Dolbier HW Solutions 386

Dolbier HW Solutions 386 - C 6 H 5 CH 2 SH NaOH, H 2 O

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
( c ) Dehydration of the aldol addition product occurs when the reaction is carried out at elevated temperature. ( d ) Lithium aluminum hydride reduces the aldehyde function to the corresponding primary alcohol. ( e ) A characteristic reaction of a , b -unsaturated carbonyl compounds is their tendency to undergo conjugate addition on treatment with weakly basic nucleophiles. 18.23 ( a ) Ketones undergo a halogenation by way of their enol form. ( b ) The combination of C 6 H 5 CH 2 SH and NaOH yields C 6 H 5 CH 2 S 2 (as its sodium salt), which is a weakly basic nucleophile and adds to a , b -unsaturated ketones by conjugate addition. ( c ) Bromination occurs at the carbon atom that is a to the carbonyl group. Br 2 diethyl ether C 6 H 5 O C 6 H 5 2,2-Diphenylcyclo- pentanone C 6 H 5 O Br C 6 H 5 2-Bromo-5,5- diphenylcyclopentanone (76%) H 3 C C(CH 3 ) 2 O 2-Isopropylidene-5- methylcyclohexanone
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: C 6 H 5 CH 2 SH NaOH, H 2 O 2-(1-Benzylthio-1-methylethyl)-5-methylcyclohexanone (89 90%) H 3 C C(CH 3 ) 2 SCH 2 C 6 H 5 H O CCH 2 CH 3 Cl O 1-( o-Chlorophenyl)-1-propanone CCHCH 3 Cl Cl O 2-Chloro-1-( o-chlorophenyl)-1-propanone Cl 2 CH 2 Cl 2 HC O C 6 H 5 CH 2 CH 2 CH CCH 2 C 6 H 5 2-Benzyl-5-phenyl-2-pentenal HC CN O C 6 H 5 CH 2 CH 2 CHCHCH 2 C 6 H 5 2-Benzyl-3-cyano-5-phenylpentanal NaCN H 1 CH 2 OH C 6 H 5 CH 2 CH 2 CH CCH 2 C 6 H 5 2-Benzyl-5-phenyl-2-penten-1-ol HC O C 6 H 5 CH 2 CH 2 CH CCH 2 C 6 H 5 2-Benzyl-5-phenyl-2-pentenal 1. LiAlH 4 2. H 2 O HC O C 6 H 5 CH 2 CH 2 CH CCH 2 C 6 H 5 2-Benzyl-5-phenyl-2-pentenal O 2C 6 H 5 CH 2 CH 2 CH 3-Phenylpropanal NaOH ethanol, 70 8 C 480 ENOLS AND ENOLATES...
View Full Document

Ask a homework question - tutors are online