Orgo 1 reactions

HX

C=C —> C-X

Adds H,X

Markovnikov

addition of Halide

X2

C=C —> C-X, C-X

Anti

adds X,X

Addition of Halide

X2, H2O

C=C —> C-X, C-OH

adds X and OH

Markovnikov

Anti

Addition of Halide

X2, ROH

C=C —> C-X, ROH

Adds X, ROH

Markovnikov

Anti

Addition of Halide

H2SO4 or H3PO4 and heat

-OH —> C=C

2 and 3rd degree alcohols only

formation of alkene

can rearrange

dehydration reaction

strong base

-X —> C=C

formation of alkene

H20, H2SO4

C=C —> -OH

adds H, OH

hydration reaction

Markovnikov

Hg(OAc)2, H20

NaBH4

C=C —> -OH

adds H, OH

Markovnikov

BH3

NaOH, H2O2

C=C —> OH

adds H, OH

non-markovnikov

syn

hydroboration

KMnO4, Naoh, H20

C=C —> -OH, -OH

adds 2 OH groups

syn

dihydroxylation reaction

OsO4

NaHSO3, H20

C=C —> -OH, -OH

adds 2 OH

syn

dihydroxylation

O3

Zn, H3O+

C=C —> C=O

Oxidative cleavage of alkenes

Cleaves terminal C=C to become aldehydes

Cleaves internal C=C to become ketones

KMnO4, H2O

C=C —> C=O

Oxidative Cleavage of alkenes

terminal alkenes to carboxylic acids

Internal alkenes to ketones

H2, Pd/C

C=C —> H,H

just adds H removes double bond

Syn

Catalytic hydrogenation

CH2N2

C=C —> cyclopropane

adds CH2 carbene

syn

cycloproponation

CHCl3, KOH

C=C —> Cyclopropane

adds CCL carbene

Syn

Cycloproponation

CH2I2, Zn(Cu)

C=C —> cyclopropane

can also use CHRI2 or C(R)2I2

adds the C group to the cyclopropane

syn

Cycloproponation

KOH or NaOH

-X —> -OH

1st degree alcohols only because substitution

2nd and 3rd would go strraight to alkenes because E2 reaction

LAH or NaBH4

C=O —> OH

NaBH4 can only reduce aldehydes and ketones

LAH can reduce all carbonyls including esters

RMgBr or RLi

C=O —> -OH

adds once to aldehydes/ketones

adds twice to esters because it generates a ketone after the first addition that is then reacted with again

doesnt react with carboxylic acids because grignard they act as strong base instead of nucleophile

Mscl or TsCL, pyridine

-OH —> -OMs or -Ots

no inversion occurs

Hx

-OH —> -X

3rd degree alcohols only

Sn1 reaction

PBr3 or SOCL2, pryidine

-OH —> -X

inversion

1st and 2nd degree alcohols only

halogenation of alcohol

POCl3, pryidine

-OH —> C=C

2nd and 3rd degree alcohols only

NO INVERSION

dehydration reaction

KmnO4, H20

Na2Cr2O7, H3O+

CrO3,H2SO4, H2O

PCC

-OH —> C=O

2nd degree form ketones

1st degree form carboxylic acids

PCC turns 1st degree into aldehyde due to lack of water