Substitution and Elimination Reactions

Substitution and Elimination Reactions - Tertiary and...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
S N 2 Reactions Reactivity Order: Me > 1° > 2° Only the inverted product is formed The bulkier the reaction, the slower the reaction Rate depends on the concentration of both the alkyl halide and the nucleophile E2 Reactions Reactivity Order: 3° > 2° > 1° > Me Both E and Z stereoisomers are formed (more of the stereoisomer with the bulkiest groups on opposite sides of the double bond) S N 1 Reactions Reactivity Order: 3° > 2° Both stereoisomers ( R and S ) are formed The more methyl groups, the faster the reaction Rate depends only on the concentration of the alkyl halide E1 Reactions Reactivity Order: 3° > 2° Both E and Z stereoisomers are formed (more of the stereoisomer with the bulkiest groups on opposite sides of the double bond) Reactions with Alcohols Addition of HX to an alcohol produces an alkyl halide Addition of H 2 SO 4 and heat dehydrates alcohols and results in an alkene plus water
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Tertiary and secondary alcohols undergo E2 dehydration Primary alcohols undergo E1 dehydration Oxidation works only on primary and secondary alcohols using chromic acid Primary alcohols are oxidized to aldehydes and carboxylic acids (stops at aldehyde if PCC is used) Secondary alcohols are oxidized to ketones Cleavage of Ethers ROR + HX ROH + RX Ring-Opening Reactions of Epoxides Nucleophiles in acid-catalyzed reactions attack the most substituted carbon Nucleophiles in basic-catalyzed reactions attack the least substituted carbon Most Reactive Least Reactive RI > RBr > RCl > RF The weaker the base, the better the leaving group. The stronger the base, the better the nucleophile. Bromination is more selective than chlorination Both bromination and chlorination require heat or light to occur...
View Full Document

Page1 / 2

Substitution and Elimination Reactions - Tertiary and...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online