Basic Organic Chemistry

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1 Basic Organic hemistry ourse code: EM (Pre-requisites : EM 11122) hapter 04 hemistry of Alkynes Dr. Dinesh R. Pandithavidana Office: B1 222/3 Phone: (+94) (Mobile) dinesh@kln.ac.lk

2 Introduction Alkynes contain a triple bond. General formula is n 2n-2 Two elements of unsaturation for each triple bond. Some reactions are like alkenes: addition and oxidation. Some reactions are specific to alkynes. 2

3 Nomenclature: IUPA Find the longest chain containing the triple bond. hange -ane ending to -yne. Number the chain, starting at the end closest to the triple bond. Give branches or other substituents a number to locate their position. 3

4 Name these: 3 propyne Br bromo-2-pentyne ,6-dimethyl-3-heptyne 4

5 Physical Properties Nonpolar, insoluble in water. Soluble in most organic solvents. Boiling points similar to alkane of same size. Less dense than water. 5 Up to 4 carbons, gas at room temperature.

6 Electronic Structure The sigma bond is sp-sp overlap. The two pi bonds are unhybridized p overlaps at 90, which blend into a cylindrical shape. 6 =>

7 Bond Lengths More s character, so shorter length than alkenes or alkanes. Three bonding overlaps, so shorter. Bond angle is 180, so linear geometry. 7

8 Acidity Table 8

9 Acidity of Alkynes Terminal alkynes, R- -, are more acidic than other hydrocarbons. Acetylene acetylide by N 2-, but not by O - or RO -. More s character, so pair of electrons in anion (sp orbital) is held more closely to the nucleus. Less charge separation, so more stable. 9

10 Synthesis of Alkynes 1. Dehydrohalogenation of Vicinal Dihalides + KO = + KX + 2 O X X X = + NaN 2 + NaX + N 3 X 10

11 + 2 KO + KX + 2 O heat X X KO; then NaN Br Br + 2 KO, heat 11

12 X 2 1. KO alkene vicinal dihalide alkyne 2. NaN 2 Br 2 1. KO 3 = Br Br 3 2. NaN 2 12

13 Forming Acetylide Ions NaN 2 is produced by the reaction of ammonia with sodium metal. + can be removed from a terminal alkyne by sodium amide, NaN 2 13

14 2. Alkynes from Acetylides Acetylide ions are good nucleophiles. S N 2 reaction with 1 alkyl halides lengthens the alkyne chain. 14

15 R- - Na + + R X R- -R + NaX a) S N 2 b) R X must be 1 o or 3 X 3 - Li Br note: R-X must be 1 o or 3 to get S N 2! 3 Na Br 3 o alkyl halide E2 elimination! 15

16 Addition Reactions Similar to addition to alkenes Pi bonds become two sigma bonds. Usually exothermic One or two molecules may add. 16

17 Addition of ydrogen Add lots of 2 with metal catalyst (Pd, Pt, or Ni) to reduce alkyne to alkane, completely saturated. Use a special catalyst, Lindlar s catalyst to convert an alkyne to a cis-alkene. React the alkyne with sodium in liquid ammonia to form a trans-alkene. 17

18 Lindlar s atalyst Powdered BaSO 4 coated with Pd, poisoned with quinoline. 2 adds syn, so cis-alkene is formed. 18 =>

19 Na in Liquid Ammonia Use dry ice to keep ammonia liquid. As sodium metal dissolves in the ammonia, it loses an electron. N 3 + Na N + Na + 3 e - The electron is solvated by the ammonia, creating a deep blue solution. 19

20 Mechanism 20

21 Addition of alogens l 2 and Br 2 add to alkynes to form vinyl dihalides. May add syn or anti, so product is mixture of cis and trans isomers. Difficult to stop the reaction at dihalide. 3 3 Br 2 3 Br Br Br 3 Br Br 2 Br Br 3 Br 21 Br 3

22 Addition of X l, Br, and I add to alkynes to form vinyl halides. For terminal alkynes, Markovnikov product is formed, otherwise a mixture for internal alkynes. If two moles of X is added, product is a geminal dihalide. Br Br Br Br 3 3 Br 22

23 Br with Peroxides Anti-Markovnikov product is formed with a terminal alkyne. Br 3 3 ROOR Br Br 3 Br ROOR Br 23

24 ydration of Alkynes Mercuric sulfate in aqueous sulfuric acid adds -O to one pi bond with a Markovnikov orientation, forming a vinyl alcohol (enol) that rearranges to a ketone. ydroboration-oxidation adds -O with an anti-markovnikov orientation, and rearranges to an aldehyde. 24

25 Mechanism for Mercuration Mercuric ion (g 2+ ) is electrophile. Vinyl carbocation forms on most-substituted carbon Water is the nucleophile. g + g O g + 3 O O O O an enol O + g + 25

26 Enol to Keto (in Acid) Add + to the = double bond. Remove + from O of the enol. 26

27 27

28 ydroboration Reagent Di(secondary isoamyl)borane, called disiamylborane. Bulky, branched reagent adds to the least hindered carbon. Only one mole can add B

29 ydroboration - Oxidation B and add across the triple bond. Oxidation with basic 2 O 2 gives the enol. 3 Sia 2 B 2 O 2 3 NaO 3 BSia 2 an enol O 29

30 Enol to Keto (in Base) + is removed from O of the enol. Then water gives + to the adjacent carbon. 3 O O 3 O 3 O An aldehyde 3 O O 30

31 Oxidation Alkynes KMnO 4 R- -R hot KMnO 4 ROO + OOR carboxylic acids O 3 ; then Zn, 2 O 31

32 KMnO OO + OO hot KMnO 4 3OO + O O 3 ; then Zn, 2 O 2 3 OO 32

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