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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

Chapter-9 covered a synthesis of alkynes by a double dehydrohalogenation of dihalides. A student tried to convert trans-2,5-dimethylhex-3-yne by adding bromine across the double bond and then doing a double elimination. The infrared and mass spectra of the major product are shown here.

  1. Do the spectra confirm the right product? If not, what is it?
  2. Explain the important peaks in the IR spectrum.

Question: A common lab experiment is the dehydration of cyclopentanol tocyclopentene.

a. Explain how you could tell from the IR spectrum whether your product was pure cyclopentene, pure cyclopentanol or a mixture of cyclopentene and cyclopentanol. Give approximate frequencies for distinctive peaks.

b. Explain why mass spectrometry might not be a good way to distinguish cyclopentene from cyclopentanol.

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

Question: (Another true story.) A student who was checking into her lab desk found an unlabeled sample from a previous student. She was asked to identify the sample. She did an IR spectrum and declared, “It looks like an alkane.” But it seemed too reactive to be an alkane, so she did a GC–MS. The mass spectrum is shown next. Identify the compound as far as you can, and state what part of your identification is uncertain. Propose fragments corresponding to the numbered peaks.

For each spectrum, interpret all the significant streching frequencies above 1580 cm-10

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