Orgo 1 Reactions

HBr

adds halide (Br) mark addition

HBr, ROOR

Adds halide (Br) anti-mark

Br2, CH2CL2

Adds 2 Br's on both sides of double bond (anti)

Br2/ H2O

Adds a Br and OH (Mark addition of OH, Br is the H)

NaI or KI/ acetone

Gets rid of leaving group to form a double bond (alkene)

H2SO4/heat

removes OH, forms double bond (inside only, no terminal alkene)

POCL3/heat

removes OH, forms double bond (terminal)

H3O+

adds OH, mark

Hg(OAc)2, H2O, NaBH4

Mark addition of OH

Hg(OAc)2, CH3OH, NaBH4

Mark addition of O-CH3

BH3/THF, H2O2/OH

anti mark addition of OH

H2/ Pt, Pd, or Ni

turns double bond to single bond, syn addition of H

OsO4/ H2O2

Adds OH to both sides of double bond (syn)

KMnO4/ cold

Adds OH to both sides of double bond (syn)

O3/ CH2CL2, (CH3)2S

Double bond cleavage

O=R-R

O=R-H

O=H-H

KMnO4, warm

Double bond cleavage

O=R-R

O=R-OH

CH2N2, heat

forms cyclopropane from double bond

CH2I2, Zn(Cu)

forms cyclopropane from double bond

MCPBA

forms epoxides from double bond

H30+, H20

opens up epoxides to two OH groups (wedge and dash)

OH, H3O+

opens up epoxides to two OH groups (wedge and dash)

CHCL3, KOH

double bond forms triangle, two chlorines added to tip of it

CHBR3, KOH

double bond forms triangle, two bromines added to tip of it

NaNH2

removes H, forms anion

CH3Br

adds CH3 to anion

NaNH2/ H3O+

Removes Br (or other halide) groups to form a triple bond,

NaNH2 gives terminal alkyne

KOH/200 C

Removes Br (or other halide) groups to form a triple bond,

KOH gives internal alkyne

Br2 (1 eq)

adds two Br groups to triple bond, forms double bond, one cis one trans

HBr (1 eq)

mark syn addition of Br to triple bond, forms double bond

HBr (2 eq)

mark syn addition of 2 Br

HBr, ROOR (alkynes)

anti mark syn addition of Br on triple bond, forms double bond

H2, Pt/Pd/ or Ni

turns triple bond into single bond

H2/Pd (BaSO4), quinoline

triple to double bond with syn addition of H

NaNH3

triple to double bond with anti addition of H

HgSO4/H20

addition of H-OH to triple bonds

formation of Ketone O=C-C

Sia2BH, H202/OH

antimark addition of H-OH to triple bonds

formation of aldehyde O=C-H

KMnO4/ H2O

neutral, cold

oxidizes triple bonds to form carboxylic acid (O=) at triple bond

KMnO4/ H20, OH/heat

cleavage of triple bonds into O=C-OH

if triple bond is terminal, H2O and CO2 form

O3, H2O

cleavage of triple bond, into O=C-OH

Mg, ether

Replaces Br with MgBr

Li, pentane or hexane

replaces halide with Li

O=H-H, H3O+

makes alcohol (OH) from grignard (MgBr)

O=H-R, H3O+

makes alcohol (OH) from grignard (MgBr)

D2O

attaches Detuerium (D) to carbons (replaces MgBr)

NaBH4, EtOH

reduces carboyls (O=) to (-OH)

NaBH4, EtOH with chloride

no reaction

LiAlH4/ ether

reduces carbonyls (O=) to (-OH)

H2, Ra-Ni

reduces carbonyl (O=) to (-OH) and takes away double bonds, to make single bonds

Na2CrO7, H2SO4/H2O

oxidizes alcohol (-OH) to (=O)

CrO3/ H2SO4/H2O, acetone

oxidizes alcohol (-OH) to (=O)

PCC, CH2Cl2

oxidizes alcohol (-OH) to (=O)

Na2CrO7, H2SO4/ H2O

CrO3/ H2SO4/H2O, acetone

turns primary alcohols (-OH) into carboxylic acids (OH=C=O)

TSCI

Forms (OTos) from (OH)

HCl/ ether, 0C

forms alykly halid (-Cl) from alcohols (-OH)

PBr3, CH2CL2

replaces (-OH) with (-Br)

PCl3, CH2CL2

replaces (-OH) with (-Cl)

PI2, CH2CL2

replaces (-OH) with (-I)