Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 13, Problem 13.38P
A low-resolution mass spectrum of the neurotransmitter dopamine gave a molecular ion at
Two possible molecular formulas for this molecular ion are
resolution mass spectrum provided an exact mass at
formulas is the correct one?
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In the mass spectrum of an unknown organic
compound, the molecular ion had a relative
abundance of 19.0 while the M+1 had a relative
abundance of 1.5.
Estimate the number of carbons in the molecule.
1
4
7
2
LO
5
8
carbons
3
6
9
X
C
14. Shown below are the mass spectra (without data tables) of four molecules. (The structure of each
molecule is shown on the spectrum.)
Mark the [M] peak for each, and indicate the molecular weight of the molecule.
Relative Intensity
Relative Intensity
100
80
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0-mm
10
100-
80
a.
20-
115-14-5501
0-mm
10
20
b.
=0
20
30
30
40
40
50
50
60
m/z
60
m/z
70
70
80
80
90
100
90 100
Relative Intensity
Relative Intensity
100-
80
40
20
0
100
80
40
10
20-
15-NU-5580
15 20 25
115--555
ont
10
20
30
30
35 40 45 50 55
m/z
40
50
m/z
60
60
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65 70 75
80
Based on the five mass spectra you have seen, describe how one might identify the [M]*
peak (molecular ion peak) on the mass spectrum of an unknown compound.
2clar
ISTRY EXAM
A Chemistry student performed an experiment on the preparation and identification of an ester. He was given
solutions of a carboxylic acid and an alcohol. He then prepared the ester as per laboratory instruction and
identified the odour of the ester as a pear flavour.
A carboxylic acid has empirical formula CH,O, and its structure is determined by using various spectroscopic
techniques.
(a) The mass spectrum for this carboxylic acid molecule is given below.
100-
80-
60-
relative
intensity
40-
20-
10 15 20 25 30 35 40 45 50 55 60 65 70 75
mass/charge (m/e)
(i) State the relative molecular mass of this molecule; hence determine its molecular formula.
(ii) Draw the structural formula of the carboxylic acid and give its systematic name.
ark
(b) Use the information provided by its Infrared spectrum below to answer the following questions
100
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Use the following information to propose a...Ch. 13 - Prob. 13.4PCh. 13 - What molecular ions would you expect for the...Ch. 13 - The mass spectrum of 2,3-dimethylpentane also...Ch. 13 - The base peak in the mass spectrum of 2, 2,...Ch. 13 - (a) What mass spectral fragments are formed by ...Ch. 13 - What cations are formed in the mass spectrometer...Ch. 13 - The low-resolution mass spectrum of an unknown...
Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...Ch. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - Problem 13.17 How do the three isomers of...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Problem-13.21 Which of the following possible...Ch. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - Prob. 13.25PCh. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Problem-13.29 What is the molecular formula for...Ch. 13 - Problem-13.30 Propose a molecular formula for rose...Ch. 13 - 13.31 Match each structure to its mass spectrum
Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.34 and have the same molecular ion in the...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.36PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - 13.41 Which of the highlighted bonds absorbs at...Ch. 13 - 13.42 What major IR absorptions are present above ...Ch. 13 - 13.43 How would each of the following pairs of...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - 13.45 Reduction of cyclohex-2-enone can yield...Ch. 13 - Prob. 13.46PCh. 13 - 13.47 Match each compound to its IR spectrum
Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.53PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.56PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.60PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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- You have conducted an experiment where you obtained 22.4g ZnCl2. The accepted value is 22.7g. What is the error and relative (%) error?arrow_forwardA compound containing only carbon, nitrogen, oxygen, and hydrogen contains four carbon atoms. If the M+ peak in its mass spectrum appears at m/z = 87, then how many nitrogen atoms does it contain?arrow_forwardBy knowing the natural abundance of minor isotopes, it's possible to calculate the relative heights of M+ and M+1 peaks. If natural abundances are 12C - 98.9% and 13C - 1.10%, what are the relative heights, to the nearest 0.1%, of the M+ and M+1 peaks in the mass spectrum of benzene, C6H6? Ignore the contributions of isotopes like 2H (deuterium; 0.015% natural abundance) and 17O (0.04% natural abundance) that are small.The relative heights are, in order of increasing mass: 100 to ____arrow_forward
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