212 LSW ALKYNES S04. Alkynes
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1 Alkynes Doubly unsaturated functional group Terminal alkynes, R-- 1) 2) 3) 4) Nomenclature: Functional group suffix = Disubstituted alkynes, R--R' Monosubstituted alkynes, R-- Stability: Substituted alkynes The "extra" bond in an alkyne bond by kj/mol or kcal/mol 171 than the alkene h 1-hexyne = kj/mol or kcal/mol h 1-hexene = kj/mol or kcal/mol - = = kj/mol or kcal/mol = - - = kj/mol or kcal/mol
2 Rank 1-hexyne (terminal) and 3-hexyne(internal) for each of the following properties: eat of eat of hydrogenation formation eat of Stability combustion Structure: ybridization: Shape: Y Y Physical Properties: Polarity: Volatililty: Melting points: Boiling points: Aqueous solubility: rganic solubility: Acidity: pka = 172
3 Reactivity: Alkynes act as nucleophiles. Addition reactions: Terminal alkynes: R-- R B: R Acetylide ion: + -B 173
4 Reactions: Alkyne Preparation ydrogenation Metal Reduction ydrogen alides NaN 2 NaN 2 2 / atalyst Na / N 3 (l) + 1 xs ydration g 2+ alogenation 2 zonolysis + 3 Then 2 + Deprotonation B: R R Alkylation 1. NaN 2 R R 2. R' + -B R' 174
5 Preparation of Alkynes Reaction Type: verall reaction: Leaving groups: Requires: NaN NaN Regioselectivity: Stereospecificity: Mechanism: Leaving Group Base: Selectivity: B: LG + LG 175
6 What is the alkyne product from the reactions of the following with NaN 2 : 1,2-dibromopropane 2,3-dibromooctane 1,2-dibromohexane 2,2-dibromohexane Synthesis: Try it: 2-methyl-4-octene 2-methyl-4-octyne E2 mechanism (For both alkenes and alkynes) Leaving Groups: -LG Base: B 176
7 Stereochemistry E2 reactions 180º 0º Synperiplanar Regioselectivity: Zaitsev's rule: Zaitsev product: offman product: Stereoselectivity: 177
8 Addition Reactions of Alkynes Two factors influence the relative reactivity of alkynes compared to alkenes: ydrogenation of Alkynes 2 / atalyst Reaction type: verall reaction: Regioselectivity: Stereoselectivity: Requirements: Alkanes: Alkenes: Lindlar's catalyst: Pd / a 3 / quinoline Mechanism: ATALYTI YDRGENATIN Step 1: Step 2: Step 3: Step 4: 178
9 Dissolving Metal Reduction of Alkynes Na / N 3 (l) Reaction type: verall reaction: Reactivity order: Regioselectivity: Stereoselectivity: Requirements: Mechanism: Step 1: Step 2: Step 3: Step 4: 3 3 Na 3 + Na 3 N N Na NaN Na 2 Synthesis: ow would you prepare trans 2-pentene from cis 2-pentene? 3 179
10 Reaction of Alkynes with ydrogen alides + 1 Reaction type: verall reaction: Reactivity order: Regioselectivity: 3 Stereoselectivity: Requirements: xs h 3 3 Mechanism: + Br - Br Br Br
11 ydration of Alkynes + 2 Reaction type: verall reaction: Regioselectivity: Stereoselectivity: Requirements: Mechanism: g Tautomerization: enol and keto: N T N N N N A N N N T N N N N G N 181
12 alogenation of Alkynes Reaction type: verall reaction: Reactivity order: Regioselectivity: Stereoselectivity: 2 Requirements: Mechanism: Br Br Br + _ + Br Br Br 182
13 zonolysis of Alkynes Then 2 Reaction type: verall reaction: Requirements: Mechanism: What would be the products of the ozonolysis: ethyne? 1-butyne? 2-butyne? cyclooctyne? 183
14 Acidity of Terminal Alkynes B: R R + -B Terminal alkynes: Stability of the conjugate base (i.e. the carbanion). s character: (sp = %, sp 2 = % and sp 3 = %) Increased s = = onjugate base of alkyne = = Mechanism: B: R R ould you use a Na or NaEt for this reaction? pka 2 = pka 3 2 = pka N 3 = + -B 184
15 Alkylation of Alkynes: Acetylide ion: 1. NaN 2 R R 2. R' Reaction type: verall reaction: Reactivity order: Alkyne: Alkyl halide: alide: Regioselectivity: Stereoselectivity: Requirements: R' Mechanism: _ R 2 Br 3 N N R 185
16 Examples: Ethylene (acetylene): monosubstituted (R--): symmetrical (R = R'): R--R': unsymmetrical (R R') R--R': Problems to try: 1. What is the product of the reactions of with: (a) 2-bromopropane (b) ethanol (c) 1-iodooctane (d) ethyl tosylate (e) (R)-2-bromohexane (f) bromobenzene 2. What would be the product from the reaction of propene with the following reagent sequence: (i) Br 2 (ii) NaN 2, heat (iii) NaN 2 then MeI Final product: 186
17 3. For the reaction 2-butyne with Br: (i) reaction with 1 equivalent gives 2-bromo-2-butene (ii) reaction with excess gives 2,2-dibromobutane (a) What conclusions can you reach about the reactivity of 2-bromo-2-butene compared to 2-butyne? (b) onsider the two possible carbocations that could be formed in the conversion of 2-bromo-2-butene to 2,2-dibromobutane. Suggest a reason for the observed regioselectivity. 5. Show the major products, with stereochemistry where applicable, for the reactions of: With: 1-pentyne 2-pentyne (i) excess 2 / Pd (ii) 2 / Lindlar Pd (iii) Na / N 3 (iv) 1 equiv. l (v) excess l (vi) aq. 2 S 4, gs 4 (vii) excess Br 2 (viii) 3 then 2 187
sp 2 geometry tetrahedral trigonal planar linear ΔH C-C ΔH C-H % s character pk a 464 KJ/mol 33% 44
hapter 10: Alkynes 10.1 Introduction to Alkynes ~ 111 ~ 122 1.06 Å 180 1.1 Å ~ 116 1.08 Å 1.54 Å 1.34 Å 1.20 Å hybridization of sp 3 sp 2 sp geometry tetrahedral trigonal planar linear 368 KJ/mol 632 KJ/mol
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