850SurveryExamKey - KEY Question 1 (20 points, 2 points...

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Unformatted text preview: KEY Question 1 (20 points, 2 points each box): Fill in the boxes with the appropriate missing reagents. NH2 Hofmann Elimination Question 2 (20 points): Outline an efficient synthesis for the following Robinson annulation synthesis, starting with the given starting material and any suitable reagents. 0 if T V) H i If“! ‘\./ A0 :9 Question 3 (20 points, 2 points each box): Fill in the boxes with the appropriate reactants, reagents or products. For the products, only draw the major organic products. Note: Make sure to show stereochemistry where applicable. a) H2 CEO-0H3 —-——> Lindlar cat. b) U —————-—> Stereochemistry 0) QH ' 1)socb ———~> 2) H3C—CECNa d) NH2 1) NaNOz, H2304, H20 —————————> 2) H20, heat O 1) ———————> > 2) H30+ NaBH4, Ethanol | .__————> O 0 g) NaOH ph ———————> Ph D 1. SOCI2 ————-> 2. AICI3 0 Question 4 (10 points): Use the designations below to best describe the following pairs of compounds. E = enantiomers, D = diastereoisomers, I = Identical and C = constitutional isomers, N = neither, Q Q OH >43 HOS OH HO OH HHOH Ho OH O COZH CH3 COZH CH3 HOAIIH HOan XIIH CH3 COZH “0 CH3 COzH MCI nu. Question 5 (10 points): Estimate the pKa values (:1 pKa unit) of the following compounds and write the value in the box below the corresponding compounds. O O ° Q )% ___I O : 1-1,: NH4+ N; l : ill Question 6 (20 points): Provide a reasonable synthesis for the following molecules using the given starting material and anything else you need. Several steps are required. O ———> O/\ ————> ————> /NH / CHick /J knmoéi C51” /f // ,2 c, 7 » o x *4 “u C —°~~ / V T HIM/5 L j A {\(27 A HMO; / ’C "571 (065% ’V H ‘ CC E} M V, ’ (A / / ( M /c w "Mr M}! / ...
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This note was uploaded on 09/22/2008 for the course CEM 850 taught by Professor Borhan during the Spring '05 term at Michigan State University.

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850SurveryExamKey - KEY Question 1 (20 points, 2 points...

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