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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 110°C, 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 γ-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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