Organic Chemistry: Alcohols, Ethers, Alkenes, Alkynes Mechanisms

Making Ethers mechanism

alcohol - ether (SN2)

Making Alcohols (primary) mechanism

alkyl halide - alcohol (SN2)

Elimination of primary alcohols mechanism

alcohol - alkene (E2)

Elimination of primary alcohol reagents

POCL3 + pyridine/strong acids (H3SO4, H3PO4, TsOH))

Substitution of primary & secondary alcohols

alcohol - alkyl halide (SN2)

Substitution of primary & secondary alcohol reagents

HX/PBr3/SOCl2/TsCl + pyridine

Oxidation of primary alcohol mechanisms

alcohol - aldehyde (PCC) or carboxylic acid

Oxidation of primary alcohol reagents

PCC (aldehyde), CrO3, Na2CrO7, K2Cr2O7 (carboxylic acid)

Oxidation of secondary alcohol mechanism

alcohol - ketone

Oxidation of secondary alcohol reagent

PCC (under acidic conditions)

Elimination of secondary and tertiary alcohols mechanism

alcohol - alkene (E1)

Elimination of secondary and tertiary alcohol reagents

POCl3 + pyrimidine/strong acid

epoxidation mechanism

alkene - epoxide

epoxidation reagents

peroxyacid/mCPBA

Dihydroxylation (anti-addition) mechanism

alkene - trans-diol

Dihydroxylation (anti-addition) reagents

mCPBA

Dihydroxylation (syn-addition) mechanism

alkene - cis-diol

Dihydroxylation (syn-addition) reagents

KMnO4/OsO4

hydrohalogenation (alkene) mechanism

alkene - akyl halide

hydrohalogenation (alkene) reagents

HX

hydration (alkenes) mechanism

alkene - alcohol

hydration (alkenes) reagents

H3O+

halogenation (alkene) mechanism

alkene - dihalide

halogenation (alkene) reagent

X2

oxidative cleavage of alkenes (ozonolysis) mechanism

alkene - ketone and aldehyde

oxidative cleavage of alkenes (ozonolysis) reagents

O3

halohydrin (alkene) mechanism

alkene - halohydrin (X & OH groups)

halohydrin (alkene) reagents

X2 & H2O

hydroboration - oxidation (alkene) mechanism

alkene - alcohol

hydroboration - oxidation (alkene) reagent

BH3/H2O2, HO

Halogenation (alkyne) mechanism

alkyne - tetrahalide

Halogenation (alkyne) reagents

2 X2

hydrohalogenation (alkyne) mechanism

alkeye - geminal dihalide

hydrohalogenation (alkyne) reagents

2 HX

Reduction of alkyne mechanism

alkyne - alkane (H2/Pdc)/ alkyne - cis alkene (H2/Lindlar)/ alkyne - trans alkene (Na/NH3)

Reduction of alkyne reagents

H2/Pdc, H2/Lindlar, Na/NH3

Oxidative cleavage of alkynes mechanism

alkyne - carboxylic acid +/ CO2

Oxidative cleavage of alkynes reagents

O3

hydroboration/oxidation of alkynes mechanism

alkyne - ketone (internal alkyne) or aldehyde (terminal alkyne )

hydroboration/oxidation of alkynes reagents

BH3/RBH2//H2O2,OH

hydration (alkyne) mechanism

alkyne - ketone

hydration (alkyne) reagents

H2O/H2SO4 or HgSO4)