Ch7 - 144 Chapter 6 Reactions o f Alkenes S olutions 145...

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Chapter 7: Alkynes Solutions 145 CHAPTER 7 Solutions te the Problems Problem 7.1 Write the IUPAC name for each compound. (a)~ (b) '. < (e) < Br .1.0ctyne' 3,3·Dimethyl·l·butyne 3-Bromo·3·methyl·l-butyne Problem 7.2 Write the common name ~f each alkyne. (a) (c) ~ .0--== Diisopropylacetylene Cyclohexylacetylene Butylacetylene problem 7.3 Draw a structural fQrmula for an ,alkene and dichlQrQalkime with the given mQlecular formula that yields the indicated alkyne by each reactiQn sequence.' • ' The key to this problem is to realize tlrllt the triple bond in the product is at the same location as the double bond in the.starting material. ' (a) CI 2 * * 2 NaN~ 0i 3 CH:! CH=CHCH 2 CH 3 --=---. .. . CH:! CH:z Cr-:-?HCH 2 3 (cis or trans) C6~2 C 6 H 12 C1i r'H 2 , r'H CI 2 NaNH2 (b) '-'7 14 ... 2 ... . fH3 CHj 2 NaN~ * * I CH:!-CH=CH-f-CH:! CH:!-CH-CH-C-'-CH:! ... I I I' , , , CH c~ 3 (cis traIlS) ~H14CI~ ~H14 Problem 7.4 Draw a structural fQrmula fQr a hydrocarbQn Qf the given mQlecular fQrrimla that undergoes hydrQboration· oxidation to give the indicated prQduct: .' . , Q--y0 (a) 2) H2~, NaOH H 1) BHs ... (b) o-CH= 2 ~H12
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146 Solutions Chapter 7: Alkynes Problem 7 5 Hydration of 2-pentyne gives a mixture of two ketones, each with the molecular formuia CSHlOO. Propose structural formulas for these two ketones and for the enol from which each is derived. The two ketones are 2-pentanone and 3.pentanone. w --- CH:J CH:! CH:!COi 3 2-Pentanone Gf I w CH:J CH:! C=CHCH:J --- CH:JCH:!COi2CH:J 3-Pentanone Problem 7.6 Show ho~~ the synthetic scheme in Example 7.6 might be modified to give the following. (a) l-Heptanol, ' A reduction step can be included using the Lindlar catalyst to give an alkene, that can then be converted to the primary alcohol on the less-substituted carbon of the double bond using hydroboration. , 1. NaNH 2 H 2 HC==CH - HC-C(CH 2 )4CH 3 -----~_~ 2. CH3(CH2hCH2B r Pd/CaC0 3 (Lindlar catalyst) HOCH 2 (CH 2 )sCH 3 I·Heptanol' / (b) 2-Heptanol This ~s the same as part (a), but the last step uses oxymercuration/reduction to place the -01-1 group on the more substItuted carbon of the double bond. Acid catalyzed hydration (HzSOJHzO) could have also been used on the last step. '. , H 2 HC==C(C H2)4CH3 -,-P'-:d-/C-a"""'C-o- --- 3 (Lindlar cata'lyst) OH 1. Hg(OAch, H 2 0 ,. 1* ,2. NaBH 4 CH 3 CH(CH 2 )4CH 3 2:Heptanol Problem 7.7 Enanthotoxin is an extremely poisonous organic compound found in hemlock water dropwart, which is rep~ted to be the most ~isonous plant in Engla~d. It is believed that no British plant has been responsible for more fatal aCCidents, The most pOIsonous part of the plant IS the roots, which resemble small white carrots, oivino the plant the name "five finger death." Also poisonous are its leaves, which look like parsley. Enanthotoxin is thought tointerfere with the Na+ current in nerve cells, which leads to convulsions and death. , OH OH Can show cis-trans isomerism How many stereoisomers are possible for enanthotoxin?
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Ch7 - 144 Chapter 6 Reactions o f Alkenes S olutions 145...

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