Problem_Set_5A - 3 MgBr 2. H 3 O + 4. At room temperature,

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Chem 3580 - Spring 2009 Problem Set #5A 1. Acidic hydrolysis of tert -butyl acetate in H 2 18 O has been found to yield (CH 3 ) 3 C 18 OH and CH 3 COOH. Acidic hydrolysis of (S)-3,7-dimethyl-3-octyl acetate has been found to give (R)- 3,7-dimethyl-3-octanol with reduced optical activity and having the opposite sign of rotation. How do you interpret these results? 2. Supply the missing reagents and reaction conditions (a) — (d) for each transformation and write down the structure of A. OH CO 2 CH 3 O O O OH O COOH O CO 2 CH 3 (a) LiAlH 4 (reducing agent) (c) (d) (b) A 3. Give the structural formula for the compounds A-E Benzene + Succinic anhydride A (C 10 H 10 O 3 ) Zn[Hg] HCl B (C 10 H 12 O 2 ) SOCl 2 C (C 10 H 11 OCl) 1. AlCl 3 2. H 3 O + D (C 10 H 10 O) E (C 11 H 14 O) AlCl 3 1. CH
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Unformatted text preview: 3 MgBr 2. H 3 O + 4. At room temperature, N,N-dimethylacetamide gives three sharp singlets of equal intensity in the 1 H NMR spectrum. As the temperature is raised, two of the peaks (but not the third one) broaden and, finally at 110C, form one sharp peak. How do you account for this? What does it indicate about the structure of the amide? 5. Predict the product of -butyrolactone with (a) ammonia, (b) LiAlH 4 , (c) CH 3 CH 2 OH, H 2 SO 4 . 6. Starting from caproic acid, other organic reagents (containing no more than 4 carbon atoms) and any needed inorganic reagents outline a 3-step synthesis of 3-ethyl-3-octanol....
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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