Ch 6 - Lecture notes 6 PDF

Preview

Summary

chapter 6 reactions...

Description

chem 2211 CH. 6 LINE RXNS ALKENE REACTIONS

SEMESTER PLANS AVAILABLE FOR: General Chemistry, Organic Chemistry, & Calculus 1

ON-CAMPUS PRIVATE TUTORING AVAILABLE FOR: General & Organic Chemistry, STAT 2000, MATH 1101, Pre-Calculus, Calculus 1, BIOL 1107, Biochem 3100, & Physics 1

WWW.NERDDAWGS.ORG | [email protected]

Acid addition in dichloromethane: a hydrogen halide (HCl, HBr, HI) is added to an alkene to form an alkyl halide. Stereochemistry preference: none Regiochemistry: Markovnikov

Acid-catalyzed addition of alcohol: an alcohol is added to an alkene to produce an ether. Stereochemistry preference: none Regiochemistry: Markovnikov

Halohydrin formation: a halogen (bromine/chlorine) is added to an alkene to form a cyclic intermediate and then water is added to form a halohydrin. Stereochemistry preference: Anti

Hydroboration-oxidation adds a hydrogen and water across the double bond to form an anti-Markovnikov alcohol with NO option for carbocation rearrangement. Stereochemistry preference: syn: the H and OH add on the same side. Regiochemistry: anti-Markovnikov

Epoxidation: an epoxide is formed from the reaction of an alkene and a peroxyacid. A peroxyacid is like a carboxylic acid with an extra oxygen, MCPBA is the most common peroxyacid used for this reaction. Stereochemistry preference: syn

Acid-catalyzed addition of water: water is added to an alkene to produce an alcohol. Stereochemistry preference: none Regiochemistry: Markovnikov

Addition of a halogen: a halogen (bromine/chlorine) is added to an alkene to form a 1,2-disubstitutted halo alkane. Stereochemistry preference: Anti: the 2 groups adding acros the double bone are opposite to each other.

Halohydrin formation: an alcohol can be added instead of water. The mechanism is identical to halohydrin formation. Stereochemistry preference: Anti

Oxymercuration-demercuration: forms a Markovnikov alcohol without possibility of rearrangement because the mechanism doesn’t proceed through a carbocation. Stereochemistry preference: none Regiochemistry: Markovnikov

Ozonolysis: cleaves alkenes into 2 carbonyl containing compounds. Reductive Ozonolysis leaves the double bond forming ketones, aldehydes, and formaldehydes.

Ozonolysis: cleaves alkenes into 2 carbonyl containing compounds. Reductive Ozonolysis leaves the double bond forming ketones, aldehydes, and formaldehydes.

Ozonolysis: cleaves alkenes into 2 carbonyl containing compounds. Reductive Ozonolysis leaves the double bond forming ketones, aldehydes, and formaldehydes.

Oxidative Ozonolysis: puts an oxygen where a hydrogen is Oxidative Ozonolysis: puts an oxygen where a hydrogen is t to form ketones, carboxylic acids, and carbon dioxide. (can form ketones, carboxylic acids, and carbon dioxide. (can use use 𝑂3 𝑜𝑟 𝐾𝑀𝑛𝑂4 reagents) 𝑂3 𝑜𝑟 𝐾𝑀𝑛𝑂4 reagents)

Oxidative Ozonolysis: puts an oxygen where a hydrogen is to form ketones, carboxylic acids, and carbon dioxide. (can Addition of hydrogen: 2 H atoms are added across an alken use 𝑂3 𝑜𝑟 𝐾𝑀𝑛𝑂4 reagents) to form an alkane. Stereochemistry preference: syn Regiochemistry: none...