Alkynes contain a C C triple bond

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1 Chapter 8: Alkynes: an introduction to organic synthesis Alkynes contain a C C triple bond Acetylene: H-C C-H is the common name for ethyne, used as a torch fuel Alkyne nomenclature follows normal hydrocarbon naming rules: 1. Number from the end closest to the triple bond 2. If it's a tie between the ends to two triple bonds, use branching 3. Double bonds take priority over triple bonds when they are equal distance to the end of a chain. 4. Triple bonds are linear so there is no cis/trans or E/Z, although any double bonds in the molecule can still have stereochemical designators. 8.2 Preparation of alkynes: elimination of dihalides Recall from 7.1 that an alkene can be prepared by elimination of H and Br from an alkyl bromide using KOH. The same can be done (twice) to make an alkyne. This is useful in making an alkyne(triple bond) from an alkene(double bond). As we'll see later, an alkyne can be reduced selectively to either a cisor transalkene, so this can be a way of converting between cis and trans alkenes. ch8 Page 1 ch8 Page 2

2 8.3 Reactions of alkynes: addition of HX Alkynes contain linear (180 o bond angle), sp-hybridized carbons. The triple bond is made of one σand two perpendicular πbonds. Those πbonds can react very similarly to the π bond in an alkene. Addition of HX and X 2 Two equivalents of HBr or HCl can add to an alkyne - both with Markovnikov regiochemistry. H and X usually have trans stereochemistry. Addition of HX to an alkyne takes place via a vinylic carbocation (+ is on a double-bonded C) Halogens can also add twice: ch8 Page 3 ch8 Page 4

3 8.4 Hydration of alkynes and tautomerism Mechanism of mercury(ii)-catalyzed hydration Hydration of alkynes has many ideas in common with hydration of alkenes, but there are some very important differences. Aqueous acid alone will allow Markovnikov hydration of alkenes, but will not react with alkynes. Aqueous acid + catalytic HgSO 4 will readily hydrate alkenes, but the enol produced will rapidly isomerize to a more stable ketone Electrophilic addition of Hg 2+ to make vinylic cation. Nucleophilic addition of H 2 O with loss of proton. Proton from aqueous acid replaces Hg + Proton transfer from O to C in 2 steps converts enol to more stable keto tautomer. (enol intermediate) Tautomerism: rapid isomerization between enoland keto isomers by proton transfer. Hydration is most useful on terminal alkynes(r-c C-H) and symmetrical alkynesbecause it produces only one product. Unsymmetrical internall alkynes make mixtures. ch8 Page 5 ch8 Page 6

4 Hydroboration/oxidation of alkynes BH 3 adds to alkynes in a non-markovnikov orientation to give a vinylic borane. Oxidation makes an enol that tautomerizes to a more stable ketone. Again, unsymmetrical internal alkynes produce a mixture of products. Terminal alkynes produce an aldehydebecause addition is non-markovnikov, opposite of Hg(II)-catalyzed hydration. 8.5 Reduction of alkynes Catalytic hydrogenation with Pd/C gives complete reduction to an alkane just like hydrogenation of alkenes. Reduction with a deactivated catalyst (Lindlar catalyst = "poisoned" Pd on CaCO 3 ) occurs by a syn addition to give a cis alkene. A transalkene can be formed with a dissolving-metal reduction. Addition of H's is stepwise so the more stable trans alkene is formed. ch8 Page 7 ch8 Page 8

5 8.6 Oxidative cleavage of alkynes Alkynes can be cleaved by KMnO 4 or O 3 to make carboxylic acids. This is not so useful synthetically, but can be used to determine the position of triple bonds in alkynes. Ozonolysis of an unknown alkyne gives one 6-carbon dicarboxylic acid HOOC-(CH 2 ) 4 -COOH and 2 equivalents of acetic acid, CH 3 COOH. What is the structure of the unknown alkyne? 8.7 Alkyne acidity: formation of acetylide anions Terminal alkynes are weak acids (pk a ~25). Which direction will the following equilibria lie? HC CH + OH - HC C: - + H 2 O HC CH + NH 2 - HC C: - + NH 3 Molecule pk a CH 4 60 CH 2 =CH 2 44 NH 3 35 HC CH 25 H 2 O 16 NaNH 2 is Na + NH 2- (sodium amide) -a base strong enough to deprotonate terminal alkynes. The conjugate base of an alkyne is called an acetylide ion. (Hydrogens attached to spcarbons are more acidic than sp 2 or sp 3 because the spcarbon anion is more stable) ch8 Page 9 ch8 Page 10

6 8.8 Alkylation of acetylide anions Our first carbon-carbon bond forming reaction is the alkylation of acetylide ions. 8.9 An introduction to multistep organic synthesis Organic synthesisis the process of building complex molecules from simpler ones, one reaction at a time, through a multistep sequence. The acetylide ion is a very strong nucleophile. It can add to electrophilic carbons, displacing one of the other bonds on the carbon. This works best with a 1 o alkyl bromide or iodide. Synthesis of isolated natural products Synthesis of modified natural products Synthesis of new molecules For drug/material design To better understand chemsitry To be successful in mulitstep organic synthesis, you must know the reactions! Starting functional group Functional group produced (regiochemistry, stereochemistry) Reagents used Limitations Careful, this does not work with 2 o or 3 o alkyl halides! ch8 Page 11 ch8 Page 12

7 Retrosynthetic analysis Retrosynthetic analysisis the best strategy for planning syntheses: it's working backwards-first looking at the complex final product you need to make, and considering what reactions could make that product. Synthesis practice Plan a retrosynthesis for the following synthesis problem, then write the full forward sequence of synthetic reactions with reagents. The retrosynthetic analysis uses a two-bar arrow. Carbon-carbon bonds that are "broken" in the retrosynthetic direction are actual carbon-carbon bond forming reactions in the forward direction. Retrosynthetic direction: Forward direction: ch8 Page 13 ch8 Page 14

8 Synthesis practice Plan a retrosynthesis for the following synthesis problem, then write the full forward sequence of synthetic reactions with reagents. Synthesis practice Plan a retrosynthesis for the following compound, starting with compounds with no more than five carbons, then write the full forward sequence of synthetic reactions with reagents. ch8 Page 15 ch8 Page 16

9 Synthesis practice Synthesis practice ch8 Page 17 ch8 Page 18

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