Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 13, Problem 13.34P
only one of these isomers gives a significant fragment at
peak at
the mass spectrum of the other isomer occurs at
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2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?
1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F.
(i) Draw the structure of F.
(ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F.
(ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose
the structures of these two fragments.
(iv) Draw the resonance structure for each of the cation in (iii).
A compound gives a mass spectrum with essentially only three peaks at m/z = 77 (40%), 112 (100%), and 114 (33%). Identify the compound.
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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- (a) Based on the mass spectrum shown below, 100 73 LOH 80 - A 58 20 - 100 10 20 30 40 50 60 70 80 90 100 110 m/z (i) identify the molecular ion peak of compound A. (ii) explain how the labelled fragments are formed. Relative Intensityarrow_forwardPropose a molecular formula for a compound that exhibits the following peaks in its mass spectrum. (M)+• at m/z = 68, relative height = 100% (base peak) (M+1)+• at m/z = 69, relative height = 4.3%arrow_forwardA compound used as a moth repellant has three molecular ion peaks at m/z = 146 (100%), 148 (65%) & 150 (10%) amu in its mass spectrum. A pair of smaller peaks are seen at m/z= 111 (34%) & 113 (11%). The infrared spectrum shows sharp absorption just above 3000 cm^-1 region, and also at 1480 cm^-1. The ^1 H nmr shows a single sharp signal at delta = 7.2 ppm, and the ^13 C nmr has two signals (delta = 133 & 130 ppm).arrow_forward
- (a) A compound with molecular formula C12H2408 gave 8 = 3.66 ppm a single (for peak at 'H-NMR) and 8= 70-91 ppm (for 13C). The 13C peak was inverted under DEPT considerations. Predict the molecular structure and assign values.arrow_forwardAlthough 2,2-dimethylhexane has a molecular weight of 114, no peak is observed at m/z = 114. The base peak in the mass spectrum occurs at M-57 (a) Draw the fragmentation responsible for the formation of M-57 ion (b) Explain why this cation is the most abundant ion to pass through the spectrometer. (c) Explain why no molecular ion survive long enough to be detected. (d) Can you offer an explanation as to why M-15 peak is not the base peak?arrow_forwardThe mass spectrum of the following compound shows fragments at m/z= 127, 113, and 85. Propose structures for the ions that give rise to thesepeaks.arrow_forward
- A (a) Draw the structures of the species that correspond to each of the peaks A-E in the following mass spectrum of heptane. (b) Identify the M* peak, the M + 1 peak, and the base peak. 100 80 – 60 40 20 D 20 40 60 80 100 120 m/z Relative abundancearrow_forwardThe mass spectrum of an alcohol (C5H12O) exhibits a base peak at m/z =59. Is the alcohol most likely pentan-1-ol, pentan-2-ol, or pentan-3-ol? Explain.arrow_forwardPropose a molecular formula for a compound that exhibits the following peaks in its mass spectrum Problem 1: (M)+• at m/z = 72, relative height = 38.3% of base peak; (M+1)+• at m/z = 73, relative height = 1.7% of base peakarrow_forward
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