Dolbier HW Solutions 245

Dolbier HW Solutions 245 - a ) with sodium iodide in...

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( d ) Addition of hydrogen chloride to allyl bromide proceeds in accordance with Markovnikov s rule. ( e ) Addition of bromine to allyl bromide gives 1,2,3-tribromopropane. ( f ) Nucleophilic substitution by hydroxide on allyl bromide gives allyl alcohol. ( g ) Alkylation of sodium acetylide using allyl bromide gives the desired 1-penten-4-yne. ( h ) Sodium ammonia reduction of 1-penten-4-yne reduces the triple bond but leaves the double bond intact. Hydrogenation over Lindlar palladium could also be used. 10.23 ( a ) The desired allylic alcohol can be prepared by hydrolysis of an allylic halide. Cyclopentene can be converted to an allylic bromide by free-radical bromination with N -bromosuccinimide (NBS). ( b ) Reaction of the allylic bromide from part (
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Unformatted text preview: a ) with sodium iodide in acetone converts it to the corresponding iodide. 3-Bromocyclopentene 3-Iodocyclopentene Br NaI acetone I NBS heat, peroxides H 2 O Na 2 CO 3 Br OH Cyclopentene 2-Cyclopenten-1-ol 3-Bromocyclopentene Na, NH 3 1,4-Pentadiene H 2 C CHCH 2 CH CH 2 1-Penten-4-yne H 2 C CHCH 2 C CH or H 2 , Lindlar Pd H 2 C CHCH 2 Br CH NaC Allyl bromide 1-Penten-4-yne H 2 C CHCH 2 C CH H 2 C CHCH 2 Br Allyl bromide Allyl alcohol H 2 C NaOH CHCH 2 OH H 2 C CHCH 2 Br Allyl bromide 1,2,3-Tribromopropane BrCH 2 CHCH 2 Br Br 2 Br H 2 C CHCH 2 Br Allyl bromide 1-Bromo-2-chloropropane CH 3 CHCH 2 Br HCl Cl CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS 239...
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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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