Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 14, Problem 14.26P
Following is the mass spectrum of bromocyclopentane. The molecular ion m/z 148 is of such low intensity that it does not appear in this spectrum. Assign structural formulas for the cations of m/z 69 and 41.
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19.78 Write the products of the following sequences of reactions. Refer to your reaction road-
maps to see how the combined reactions allow you to "navigate" between the different
functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18
roadmaps along with your new Chapter 19 roadmap for these.
(a)
1. BHS
2. H₂O₂
3. H₂CrO4
4. SOCI₂
(b)
1. Cl₂/hv
2. KOLBU
3. H₂O, catalytic H₂SO4
4. H₂CrO4
Reaction
Roadmap
An alkene 5. EtOH
6.0.5 Equiv. NaOEt/EtOH
7. Mild H₂O
An alkane
1.0
2. (CH3)₂S
3. H₂CrO
(d)
(c)
4. Excess EtOH, catalytic H₂SO
OH
4. Mild H₂O*
5.0.5 Equiv. NaOEt/EtOH
An alkene 6. Mild H₂O*
A carboxylic
acid
7. Mild H₂O*
1. SOC₁₂
2. EtOH
3.0.5 Equiv. NaOEt/E:OH
5.1.0 Equiv. NaOEt
6.
NH₂
(e)
1. 0.5 Equiv. NaOEt/EtOH
2. Mild H₂O*
Br
(f)
i
H
An aldehyde
1. Catalytic NaOE/EtOH
2. H₂O*, heat
3. (CH,CH₂)₂Culi
4. Mild H₂O*
5.1.0 Equiv. LDA
Br
An ester
4. NaOH, H₂O
5. Mild H₂O*
6. Heat
7.
MgBr
8. Mild H₂O*
7. Mild H₂O+
Li+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water?
Group of answer choices
LiBr
LiI
LiF
LiCl
Q4: Write organic product(s) of the following reactions and show the curved-arrow mechanism
of the reactions.
Br
MeOH
OSO2CH3
MeOH
Chapter 14 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 14.2 - Calculate the nominal mass of each ion. Unless...Ch. 14.3 - Propose a structural formula for the cation at m/z...Ch. 14.3 - The low-resolution mass spectrum of 2-pentanol...Ch. 14 - Draw acceptable Lewis structures for the molecular...Ch. 14 - The molecular ion for compounds containing only C,...Ch. 14 - For which compounds containing a heteroatom (an...Ch. 14 - The so-called nitrogen rule states that if a...Ch. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Determine the probability of the following in a...Ch. 14 - The molecular ions of both C5H10S and C6H14O...Ch. 14 - Prob. 14.13PCh. 14 - Carboxylic acids often give a strong fragment ion...Ch. 14 - For primary amines with no branching on the carbon...Ch. 14 - Prob. 14.16PCh. 14 - A characteristic peak in the mass spectrum of most...Ch. 14 - Predict the relative intensities of the M and M +...Ch. 14 - The mass spectrum of compound A shows the...Ch. 14 - The mass spectrum of compound B, a colorless...Ch. 14 - Write molecular formulas for the five possible...Ch. 14 - Write molecular formulas for the five possible...Ch. 14 - The molecular ion in the mass spectrum of...Ch. 14 - Prob. 14.24PCh. 14 - Following is the mass spectrum of 1-bromobutane....Ch. 14 - Following is the mass spectrum of...Ch. 14 - Following is the mass spectrum of an unknown...Ch. 14 - Following is the mass spectrum of...Ch. 14 - Prob. 14.29PCh. 14 - Following are mass spectra for the constitutional...Ch. 14 - 2-Methylpentanal and 4-methyl-2-pentanone are...Ch. 14 - Prob. 14.32PCh. 14 - Account for the presence of the following peaks in...Ch. 14 - All methyl esters of long-chain aliphatic acids...Ch. 14 - Propylbenzene, C6H5CH2CH2CH3, and isopropyl...Ch. 14 - Account for the formation of the base peaks in...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38P
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