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Unformatted text preview: Name _______________________ Page 1 (F.06.215E1p1) I. (26 points) When Compound H is treated with dilute aqueous sodium hydroxide (NaOH/H 2 O), it is observed to give primarily Compound J . C O H 3 C H 3 C CH 2 CH 2 Cl NaOH H 2 O O C CH 2 CH 2 H 3 C CH 3 + NaCl + H 2 O Compound H Compound J (a) Provide the complete, step-wise mechanism for the formation of Compound J from Compound H under basic conditions. H O C CH 2 CH 2 H 3 C CH 3 (b) Give the IUPAC name for Compound H . (e) What is the structure of the product if Compound K is treated under the same reaction conditions? Clearly indicate the stereochemistry in your drawing. The molecular formula of the product is C 5 H 10 O. Na OH (c) How many absorption peaks would you expect to find in the hydrogen and carbon NMR spectra of Compounds H and J? Compound H Compound J number of peaks in H-NMR number of peaks in C-NMR (d) Another by-product that might be observed in this reaction is derived from an elimination reaction. What is the most likely anticipated structure of this elimination reaction by-product? C O H 3 C H 3 C CH 2 CH 2 Cl H C O H CH 3 CH 2 C Cl H CH 3 H NaOH H 2 O 6 6 2 2 2 2 3 3 Compound H Compound J Compound K C O H 3 C H 3 C CH 2 CH 2 Cl deprotonation mechanism = 2 alkoxide intermediate (Na+ optional) = 2 intramol substitution mechanism = 2...
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