Academic Integrity: tutoring, explanations, and feedback — we don’t complete graded work or submit on a student’s behalf.

lem III. Structure Determination (20 points). High resolution mass spectral anal

ID: 706335 • Letter: L

Question

lem III. Structure Determination (20 points). High resolution mass spectral analysis of a pure sample of compound F reveals it to have a molecular formula of ChOOC. ,H NMR analysis of a sample dissolved in CDC yieids the following spectrum. The numbers above each signal represent integration values for the area under the signal. 35.7 ? 23.1 23.3 230 4 13 13 IJ 3.5 3.0 2.5 2.0 (i) Draw a Lewis structure for compound F consistent with the data provided above (i) For each chemical shift, draw an arrow pointing to one of the hydrogens that gives rise to that signal.

Explanation / Answer

Integeration of hydrogen give value = 23, 23.1 ,35.7, 23.3

On simplification give = 2,2,3,2 hydrogen total of 9 hydrogen.

Molecular formula = C5H9OCl

Index of Hydrogen deficiency = 5 - (9/2) - (1/2) = 0

It means no double bond or ring is there.

Structure = CH3-CH2-O-CH2-CH2Cl

Singlet. Quad. Trip . triplet

2.2. 2.0. 3.6 . 2.65