218 ALKYNES () CH,CHC= CCH,CH31-A,→ CH,CH3 (E)3-Hexene CH CH2 (d)CHCH2C≡CCH2CH3 (I mol) CHCH (Z)-3-Chloro-3-hexene (e)CHCH2C≡CCH2CH2 (2 mol) CH3CH,,,CH 3-Hexyne 3.3-Dichlorohexane (f)CH3CH2C≡CCH2CH (I mol (E)-3, 4-Dichloro-3-hexer (g)CHCH2C≡CCH2CH CHCH,C—CCH2CH H.O. H (h) CH3=CCH2 CH3 Hgse CH,CHCCH,CH,CH 3-Hexyne (i)CH2CH2C≡CCH2CH2 2CH,. COH 9.28 The two carbons of the triple bond are similarly but not identically substituted in 2-heptyne CHaCECCH,,,CH3. Two regioisomeric enols are formed, each of which gives a different CHC≡CCH2CH2CH2CH CHa C=CHCH, CH, CH, CH3 CH,CH=CCH, CH,CH, CH3 2-Heptyne 2-Hepten-2-oI 2-Hepten-3-ol CHa CCH,CH,,: CH CHCCHCHCHCH Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website(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, CH3C>CCH2CH2CH2CH3. Two regioisomeric enols are formed, each of which gives a different ketone. O CH3CCH2CH2CH2CH2CH3 CH3C CCH2CH2CH2CH3 2-Heptyne CH3C OH CHCH2CH2CH2CH3 2-Hepten-2-ol 2-Heptanone O CH3CH2CCH2CH2CH2CH3 CH3CH OH CCH2CH2CH2CH3 2-Hepten-3-ol 3-Heptanone H2O, H2SO4 HgSO4 3-Hexyne 1. O3 2. H2O Propanoic acid 2CH3CH2COH O CH3CH2C CCH2CH3 3-Hexyne H2O, H2SO4 HgSO4 3-Hexanone CH3CH2CCH2CH2CH3 O CH3CH2C CCH2CH3 3-Hexyne Cl2 (2 mol) CH3CH2C CCH2CH3 3,3,4,4-Tetrachlorohexane CH3CH2C Cl CCH2CH3 Cl Cl Cl 3-Hexyne Cl2 (1 mol) CH3CH2C CCH2CH3 C C Cl CH3CH2 CH2CH3 Cl (E)-3,4-Dichloro-3-hexene 3-Hexyne HCl (2 mol) CH3CH2C CCH2CH3 3,3-Dichlorohexane CH3CH2CCH2CH2CH3 Cl Cl 3-Hexyne HCl (1 mol) CH3CH2C CCH2CH3 C C Cl CH3CH2 CH2CH3 H (Z)-3-Chloro-3-hexene 3-Hexyne Li NH3 CH3CH2C CCH2CH3 C C H CH3CH2 CH2CH3 H (E)-3-Hexene 218 ALKYNES Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website