Dolbier HW Solutions 221

Dolbier HW Solutions 221 - 3 3 DMSO CH HC Acetylene CH CH 3...

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( g ) ( h ) 9.20 Ethynylcyclohexane has the molecular formula C 8 H 12 . All the other compounds are C 8 H 14 . 9.21 Only alkynes with the carbon skeletons shown can give 3-ethylhexane on catalytic hydrogenation. 9.22 The carbon skeleton of the unknown acetylenic amino acid must be the same as that of homoleucine. The structure of homoleucine is such that there is only one possible location for a carbon carbon triple bond in an acetylenic precursor. 9.23 ( a ) ( b ) ( c ) ( d ) 1-Hexene is then converted to 1-hexyne as in part ( b ). 9.24 ( a ) Working backward from the f nal product, it can be seen that preparation of 1-butyne will allow the desired carbon skeleton to be constructed. CH 3 CH 2 C CCH 2 CH 3 3-Hexyne CH 2 CH 2 C C 2 BrCH 2 CH 3 1 prepared from CH 2 CH 3 CH 2 CH 2 CH 2 CH 1-Hexene CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 I 1-Iodohexane KOC(CH
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Unformatted text preview: 3 ) 3 DMSO CH HC Acetylene CH CH 3 CH 2 CH 2 CH 2 C 1-Hexyne C 2 Na 1 HC NaNH 2 NH 3 CH 3 CH 2 CH 2 CH 2 Br 1-Hexene 1,2-Dibromohexane CH CH 3 CH 2 CH 2 CH 2 C CH 3 CH 2 CH 2 CH 2 CH CH 2 1-Hexyne Br 2 CCl 4 1. NaNH 2 , NH 3 2. H 2 O CH 3 CH 2 CH 2 CH 2 CHCH 2 Br Br 1. NaNH 2 , NH 3 2. H 2 O CH 3 CH 2 CH 2 CH 2 CH 2 CHCl 2 1,1-Dichlorohexane CH CH 3 CH 2 CH 2 CH 2 C 1-Hexyne HC CCHCH 2 CHCO 2 CH 3 1 NH 3 O CH 3 CH 2 CHCH 2 CHCO 2 CH 3 1 NH 3 O H 2 Pt C 7 H 11 NO 2 Homoleucine H 2 Pt or or 3-Ethyl-1-hexyne 4-Ethyl-1-hexyne 4-Ethyl-2-hexyne 3-Ethylhexane 3-Ethyl-3-methyl-1-pentyne is CH 3 CH 2 CC CH 2 CH 3 CH 3 CH C Ethynylcyclohexane is CH ALKYNES 215...
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