Author: Anonymous

Predict the product for the following reaction.       

Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic.

What is the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate?

Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

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.

Predict the product for the following reaction.           

Bonus question Identify the compound (C4H6O2) that gives the following 1H NMR spectrum.

Predict the product when cyclohexanone reacts with aqueous sodium hydroxide at 100°C.   

What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

Arrange the following indicated hydrogens in decreasing order (most to least) of acidity.