Organic Chemistry - Reactions Exam 4

H2SO4, H+ H2O

Zaitsev

Alcohol -> Alkene

Dehydration

Heat + Metal (elim)

Alkane -> Alkene

Dehydrogenation

Base

Zaitsev

IF bulky base = Hoffmans

Dehydrohalogenation

Bulky Bases

Potassium t-butoxide

triethyl amine

2,6 - dimethyl pyridine

di-isopropyl amine

1) O3 2) (CH3)2S

Ozonolysis

Alkene -> Ketone + Aldehyde

KMnO4 (warm, conc.)

Oxidative cleavage

Alkene -> Ketone + Aldehyde (Carboxylic Acid)

KMnO4, H2O2 (cold, dilute)

Syn Addition

Alkene -> Diol

O2O4, H2O2

Alkene -> diol

Cis-diol

RCO3H

Makovnikov

Weak Peroxyacid: Alkene -> epoxide

Strong Peroxyacid: Alkene -> Open acid ring

Strong Peroxyacids

Peroxyacetic Acid

Peroxyformic Acid

In H3O+

Weak Peroxyacids

Peroxybenzoic Acid

MCPBA

in CCl4

HX, ROOR

Anti-Markovnikov Hydrohalogenation

HX

Markovnikov

Alkene -> Alkyl Halide

X2, H2O

Markovnikov

Anti - addition

Alkene -> halohydrin

X2, CCl4

Vicinal Dihalide, Anti-addition

Alkene -> Dihalide

CH3X, KOH, H2O

Alkene -> Halogenated Cyclopropane

CH2I2,Zn, CuCl

Simmons Smith reagent

alkene part becomes cyclopropene

CH2N2, heat

Alkene -> Cyclopropane

H2, metal

Syn-addition

Alkene -> Alkane

1) Hg(OAc)2 ROH, 2) NaBH4

Markovnikov

Alkene -> Ether

1) Hg(OAc)2 H2O, 2) NaBH4

Markovnikov

Alkene -> Alcohol

1) BH3 THF, 2) H2O2, -OH

Anti-markovnikov

Syn-addition

Alkene -> Alcohol

H2O, H+

Markovnikov

Alkene -> Alcohol

Zaitsev

more substituted alkene

Hoffman

less substituted alkene

Markovnikov

The H atom will always bond to the C with more H

Anti-Markovnikov

electrophile adds to the less substituted carbon

Anti-addition

addition from opposite sides of the double bond

Syn-Addition

addition of constituents to an alkene on the same side of the bond