ACCA 2

alkene + HX

alkyl halide

alkene + BH3 then H2O2, NaOH

alcohol

acid anhydride + alcohol

ester + carboxylic acid

Alkyne + BH3 then H2O2, NaOH

aldehyde

trans alkene + RCO3H and H2O/H+

trans diol

trans alkene + RCO3H and H2O/OH-

trans diol

trans alkene + KMnO4, OH-/H2O at low temp

cis diol

trans alkene + OsO4, HIO4

two aldehydes

benzene-ketone + Zn/Hg, HCl

alkyl benzene

Benzene + HNO3, H2SO4

Nitrobenzene

Benzene + RCOCl, AlCl3

acyl benzene

synthetic equivalent of R+

RX

secondary alcohol + CrO3, H+

ketone

primary alcohol + CrO3, H+, distillation

aldehyde

primary alcohol + CrO3, H+

carboxyllic acid

aldehyde + CrO3, H+

carboxylic acid

ester + H2O, OH-

alkyl benzene + KMnO4

Benzoic acid

alkene + RCO3H (peracid)

peroxide

trans alkene + OsO4

cis diol

alkene + OsO4, HIO4

ketone + Ph3P=CHR

trisubstituted alkene + Ph3P=O

ketone + NaBH4 then H+

secondary alcohol

aldehye + NaBH4 then H+

primary alcohol

ketone + LiAlH4 then H=

secondary alcohol

aldehyde + LiAlH4 then H=

primary alcohol

amide + LiAlH4 then H+

amine

secondary imine + NaBH4 then H+

secondary amine

Nitrobenzene + Sn, HCl

aniline

alkyne + H2, lindlars catalyst

cis alkene

alkene + H2, Pd/C

alkane

alcohol + PX3

halogenoalkane

carboxylic acid + SOCl2

acyl chloride

acyl chloride + H2O

carboxylic acid

acyl chloride + MeNH2, base

secondary amide

carboxylic acid + ROH, H+

ester

peroxide + H2O, OH- or H2O, H+

1,2 diol

beta bromoalkane + Base

alkene

monosubstituted alkene + HX

halogenoalkane

aminobenzene(aniline) + NaNO2, HCl then H2O, Heat

phenol

grignard + ketone, H+

tertiary alcohol

grignard-benzene + CO2 then H+

benzoic acid

benzene + FeCl3/Cl2

chlorobenzene

grignard + aldehyde, H+

secondary alcohol

grignard + methanal, H+

grignard + epoxide ring, H+

primary alcohol

grignard + CO2

carboxylic acid

2 grignard + ester

tertiary alcohol

benzene + Br2/FeBr3

bromobenzene

benzene + HNO3/ H2SO4

Nitrobenzene

benzene + H2SO4/SO3

benzenesulfonic acid

benzenesulfonic acid + H2SO4, heat

benzene

benzene + RBr/FeBR3

alkylbenzene

benzene + RCOCl/AlCl3

acyl benzene

benzene-MgX + peroxide then H+

2-phenyl ethan-1-ol

bromoalkane + tBuO-

alkene

nitrile + H2O, H+

acyl amide

aminobenzene (aniline) + acyl chloride

phenyl amide

unstabilised ylide forms this type of alkene (E/Z)

Z

stabilised ylide forms this type of alkene (E/Z)

E

terminal alkyne + NaNH2

alkynyl anion

alkyne + Na/NH3

trans alkene

aryl/vinyl halide + monosubstituted alkene (Pd(0) catalyst, base)

disubstituted alkene

methyl ketone + aldehyde, base then H+, heat

alpha beta unsaturated carbonyl

CuI + CH3Li

CH3Cu

CH3Cu + CH3Li

(CH3)2CuLi

aldehyde/ketone + Et3N, Me3Si-Cl

silyl enol ether

silyl enol ether + MeLi

enolate

ketone/aldehyde + pyrrolidine, p-TsOH catalyst

enamine

enamine + HCl

ketone/aldehyde

ester + LDA

enolate

ketone + LDA

enolate

enolate + aldehyde/ketone

1,3-hydroxy carbonyl

R-X + Mg

R-MgX

R-X + 2Liº

R-Li + X+Li-

aminopyridine + NaNO2, HX

halopyridine

positive charge on beta compound

michael acceptor

silyl enol ether + michael acceptor + TiCl4

1,5-dicarbonyl

halopyridine + HNMe2

aminopyridine

pyrrole + NaH, then MeI

N-methyl pyrrole

N-methylated pyrrole + BuLi

2-lithiopyrrole

furan + BuLi

2-lithiofuran

thiophene + BuLi

2-lithiothiophene

to protect an alcohol group:

TBDMS + imidazole

to deprotect an alcohol group

TBAF

to protect a carboxylic acid

MeOH, HCl

to deprotect a carboxylic acid

NaOH then HCl

to protect an aldehyde/ketone

ethane-1,2-diol, p-TsOH

to deprotect an aldehyde/ketone

HCl

to protect an amine

Boc2O

to deprotect an amine

TFA

ketone + RLi or RMgBr then H+

tertiary alcohol

primary alcohol + PCC

aldehyde