Question

Unknown A esterification mw ill then while 5.5 5.0 4.5 4.0 3.5 3.0 2.5 . 2.00 3.69 1.46 7.09

Esterification of an Unknown C5 alcohol using DAMP catalyst -

a) interpret the 1H-NMR of your unknown C7 acetyl ester and identify the structure of the original C5 alcohol. Your ester has seven carbons in its ester, two from the acetic anhydride and five from the original alcohol.

b) draw the 8 constitutional isomers of the unknown alcohol with the molecular formula C5H12O. You should ignore stereoisomers.

Answer 1

Unknown A الابرياء العالم B CH2 Hydrogens 2H SO 45 40 25 3.0 C CH Hydrogen 1H D CH2 Hydrogens 2H СН о CH3-CH2-CH-CH2-O-C-CH3 A B C D E E CH3 Hydrogens 3H A CH3 Hydrogens 6H Answer original alcohol _ CH3 CH3-CH2-CH-CH2-OH CHICHCHCH.CH Reaction 0 0 CH3 CH3-CH2-CH-CH2-OH + H2C0 CH3 o an overal en CH3 0 CH3-CH2-CH-CH2-O-C-CH3 ester CH3 CH3-CH2-CH-CH2-OH original alcohol isomers CH3 CH3 CH3-CH2-CH2-CH-OH pentan-2-01 CH3 CH3-CH-CH2-CH2-OH 3-methylbutan-1-01 CH3-CH2-CH2-CH2-CH2-OH pentan-1-01 CH3-CH2-CH-CH2-OH 2-methylbutan-1-01 CH3 CH3-C-CH2-OH CH3 CH3-CH-CH-OH CH3 3-methylbutan-2-01 - CH3 CH3 CH3-CH2-C-OH CH3 2-methylbutan-2-01 OH CH3-CH2-CH-CH2-CH3 2,2-dimethylpropan-1-ol pentan-3-01