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Predict the product for the following reaction.      

Provide the reagents necessary to carry out the following conversion using a malonic ester synthesis.

Bonus question A compound with molecular formula C8H14O3 exhibits a triplet at d 1.0 (6H), a sextet at d 1.6 (4H) and a triplet at d 2.2 (4H) in its 1H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm-1. Provide the IUPAC name of the structure that matches the above information.

Predict the product(s) for the following reaction.  

Arrange the following compounds in order of increasing acidity.

Which of the following is a keto-enol tautomeric pair?

Give the IUPAC name of the structure that matches the following data: Molecular formula               C8H9NO IR absorption                        3328 and 1639 cm-1 1H NMR                                 2.95 ppm (singlet, 3H), 6.95 ppm (singlet, 1H), and 7.3-7.7 ppm (multiplet, 5H)

Which of the following carbonyl compounds does not undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

Bonus question Provide an efficient stepwise synthesis for the following.       The answer should be entered as in the following example: (this is an example!) 1. NaNH2   2. CH3CH2Br   3. H2, Lindlar’s Cat.    4. BH3, THF   5. H2O2, NaOH                          (Keep three spaces between each step) All chemicals and reagents  structures should be correct and with the proper sequence. No partial credit.

What are the hydrolysis products of the following reaction?