ORGO ALL REACTIONS

birch reduction

Na, NH3, HOR

benzene to bromobenzene

Br2/FeBr3

adding straight chain to benzene

FC acylation, Zn, HCl

adding bulky R groups to benzene

(FC alkylation) RCl, AlCl3

benzene to nitrobenzene

HNO3/H2SO4, H2O

adding SO3H to benzene

fum H2SO4

to remove: dil h2sO4

benzene to iodobenzene

I2/CuI2

benzene to chlorobenzene

Cl2/AlCl3

3 criteria for NAS

• halogen leaving group

• nitro present

• nitro ortho to nucleophile

NAS reagents

NaX, H3O+

elim addition reagents

NaNH2, NH3/ H3O+

toluene to benzoic acid

Na2Cr2O7/ H2SO4, H2O

STRONG R group oxidizer (not t.butyl)

KMnO4, heat/ H3O+

adds Br to benzylic position

Br2, hv

alkene to alkane

H2, Pt/ 2 atm, 25°C

acetal/ketal formation reagents

acetal: H3O+, H2O

ketal: H3O+, ROH

imine form reagents

NH2R, H2O

enamine form reagents

R2NH, H2O

anti markovnikov alkyne ozonolysis

R2BH, H2O2/NaOH

markovnikov alkyne ozonolysis

H2SO4, H2O/HgSO4

primary alc to aldehyde

PCC, ch2cl2

secondary alc to ketone

Na2Cr2O7/H2SO4,H2O

ozonolysis of alkenes

O3/(CH3)2S

witting rxn

Ph3P=R

protecting diol

HOCH2CH2OH, H3O+

removes diol

H3O+/H2O

reduces ketone entirely to alkane

H2N-NH2, KOH, heat

ketone to tertiary alcohol

xs RMgBr/H3O+

ketone/ald. to cyanohydrin

KCN, HCl

CN to amine

LAH, H2O

CN to amide

H2SO4, H2O, heat

amide to carb acid

H3O+, heat

dithiol protecting group

HSCh2CH2SH, TsOH

removes dithiol

H3O+/H2O

dithiol to alkane

H2/ Raney Ni

nBuLi

forms anion from dithiol PG

ester to primary alcohol

LAH, H3O+

ketone + RCO3H

ester

aldehyde to carb acid

na2cr2o7, h2so4, h2o

alkyne to carb acid

O3, H2O

nitrile to amide

H3O+, H2O, heat

amide to carb acid

H3O+, H2O, heat

alkyl halide to carboxylate

Mg/THF, CO2

carboxylate to carb acid

H3O+

carb acid to primary OH (ONLY FOR CARB ACIDS)

BH3/THF

haloform rxn (adding X to all alpha hydrogens)

NaOH, X2

adding X to only one alpha hydrogen

H+/X2

adding Br to most substituted carbon on benzoic acid

Br2, PBr3

enolate forms at less subbed position

LDA, 78° C/ RBr (THERMODYNAMIC)

enolate forms at more subbed position

NaH, 25°C/ RBr (KINETIC)

robinson ring annulation reagents

NaOH, H2O, heat

michael addition reagents

NaOEt (and H3O+, heat for condensation)

stork rxn reagents

enamine/imine, H2O, H+

acid chloride to carb acid

H2O, pyr

acid chloride replaced with R

R2CuLi

acid chloride to tertiary alcohol

xs RMgBr, H2O

acid chloride to aldehyde

LA(OR)3H, H3O+

acid chloride to primary alc

LAH, H3O+

acid chloride to CH3C(O)NHR

xs RNH2

acid chloride to CH3C(O)NR2

xs R2NH

acid chloride to anhydride

carboxylate

acid chloride to ester

ROH, pyr

anhydride to carb acid

h2o

anhydride to tertiary alcohol

xs RMgBr, H3O+

anhydride to ketone

R2CuLi

anhydride to primary alc

xs LAH, H2O

anhydride to acid chloride

SOCl2

anhydride to amide

NH3

anhydride to 2 esters

ROH

anhydride to 2 carb acids

H2O

carb acid to anhydride

NaOH, CH3COCl

ester to carb acid

H3O+, H2O

ester to carboxylate

NaOH, H2O

ester to tert alc

xs RMgBr, H3O+

ester to aldehyde

DIBAH, H3O+

ester to primary alc

LAH, H3O+

ester to amide

NH3

amide to nitrile

SOCl2, -H2O

nitrile to amide

NaOH, heat

amide to amine

LAH, H2O

nitrile to ketone

RMgBr, H3O+

nitrile to primary NH

xs LAH, H2O

ester hydrolysis reagents

H3O+, -ROH

saponification reagents

NaOH, H2O, -OR

aldol condensation reagents

NaOH, H3O+, heat

ammonia to RNH2

R-I

CH3 + RNH2

CH3-NRH

CH3I + R2NH

(CH3)3N

bromobenzene to diazonium

convert bromobenzene to aniline using NaNH2, NH3, H3O+

convert aniline to diazonium using NaNO2, HCl

diazonium to aniline

H2, Pt OR LAH/H2O

gabrielle synthesis reagents

phthalimide, KOH, RBr

phthalimide to carb acids where N leaves

H3O+, H2

phthalimide to carboxylates where N leaves

-OH, H2O

phthalimide to primary NH2

H2N-NH2

alkyl halide to amine

NaNO2/HCl

LAH, H2O

amide/nitrile to amine

LAH, H2O

reductive amination regations

H+, NaBH3CN

alc hoffman elimination

H+, heat, H2O

amine hoffman elimination

xs CH3I

primary amine + NaNO2/HCl

CH3-N≡N