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Chapter 12: Q.17P (page 637)

Predict the masses and the structures of the most abundant fragments observed in the mass spectra of the following compounds

a. 2-methylpentane

b. 3-methylhex-2-ene

c. 4-methylpentane-2-ol

d. 2-methyl-1-phenylpropane

e. Cyclohexylisopropy; ether [cyclohexyl--O-CH(CH3)2 ]

f. CH3CH2CH2NHC(CH3)2

g.

h.3-bromo-2-methylpentane

Short Answer

Expert verified

Answer

The most abundant peaks for all the given species and their formation through fragmentation is shown.

Step by step solution

01

Introduction

Molecular mass of a compound is given mz (mass to charge) value of the molecular ion in the mass spectrum.

M+e-→M++2e-

02

 Step 2: Explanation and answer of the given subparts

(a)

(b)

(c)


(d)

(e)

(f)

(g)

(h)

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Most popular questions from this chapter

Question: A C-D (carbon–deuterium) bond is electronically much like a C-H bond, and it has a similar stiffness, measured by the spring constant, k. The deuterium atom has twice the mass (m) of a hydrogen atom, however.

(a) The infrared absorption frequency is approximately proportional tokm , when one of the bonded atoms is much heavier than the other, and m is the lighter of the two atoms (H or D in this case). Use this relationship to calculate the IR absorption frequency of a typical C-D bond. Use as a typical C-H absorption frequency.

(b) A chemist dissolves a sample in deuterochloroform (CDCl3) and then decides to take the IR spectrum and simply evaporates most of theCDCl3 . What functional group will appear to be present in this IR spectrum as a result of theCDCl3 impurity?

Complete the following conversion table:

v(cm-1)

4000

1800

1670

1620

400

λ(μm)

2.50

3.40

3.13

4.87

25.0

Three IR spectra are shown, corresponding to three of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen.

Question: (A true story.) While organizing the undergraduate stockroom, a new chemistry professor found a half-gallon jug containing a cloudy liquid (bp 100–105 °C), marked only “STUDENT PREP.” She ran a quick mass spectrum, which is printed below. As soon as she saw the spectrum (without even checking the actual mass numbers), she said, “I know what it is.”

(a) What compound is the “student prep”? Any uncertainty in the structure?

(b) Suggest structures for the fragments at 136, 107, and 93. Why is the base peak (at m/z 57) so strong?


Question: Four infrared spectra are shown, corresponding to four of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen
See all solutions

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