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)

Bonus question Identify the compound (C4H8O) that gives the following 1H NMR spectrum.

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?

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Predict the product for the following reaction.    

Consider the following spectrum of a carboxylic acid derivative. This spectrum indicates the presence of a ___________group.

What is the characteristic reaction of carboxylic acid derivatives?

Bonus question A compound with molecular formula C9H10O2 exhibits a triplet at d 1.2 (3H), a quartet at d 2.6 (2H), a doublet at d 7.3 (2H), a doublet at d 8.0 (2H) and a singlet at d 11 (1H) in its 1H NMR spectrum. Provide the IUPAC name of the structure that matches the above information.

Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.