A compound

(C_(6)H_(12)O_(2))

has the following

^(1)H

NMR spectrum ; solvent

{

(

:=CDCl_(3))

} :\

\\\\delta 3.7ppm

(singlet,

3H

),

\\\\delta 2.3ppm

(sextet,

1H

),

\\\\delta 1.8ppm

(quintet,

2H

),

\\\\delta 1.1ppm

(doublet,

3H

), and

\\\\delta 0.9ppm

(triplet,

3H

Recall that a sextet is a 6-peak multiplet and a quintet is a 5-peak multiplet, a triplet is a 3-peak multiplet, and a doublet is a 2-peak multiplet.\ This compound has a strong, sharp absorption at

1740cm^(-1)

in its infrared (IR) absorption spectrum.\ (a) [3 points] What is the index of

H_(2)

deficiency for this compound?\ (b) [6 points] Give the most reasonable structural formula for this compound. Clearly label with a letter each set of Hs in your proposed structural formula. Make a table that gives a letter for each set of

Hs

and the corresponding numerical value of the chemical shift (

\\\\delta

) in units of ppm.\ (c) points

A compound (C6H12O2) has the following 1H NMR spectrum (300MHz; solvent =CDCl3) : 3.7ppm (singlet, 3H ), 2.3ppm (sextet, 1H ), 1.8ppm (quintet, 2H ), 1.1ppm (doublet, 3H ), and 0.9ppm (triplet, 3H Recall that a sextet is a 6-peak multiplet and a quintet is a 5-peak multiplet, a triplet is a 3-peak multiplet, and a doublet is a 2-peak multiplet. This compound has a strong, sharp absorption at 1740cm1 in its infrared (IR) absorption spectrum. (a) [3 points] What is the index of H2 deficiency for this compound? (b) [6 points] Give the most reasonable structural formula for this compound. Clearly label with a letter each set of Hs in your proposed structural formula. Make a table that gives a letter for each set of Hs and the corresponding numerical value of the chemical shift () in units of ppm. (c) [3 points] How many peaks are there in the proton-decoupled 13C NMR spectrum of this compound? (d) [3 points] To which family (functional group class) of organic compounds does compound A belong