3. A chemist wants to make the following compound, but is unsure how to do this. Given your excellent education at Valpo, you think carefully about this and decide that you probably can propose a way of making this compound via a substitution reaction. Propose starting materials and solvent for the necessary reaction. NH

Please explain the chosen letter. In the sequence of reactions below, A and B are which of the following? o NaCN, (HCl) H3O+ →B (CH3),CO- A- A а. (CН3)2C(ОН)CN, (CH3)2C(ОH)соон b. (CH3)2C(ОН)CN, (CH3)2C (ОН)2 с. (CНз)2C(ОH)CN, (CH3)2CHCOОН d. (CH3)2C(OH)CN, (CH3)2C=O

The dehydration of compound A produces many different products. One of the products formed is compound G. Can you figure out the mechanism? The mechanism proceeds through five intermediates (compounds B-F). Sort the intermediates according to the reaction mechanism which includes a methyl shift, a hydride shift and a resonance structure. Note: treat resonance structures as individual steps. Compound III Compound IV Compound II Compound I Compound V Your answer compound A OH compound G intermediates II

4. As shown below, compound 2 can be made from compound 1 in two steps. Provide the reagents, A, and draw the product B for the first step. Then, provide the reagents C that lead to the final product. (Hint: Product B has a peak in its 'H NMR spectrum at 11.1 ppm that integrates to 1H.) 1 OH A C B