9.4: Structure and Bonding in Alkynes: sp Hybridization

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1 hapter 9: Alkynes 9.1: Sources of Alkynes (please read) 9.2: Nomenclature Systematic Nomenclature: Prefix-Parent-Suffix Naming Alkynes: Suffix: -yne Many of the same rules for alkenes apply to alkynes 1. Number the carbon chain from the end of the carbon nearest the triple bond 2. The alkyne position is indicated by the number of the alkyne carbon in the chain 3. ompounds with two triple bonds are referred to as diynes, three triple bonds as triynes, etc 9.3: Physical Properties of Alkynes (please read) : Structure and Bonding in Alkynes: sp ybridization acetylene (ethyne) bond angles: -- = 180 (linear geometry bond distances: - = 106 pm = 120 pm Each carbon is sp hybridized linear geometry bond consists of one σ bond (sp hybridized orbitals) and two π bond (unhybridized p-orbitals) (see ch. 2 notes) Bond dissociation energies (Δ - ) Δ = = 611 KJ/mol Δ = 820 KJ/mol Δ = 368 KJ/mol Δ = 368 KJ/mol π -bond = 243 KJ/mol π-bonds = 452 KJ/mol 226 KJ/mol per π -bond The π-bond of an alkene is ~17 KJ/mol more stable than the π-bond of an alkyne

2 hybridization of sp 3 sp 2 sp geometry tetrahedral trigonal planar linear Δ - Δ - % s character pk a 111 pm ~ pm 368 kj/mol 410 kj/mol 25% pm ~ pm 611 kj/mol 452 kj/mol 33% pm 120 pm 820 kj/mol 536 kj/mol 50% : Acidity of Acetylene and Terminal Alkynes In general, the - bond of hydrocarbons are very weak acids. The - - bond of a terminal acetylene is weakly acid, pk a ~26. _ pk a = 60 _ pk a = 45 _ pk a = 26 A strong base can deprotonate terminal acetylenes to generate an acetylide anion. _ B: Na _ B: Na pk a = 26 pk a = 208 2

3 9.6: Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes - Acetylide anions are strong nucleophiles and will undergo nucleophilic substitution reactions with primary alkyl halides, resulting in the formation of a - bond. _ Br Na Alkylation of acetylide anions is a general method of making higher alkynes from simpler alkynes. TF S N 2 2 N: Na new - bond formed NaBr Br pentyne pentyne 2 N: Na I hexyne 209 Alkylation of acetylide anions is generally limited to primary alkyl halides. Acetylide anions act as a base with secondary and tertiary alkyl halides resulting in E2 elimination. 9.7: Preparation of Alkynes by Elimination eactions Double dehydrohalogenation reaction 2 vicinal dihalide NaN 2 NaN 2 NaN 2 geminal dihalide 3 equivalents of NaN 2 are required for preparing terminal alkynes from from 1,2- or 1,1-dihaloalkane

4 9.8: eactions of Alkynes - alkynes undergo addition reactions similar to alkenes. Increasing oxidation state l l l l l 9.9: ydrogenation of Alkynes - The hydrogenation of an alkyne cannot be stopped at the alkene stage under normal hydrogenation conditions ( 2, metal catalyst) l 1 2 2, Pd/ 1 2 2, Pd/ 1 2 cis alkene intermediate 211 The π-bonds of alkenes are slightly more reactive toward hydrogenation than the π-bond of an alkene. Lindlar s catalyst: poisoned palladium catalyst Pd on a 3 Pb(Ac) 4 quinoline (amine) poisons reduce the catalysts activity so only the most reactive functional groups are hydrogenated 1 2 2, Lindlar's atalyst 1 2 cis -addition of 2 ydrognation can be stopped at the cis-alkene stage with Lindlar s catalyst 9.10: Metal-Ammonia eduction of Alkynes - Dissolving Metal eduction: Li(0) metal in liquid ammonia (N 3 ) Li(0) in N 3 e (solvated electron) Li, N 3, ( 3 ) trans-alkene 212 4

5 9.11: Addition of ydrogen alides to Alkynes Addition of to acetylenes: Markovnikov addition only useful for terminal or symmetrical acetylenes ( 1 = 2 ) vinyl halide 2 trans addition of Mechanism? rate = k [alkyne][] 2 vinyl carbocation 213 arbocation Stability > > ~ > ~ 3 alkyl 2 alkyl 1 alkyl 2 vinyl methyl carbocation 1 vinyl gem-dihaloalkanes are obtained with excess - addition follows Markovnikov s rule 2 = or 2 = excess gem-dihaloalkane Anti-Markovnikov addition of Br to terminal alkynes in the Presence of peroxides (radical mechanism) Br peroxides 1 Br 1 Br 214 5

6 9.13: Addition of alogens to Alkynes : ydration of Alkynes Alkenes hydration 2 anti addition of 2 Alcohols excess Alkynes hydration Ketones or Aldehydes g (II) catalyzed hydration of alkynes: similar to oxymercuration - Markovnikov Addition gs 4, 2 S 4, 2 1 enol tautomerization 3 methyl ketone 215 Tautomerization - equilibrium between two isomers (tautomer), which differ by the migration of a proton and a π-bond. Keto-enol tautomerization - normally favors the keto form (=) = Δ = 611 KJ/mol enol keto = Δ = 735 KJ/mol Keto-enol tautomerization is acid-catalyzed 216 6

7 ydroboration of Alkynes - anti-markovnikov hydration of an alkyne (complementary to the g(ii) catalyzed method) 1) B 3, TF 2) 2 2, Na Aldehyde product g(ii)-catalyzed hydration and hydroboration are equivalent for internal alkynes 1) B 3, TF 2) 2 2, Na gs 4, 2 S 4, Ketone products ydration of an internal alkyne is only useful for symmetrical acetylenes ( 1 = 2 ) : zonolysis of Alkynes zonolysis of alkenes (sect. ): ) 3 2) Zn ketones and aldehydes zonolysis of Alkynes terminal alkyne 1) 3 2) Zn arboxylic acid 2 3 1) 3 2) Zn internal alkyne arboxylic acids Alkynes are less reactive toward ozonolysis than alkenes. An alkenes can be oxidatively cleaved by ozone in the presence of an alkyne

8 - bond forming reactions are important for organic synthesis Prepare octane from 1-pentyne Prepare (Z)-2-hexene from 1-pentyne Z-2-hexene Prepare 4-octanone from acetylene 219 8

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