14. Which of the following would you expect to have the lowest boiling point? (A) CH3CH2OH (B) CH3CO2H (C) CH3CH2OCH2CH3 (D) (CH3CH2)2NH (E) (CH3CH2)3N

13. A mixture of oct-1-yne, oct-2-yne, and oct-3-yne was hydrogenated in the presence of a platinum catalyst until hydrogen uptake ceased. If one assumes that the hydrogenation went to completion, how many different eight-carbon hydrocarbons were produced? (A) 1 (B) 2 (C) 3 (D) 6 (E) 8