Question

I've been given the formula C5H12O. I need to determine the structure and IUPAC name by looking at the IR, proton NMR, and carbon NMR.

Answer 1

Alcohol isomers : 
(1) CH3CH2CH2CH2CH2OH = n-pentanol (pentane-1-ol) 
(2) CH3CH2CH2CH(OH)CH3 = 2-pentanol (pentane-2-ol) 
(3) CH3CH2CH(OH)CH2CH3 = 3-pentanol (pentane-3-ol) 
(4) CH3CH2CH(CH3)CH2OH = 2-methyl-1-butanol 
(5) CH3CH2C(CH3)(OH)CH3 = 2-methyl-2-butanol 
(6) CH3CH(OH)CH(CH3)CH3 = 3-methyl-2-butanol 
(7) CH2(OH)CH2CH(CH3)CH3 = 4-methyl-1-butanol 
(8) CH3CH(CH3)CH2CH2OH = 3-methyl-1-butanol 
(9) CH3C(CH3)2CH2OH = 2,2-dimethyl-1-propanol 

Ether isomers: 
(1) CH3CH2CH2CH2-O-CH3 = methyl butyl ether 
(2) CH3CH2CH2-O-CH2CH3 = ethyl propyl ether 
(3) CH3CH(CH3)CH2-O-CH3 = methyl isobutyl ether 
(4) CH3CH2CH(CH3)-O-CH3 = methyl sec-butyl ether 
(5) CH3CH2-O-CH(CH3)CH3 = methyl isopropyl ether