Chap9 - 1 Chap 9 Alkynes 1 Nomenclature replace-ane with-yne miners lamps CaC 2 2H 2 O → C 2 H 2 Ca(OH 2 lights methane in the mines 2 Formation

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Unformatted text preview: 1 Chap 9 Alkynes 1. Nomenclature- replace -ane with -yne. miners lamps CaC 2 + 2H 2 O → C 2 H 2 + Ca(OH) 2 lights methane in the mines. 2. Formation of acetylide ions acidic proton Acidity - sp 3 < sp 2 < sp close to nucleus- charge less charge separation Need - NH 2 to pull off H . NaNH 2 = sodium amide a) Can use acetylide ion as a nucleophile. Alkylation b) can act as a base R C C H R C C- + R'-X Sn2 R C C R ' + X- C C H + CH 3 Br N aN H 2 C C C H 3 + Br- R C C- E2 Br + R C C H + + Br- 2 Ex. Synthesize. c) Addition of acetylide ions to carbonyl groups. Ex. H N aN H 2 + CH 3 Br R R R O δ- δ + R R O :- R R R O- H 3 O + R R R OH H C H 3 (1) N aN H 2 (2) H O (3) H 3 O + H 3 C O H C H 3 3 Synthesize: synthesize: 2) synthesis of alkynes by elimination rxns. H C H 3 (1) N aN H 2 (2) (3) H 3 O + HO C H 3 H O H H 2 C (1) N aN H 2 (2) (3) H 3 O + C H 3 O H 3 C C H 3 O H C H 3 4 strong base includes KOH at 200 ° C or NaNH 2 at 150 ° C....
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This note was uploaded on 09/02/2011 for the course CHEM 12a taught by Professor Harrison during the Spring '11 term at West Valley.

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Chap9 - 1 Chap 9 Alkynes 1 Nomenclature replace-ane with-yne miners lamps CaC 2 2H 2 O → C 2 H 2 Ca(OH 2 lights methane in the mines 2 Formation

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