Question

1) Rank the following from the strongest acid to the weakest acid. Explain with reasons please.
A) CH3CH2OH
B) CH3OCH3
C) CH3—NH—CH3
D) CH3—C≡CH
E) CH3—CH=CH2

2) Draw all possible isomers that have the molecular formula C5H12O and name them using the systematic IUPAC name.

3) The following compound has 2 isomers. One isomer has a dipole moment of 0 D, whereas the other has a dipole moment of 2.95 D. Propose structures for the 2 isomers that are consistent with these data. ClCH=CHCl

Answer 1

(1)

Strong acid CH3CH2OH > CH3—C≡CH >  CH3—NH—CH3 >  CH3—CH=CH2 >  CH3OCH3 weakest acid

Explanation: If the compound has acidic proton (Hydrogen), then it is called as acidic compound

acidic hydrogen means, it has tendency to be released as H+ ion . So, if any H-atom is attached to another atom with higher electronegativity, that H-atom is a potential acidic H-atom. Oxygen is more electronegative element , so alcohol is more acidic than other compounds. Alkyne has SP Carbon where as Alkene has SP2 carbon. SP carbon is more electronegative than SP2 Carbon, so alkyne is more acidic than alkene. Protons on carbon are rarely the most acidic because carbon is not very electronegative. so CH3OCH3 is least acid

(2) molecular formula C5H12O has 6 chiral isomers and 5 achiral isomers( Total 11 isomers)