Dolbier HW Solutions 228

Dolbier HW - 1 NaNH 2 NH 3 2 CH 3 CH 2 CH 2 CH 2 Br HC CCH 2 CH 2 CH 2 CH 3 1-Hexyne HC CH Acetylene 1 HC CCH 2 CH 3 1-Butyne 2HI Hydrogen iodide

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9.33 ( a ) 2,2-Dibromopropane is prepared by addition of hydrogen bromide to propyne. The designated starting material, 1,1-dibromopropane, is converted to propyne by a double dehydrohalogenation. ( b ) As in part ( a ), f rst convert the designated starting material to propyne, and then add hydrogen bromide. ( c ) Instead of trying to introduce two additional chlorines into 1,2-dichloropropane by free- radical substitution (a mixture of products would result), convert the vicinal dichloride to propyne, and then add two moles of Cl 2 . ( d ) The required carbon skeleton can be constructed by alkylating acetylene with ethyl bromide. Addition of 2 mol of hydrogen iodide to 1-butyne gives 2,2-diiodobutane. ( e ) The six-carbon chain is available by alkylation of acetylene with 1-bromobutane.
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Unformatted text preview: 1. NaNH 2 , NH 3 2. CH 3 CH 2 CH 2 CH 2 Br HC CCH 2 CH 2 CH 2 CH 3 1-Hexyne HC CH Acetylene 1 HC CCH 2 CH 3 1-Butyne 2HI Hydrogen iodide 2,2-Diiodobutane CH 3 CCH 2 CH 3 I I NaNH 2 NH 3 CH 3 CH 2 Br HC CCH 2 CH 3 1- Butyne HC C 2 Na 1 Sodium acetylide HC CH Acetylene Propyne CH 3 C CH 1. NaNH 2 , NH 3 2. H 2 O 1,2-Dichloropropane CH 3 CHCH 2 Cl Cl 1,1,2,2-Tetrachloropropane CH 3 CCHCl 2 Cl Cl 2Cl 2 Propyne CH 3 C CH 1,2-Dibromopropane 1. NaNH 2 , NH 3 2. H 2 O CH 3 CHCH 2 Br Br 2,2-Dibromopropane CH 3 CCH 3 Br Br 2HBr Propyne CH 3 C CH 1,1-Dibromopropane CH 3 CH 2 CHBr 2 1. NaNH 2 , NH 3 2. H 2 O 1 2HBr Hydrogen bromide Propyne CH 3 C CH 2,2-Dibromopropane CH 3 CCH 3 Br Br 222 ALKYNES...
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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