Organic Chemistry ACS final

alkene to alkyl halide

HX

Adds H and X

Mark.

alkyl halide to alkene

KOH

elimination

alkene to alcohol (MARK)

H20, H3PO4, heat

adds OH and H

Mark.

Hg(OAC)2, H20, NaBH4

adds OH and H

Mark.

alcohol to alkene

H2SO4, H2O, THF, heat

alkene to alcohol (Non-Mark.)

BH3, THF, H2O, OH-

alkene to 1,2-dihalide

X2

adds X and X ANTI

alkene to halohydrin (Br)

NBS, H2O, DMSO

adds OH/BR anti-mark

ANTI

alkene to halohydrin

X2

H2O

Adds OH/X

ANTI

alkene to alkane

H2, Pd, Pt, Ni

Adds H/H

SYN

alkene to epoxide

mCPBA, CH2Cl2

epoxide to 1,2-diol

H+, H2O

alkene to syn 1-2 diol

OsO4, NaHSO3, H2O

SYN

alkene to 2 carbonyls

O3, CHCl2, Zn, H3O+, or Me2S

alkene to carbonyl

KMnO4, H3O+

carbonyl + CO2 are products

syn 1,2-diol to carbonyl

HIO4, THF, H2O

alkene to epoxide to anti 1,2, diol

mCPBA, CH2Cl2 and H3O+/heat

1,2-dihalide to alkyne

2KOH, ethanol

trans vinyl halide to alkyne

KOH, ethanol

alkyne to X,X halide

2 HX/CH3CO2H

alkyne to tetrahalide

2 X2/CH2Cl

alkyne to carbonyl (2)

H2O, H2SO4, HgSO4

OR

BH3, THF, H2O2,OH-

alkyne to alkane

2 H2/Pd,Pt,Ni

alkyne to cis alkane

H2, lindlars

alkyne to trans alkene

2 Li/NH3(l)

alkyne to acid

KMnO4

alkyne to alkylation

NaNH2,NH3(l) and CH2CH3X

alcohol to alkyl halide (general)

HX/heat

alcohol to alkyl chloride

SOCl2, pyradine

alcohol to alkyl bromide

PBr3, ether

alkyl halide to grignard

Mg, ether

Grignard to Alkane

D3O+

gilman reagent

R2CuLi

aromatic to aryl bromide

FeBr3/Br2

aromatic to aryl flouride

F-TEDA Bh4

aromatic to aryl nitrate

HNO3, H2SO4

aromatic to aryl chloride

FeCl3/Cl2 OR AlCl3/Cl2

aromatic to aryl iodine

I2/2CuCl2

aromatic to aryl sulfate

SO3/H2SO4

aromatic to SYN cycloalkane (2)

H2P+/EtOH

OR

H2, RH/EtOH

aryl ketone to alkyl arene

H2/Pd

nitroarene to aryl amine (NO2 to NH2 on benzene ring)

2 H2, Pd/C

haloarene to aryl alcohol

OH-, heat, H3O+

haloarene to aryl amine

NH2/NH3

alkyl arene to aryl carboxylic acid

KMnO4, H2O

alkyl aromatic to alpha bromination

NBS, ClC4

2 ways to add benzoic acid to benzene

KMnO4/heat

OR

Na2Cr2O7/H2SO4,H2O

ozonolysis

O3, Zn,H3O+

thiol to sulfide

RX, THF

sulfide to sulfoxide

H2O2, H2O

sulfoxide to sulfone

RCO3H

Ester to aldehyde

DIBAL-H, H3O+

Aldehyde to carboxylic acid

CrO3, H3O+, acetone

ketone to dicarboxylic acid

KMnO4, H2O, NaOH, H3O+

aldehyde/ketone to alcohol (2)

LiAlH4, H3O+

OR

EtMgBr, ether, H3O+

a-B unsaturated aldehyde/ketone to 1,4-addition

nucleophile, H3O+

aldehyde/ketone to imine

R'NH2

aldehyde/ketone to enamine

R2'NH

aldehyde/ketone to alkane (wolf-kishner)

H2NNH2, base, heat

aldehyde/ketone to acetal/ketal

2CH3CH2OH, HCl

aldehyde/ketone to alkene (witting reaction)

R3P=CH2

phenol to quinones (benzene ring with two C=O bonds)

Na₂Cr₂O₇/H2SO4

quinones to hydroquinones

NaBH4, SnCl2

ethylene (CH2=CH2) to ethylene oxide

O2, Ag2O

alcohol to alkene (2)

H3O+, THF, heat

OR

POCl2, pyradine

primary alcohol to aldehyde to carboxylic acid (has to go all the way through to CA, cannot stop) (oxidation)

KMnO4, CrO3, NaCr2O7 (Two of these, one from alcohol --> aldehyde, one from aldehyde --> CA)

secondary alcohol to ketone (oxidation)

KMnO4, CrO3, NaCr2O7 (one of them)

Tertiary alcohols cannot be oxidized because

there are no hydrogen atoms attached to the alcohol carbon

tertiary alcohol to carbonyl (oxidation)

NO REACTION

what alcohol cannot be oxidize to carbonyl

tertiary

primary alcohol to aldehyde

DMP, CH2Cl2

secondary alcohol to ketone

PCC, CH2Cl2

protecting alcohol

(CH3)3SiCl, Et3N

carbonyl to alcohol

NaBH4, ethanol, H+

carboxylic acid/ester to alcohol

LiAlH4, ether, H+

ketone/aldehyde to alcohol

RMgBr, ether, H+

ester to tertiary alcohol

2RMgBr, ether, H+

epoxide to halohydrin

HX, ether

epoxide base opening (to two OH groups)

NaOH, H2O, heat

epoxide base opening (to OH and R)

RMgBr, H3O+

epoxide base opening (to OH, NHR)

RNH2, THF

primary alcohol to ether

H2SO4, heat

Alkyl Halide ---> Ether (Williamson Ether Synthesis)

ROH and RO-X (NEED ALKOXIDE)

alcohol to ether

RI, Ag2O

alkene to ether

Hg(CF3CO2)2, ROH, NaBH4 (mark add of OH)

ether to alcohol and alkyl halide

HX, heat, H2O

allyl aryl ether to ortho alkylation

250 degrees celcius

nitrile to carboxylic acid

NaOH, H2O, H3O+

grignard to carboxylic acid

CO2, THF, H3O+

carboxylic acid to primary alcohol

LiAlH4 (xs), H3O+

primary amide to nitrile

SOcl2, benzene, heat

nitrile to primary amine

LiAlH4 to H2O

nitrile to ketone

1. RMgX 2. H3O+

carboxylic acid to acid chloride

SOCl2

carboxylic acid to acid bromide

PBr3

carboxylic acid to acid anhydride

2 CA + 800 degrees celcius

carboxylic acid to ester (base)

NaH, RX

carboxylic acid to ester (acid)

ROH, HCl

acid chloride to ester

ROH

acid chloride to amide (2)

R2NH

OR

2RNH2

(NO TERTIARY AMINE)

carboxylic acid to amide

DCC, RNH2