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(CHEM 3603) Organic Chemistry 1, Summer Session Problems Set # 2, Chapters 8-10 L. Propose the best synthetic route to do the following transformation. Draw clearly the different intermediates indicating their stereochemistry if present. (More than one step is needed) 0% 2. Propose a complete and detailed mechanism for the products in the following reaction. 2. CH CH2OH H and heat Propose a synthetic route to produce the following alkyl halides from the starting material given. And draw the complete mechanism for the synthesis. (Hint: Consider the possibility of rearrangements and remember you can use any reagents or new substrates as necessary). 3. Br -cha 4. Devise a stepwise mechanism for the following reaction. CH.CH-ONa + C Ci Draw the products of the following reaction, indicating the stereochemistry where appropriate. Also draw the stepwise mechanism 5. 6 Propose a synthetic route for the following conversion from the alkyl halide to the alcohol. Keep track of the stereochemistry in every step. (Hint: more than one step is required, and a trisubstituted alkene is praduced during the synthesis to get to the final product) CI 7. Propose a synthesis for the conversion of the tertiary alcohol to the diol given in the reaction below. (Hint: a secondary alcohol might be produced in the synthesis before reaching the final diol. Draw all the mechanisms involvedhelp please!

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