From the list below, pick the compound that does not react with acetyl chloride.

A compound with molecular formula C6H12O2 exhibits two singlet in its 1HNMR spectrum, at δ 1.4 (9H) and δ 2.0 (3H). Its IR spectrum shows a strong absorption band near 1740 cm-1. What is the structure for this compound?

Predict the product for the following reaction.  

Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

Predict the product for the following reaction.  

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.

Identify the keto form of the following enol.  

Provide the reactants necessary to prepare the following compound using Robinson annulation.      

Which of the following is the aldol addition product of butanal?

A compound with molecular formula C8H14O4 exhibits a triplet at δ 1.3 (I=6), a singlet at δ 2.6 (I=4) and a quartet at δ 4.2 (I=4) in its 1HNMR spectrum. Its IR spectrum shows a strong absorption band near 1740 cm-1. What is the structure for this compound?