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POD14Key - 2 in acetic acid solvent Compounds A B C and D...

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Problem of the Day #14 Answer Key Deadline : IN CLASS on Tu 8/3/2010 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Each box is worth 5 points. Compound A , having molecular formula C 4 H 7 BrO 2 , has the IR and 1 H NMR spectra given below. 13 C NMR data is listed below the IR spectrum: When A is exposed to aqueous potassium hydroxide, followed by dilute aqueous acid, Compound B (C 3 H 5 BrO 2 ) is formed. When B is treated with SOCl 2 , Compound C (C 3 H 4 BrClO) is produced. When C is reacted with (CH 3 CH 2 ) 2 CuLi, Compound D (C 5 H 9 BrO) is formed. D is also formed when 3- pentanone is treated with Br
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Unformatted text preview: 2 in acetic acid solvent. Compounds A , B , C , and D are chiral, and each is isolated as a racemic mixture of enantiomers. Propose structures for Compounds A , B , C , and D by completing the reaction scheme given below. It is not necessary to show stereochemistry in the structures that you draw, nor is it necessary to explain your answers. A B C D 1) KOH, H 2 O 2) H 3 O + SOCl 2 (CH 3 CH 2 ) 2 CuLi Br 2 , CH 3 CO 2 H O 3-Pentanone O Br Cl O Br OH O Br OCH 3 O Br 1H quartet 3H singlet 3H doublet 13 C NMR : 170.7, 52.9, 39.8, 21.7...
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