong base

Alkynide Anion

Ketone + Ph3P=R + THF

=R (Wittig)

Ketone + KCN + HCN

Alcohol with CN

Ketone + 1(R-Li2 + Et2O) + 2(H2O)

Alcohol + R

Ester + 1(R-Li2 + Et2O) + 2(H2O)

Alcohol + 2R (alkylithium)

ketone + peroxyacid

(stereochemistry)

Ester (Baeyer-Villiger)

Retain Stereochem

Ketone + H2N-OH + Acid

Amide (C=O, N)

(Beckmann)

Ketone + 1(H2N-NH2 + EtOH) + 2(KOH, heat)

No functional group

(Wolff-Kishner)

Ester + 1(LiAlH4, EtOH) + 2(HCl, H2O)

Alcohol

Amide + 1(LiAlH4, EtOH) + 2(HCl, H2O)

Amine

Carboxylic Acid + 1(LiAlH4, EtOH) + 2(HCl, H2O)

Alcohol

Conjugated Ketone + 1(DIBAL-H) + 2(MeOH)

Alcohol (conjugated)

Ester + 1(DIBAL-H) + 2(MeOH)

2x Alcohol (cleavage)

Will DIBAL-H affect a double bond?

No

Will LAH affect a double bond?

Yes (will react with it in a conjugated ketone)

Nitrile + 1(DIBAL-H) + 2(MeOH) + 3(Acid)

Aldehyde

List the Carboxylic Acid derivatives in order of decreasing reactivity.

Acid chloride, acid anhydride, aldehyde/ketones, ester, amide, carboxylate

Carboxylic acid + SOCl2 (COCl2) + heat

acid chloride

Ester + Acid + H2O

Carboxylic acid + alcohol

Carboxylic acid + alcohol + acid

Ester

Amide + Acid + heat

Carboxylic acid

Nitrile + Acid + H2O

Carboxylic acid

Nitrile + 1(base + H2O) + 2(Acid + H2O

Carboxylic acid

Ester + base

Carboxylic acid

Amide + base

Carboxylic acid

R-MgBr + 1(CO2) + 2(Acid)

Carboxylic acid

Acid chloride + Me2CuLi + Et2O

Ketone + Me

conjugated ketone + LiCu(CH3)2 + THF

Ketone with CH3 added to double bond

Ketone (saturated) + LiCu(CH3)2

No reaction

Ester + LiCu(CH3)2

No reaction

m-CPBA

peroxyacid

Aldehyde + NaBH4 + EtOH

Alcohol

Alkene + KMnO4 + KOH + H2O

Diol (syn)

What will KMnO4 react with first: aldehyde or alkene?

Aldehyde

Me3SiCl + Et3N

TMS-Cl + Et3N

Protecting group for alcohol

TBAF

Deprotection for alcohol

Alcohol + 1(NaH) + 2(R-X)

Ether

(William ether synthesis)

Alkene + H2O + Acid

Alcohol (on more substituted C and possible rearrangement)

Alkene + 1(Hg(OAc)2 + nucleophile) + 2(NaBH4)

Nucleophile on most substituted C and H on less substituted (markovnikov)

(Oxymercuration-demerucuration)

Alkene + 1(BH3-THF) + 2(H2O2, NaOH)

OH on less substituted C and H on more substituted (anti-markovnikov)

(Hydroboration-oxidation)

Alkene + OsO4 + NMO

Syn diol

Primary alcohol + K2Cr2O7 + H2SO4

Carboxylic Acid

(Jones)

Secondary alcohol + K2Cr2O7 + H2SO4

Ketone

(Jones)

Primary alcohol + PCC + CH2Cl2

Aldehyde

Secondary alcohol + PCC + CH2Cl2

Ketone

Primary alcohol + Me2SO

Aldehyde

(Moffatt)

Primary alcohol + (CoCl)2 + Me2SO

Aldehyde

(Swern)

Aldehyde + NaClO2 + CH2Cl2

Carboxylic Acid

(Kraus-Pinnick)

Ether + H-X + heat

X-R + X-R' + H2O

Aromatic Rule

4n+2

Antiaromatic Rule

4n

Alkene + MCPBA

Epoxide

Alkene + 1(Br2, H2O) + 2(NaOH)

Epoxide

Epoxide + basic nucleophile + H2O

Opening

(Inverts stereochemistry)

(Nucleophile attacks less substituted C)

Epoxide + Acid

Opening

(Retains stereochemistry)

(Nucleophile attacks more substituted C)

Alcohol + TsCl + Py

Sulfonate Ester (R-O-Ts)

(good leaving group)

Alkene + 1(O3) + 2(DMS)

Ozonolysis (double bond becomes two Carbonyl groups)

Diol + HIO4

Cleavage and formation of two carbonyl groups

Alkene + OsO4 + NaIO4 + H2O/Acetone

Cleavage and formation of two carbonyl groups

(Lemieux-Johnson)

Ketone/Aldehyde + Enolate

Addition

(Carbonyl attack carbonyl)

(a ketone from the enolate is also formed)