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Chapter 13: Q 5. (page 501)

Question: What molecular ions would you expect for the compound depicted in the ball-and-stick model?

Short Answer

Expert verified

Answer

For the given compound, 162 and 164 molecular ions are expected.

Step by step solution

01

Identify the elements by analyzing the model

The tetravalent black ball symbolizes a carbon atom, the white ball symbolizes a hydrogen atom.

The red ball with only one bond, that is double the size of a carbon atom, must be a bromine atom.

02

Predicting the molecular ion

The molecular ion is predicted by calculating the molecular weight of the compound. A molecular ion is formed when a molecule experiences either the removal or addition of one/multiple electrons.

03

Determination of the molecular ions

The given molecular formula is C6H11Br. Bromine has two isotopes,79Br and 81Br.

The molecular weight is calculated below:

C6H1179Br  = 6×12+11×1+79×1=72+11+79=162

C6H1181Br  = 6×12+11×1+81×1=72+11+81=164

Hence, the molecular ions are 162 and 164.

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Most popular questions from this chapter

Question:Suppose you have two bottles, labeled ketone A and ketone B. You know that one bottle contains CH3CO(CH2)5CH3and one contains CH3CH2CO(CH2)4CH3but you do not know which ketone is in which bottle. Ketone A gives a fragment at m/z= 99 and ketone B givesa fragment at m/z= 113. What are the likely structures of ketones A and B from these fragmentation data?

Question: Match each compound to its IR spectrum.

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1.

a. Identify the structures of A and B.

b. Draw a mechanism for the conversion of citronellol to isopulegone.

c. Draw a mechanism for the conversion of isopulegone to B.

Question: Propose two molecular formulas for each of the following molecular ions: (a) 72; (b) 100; (c) 73.

Question:Benzonitrile (C6H5CN) is reduced to two different products depending on the reducing agent used. Treatment with lithium aluminum hydride followed by water forms K, which has a molecular ion in its mass spectrum at 107 and the following IR absorptions: 3373, 3290, 3062, 2920, and 1600 cm-1. Treatment with a milder reducing agent forms L, which has a molecular ion in its mass spectrum at 106 and the following IR absorptions: 3086, 2820, 2736, 1703, and 1600 cm-1. L shows fragments in its mass spectrum at m/z= 105 and 77. Propose structures for K and L and explain how you arrived at your conclusions.
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