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Dolbier HW Solutions 224 - 218 ALKYNES(c CH3CH2C CCH2CH3...

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( c ) ( d ) ( e ) ( f ) ( g ) ( h ) ( i ) 9.28 The two carbons of the triple bond are similarly but not identically substituted in 2-heptyne, CH 3 C > CCH 2 CH 2 CH 2 CH 3 . Two regioisomeric enols are formed, each of which gives a different ketone. O CH 3 CCH 2 CH 2 CH 2 CH 2 CH 3 CH 3 C CCH 2 CH 2 CH 2 CH 3 2-Heptyne CH 3 C OH CHCH 2 CH 2 CH 2 CH 3 2-Hepten-2-ol 2-Heptanone O CH 3 CH 2 CCH 2 CH 2 CH 2 CH 3 CH 3 CH OH CCH 2 CH 2 CH 2 CH 3 2-Hepten-3-ol 3-Heptanone H 2 O, H 2 SO 4 HgSO 4 3-Hexyne 1. O 3 2. H 2 O Propanoic acid 2CH 3 CH 2 COH O CH 3 CH 2 C CCH 2 CH 3 3-Hexyne H 2 O, H 2 SO 4 HgSO 4 3-Hexanone CH 3 CH 2 CCH 2 CH 2 CH 3 O CH 3 CH 2 C CCH 2 CH 3 3-Hexyne Cl 2 (2 mol) CH 3 CH 2 C CCH 2 CH 3 3,3,4,4-Tetrachlorohexane CH 3 CH 2 C Cl CCH 2 CH 3 Cl Cl Cl
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