2004FINAL_ANSWER

2004FINAL_ANSWER - product MANY answers were accepted, as...

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Answers Final Exam 2004 Multiple Choices are 3 points each (corrected automatically) # V1 1 c 2 d 3 d 4 b 5 a 6 c 7 d 8 b 9 a 10 a 11 b 12 b 13 a 14 d 15 a 16 b 17 c 18 a 19 a 20 b 21 b 22 5>3>2>1>4 Short answers (not in order): OHC O N N OCH 3 N N N O N O
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HN O NH 2 O O CO 2 H CO 2 H H 2 N O Ph OCH 3 Multistep synthesis (6 points). MANY answers were accepted, as long as it had a chance of working based on what we have learned One possible answer for 25 : -aldol reaction with OHC-CH2-CO-CH3 and NaOH (CH2 will be deprotonated and will attack the aldehyde of starting material to form an alcohol -ether formation on that alcohol using NaH and CH3Br -use Mg to form the Grignard which will attack the aldehyde intramolecularly and give and alcohol -oxidation of the aldehyde to the ketone with PCC or PDC, the ketone will enolize as shown on the
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Unformatted text preview: product MANY answers were accepted, as long as it had a chance of working based on what we have learned One possible answer for 26-bromination of the alcohol with PBr3-displacement of the -Br with -CN using NaCN-selective reduction of -CN to CH2NH2 using LiAlH4-reductive amination to methylate this amine using HCHO followed by NaBH3CN-amide bond formation with the secondary amine with CH3COCl (or the anhydride)-reduction of NO2 to NH2 with H2, Pt-formation of the diazonium salt (from -NH2 to N2+) using HONO-substitution of N2+ with CH3COO- to give the product...
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This note was uploaded on 10/04/2010 for the course BIOL 200 taught by Professor Bureau during the Spring '06 term at McGill.

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2004FINAL_ANSWER - product MANY answers were accepted, as...

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