058-RG5-ProbSol-10 - Page 2 LEARNING STRATEGIES CENTER...

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Chem 1058 J. Walcott LEARNING STRATEGIES CENTER Spring 20010 Review Guide #5 Supplemental Problems Solutions 1. Check answers in the Solutions Manual. 2. Synthesize 2-phenyethanoic acid from benzene without using the coupling reactions. OH O FeBr 3 Br 2 Br 1. Mg, ether 2. 3. H 3 O + O OH Na 2 Cr 2 O 7 H 2 SO 4 The synthesis requires the addition of two carbons, which can be accomplished by the reaction of a Grignard reagent with an oxirane (ethylene oxide). 3. Write a mechanism of the reaction between p -hydroxyaniline and acetic anhydride in NaOH and water to prepare acetaminophen. NH 2 N H HO CH 3 H 3 C O O C C CH 3 O C H 3 C C HO CH 3 H 3 C O C C H H OH N HO CH 3 H 3 C O C C H N HO deprotonation by hydroxide O O O O H 2 O Acetaminophen
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Chem 1058
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Unformatted text preview: Page 2 LEARNING STRATEGIES CENTER Spring 2010 4. How would you synthesize (N,N-dimethylaminomethyl)cyclohexane from bromocylohexane? The product is an N-substituted amine, which can be formed by reduction of an amide. The amide results from a reaction of an acid chloride with an amine. The acid chloride results from the reaction of SOCl 2 with a carboxylic acid that is formed by carboxylation of the Grignard reagent synthesized from the starting material. Br MgBr O C N(CH 3 ) 2 NaOH (CH 3 ) 2 NH O C Cl SOCl 2 C O OH Mg, ether 1. CO 2 , ether 2. H 3 O Br CH 2 N(CH 3 ) 2 ?...
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This note was uploaded on 04/05/2010 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

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058-RG5-ProbSol-10 - Page 2 LEARNING STRATEGIES CENTER...

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