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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-鈫�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

The mass spectrum of n-octane shows a prominent molecular ion peak (m/z 114). There is also a large peak at m/z 57, but it is not the base peak. The mass spectrum of 3,4-dimethylhexane shows a smaller molecular ion, and the peak at mass 57 is the base peak. Explain these trends in abundance of the molecular ions and the ions at mass 57 and predict the intensities of the peaks at masses 57 and 114 in the spectrum of 2,2,3,3-tetramethylbutane.

Question: (A true story.) While organizing the undergraduate stockroom, a new chemistry professor found a half-gallon jug containing a cloudy liquid (bp 100鈥�105 掳C), marked only 鈥淪TUDENT PREP.鈥� 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, 鈥淚 know what it is.鈥�

(a) What compound is the 鈥渟tudent prep鈥�? 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?

These five structures all have distinguishing absorption in the IR. Match each structure with its characteristic absorption.

Structure 1

Structure 2

Structure 3

Structure 4

Structure 5

(a)sharp, 2254 cm-1 (b) very broad, centered about3330cm-1 (c) strong, slightly broadened, 1645cm-1 (d) broad with spikes at 3367cm-1and 3392cm-1(e) strong, sharp 1717cm-1


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

Question:Identify which of these four mass spectra indicate the presence of sulfur, chlorine, bromine, iodine, or nitrogen. Suggest a molecular formula for each.
See all solutions

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