Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Question
Chapter 13, Problem 13.32P
Interpretation Introduction
Interpretation: The likely structures of
Concept introduction: Molecular ion is the radical cation which is formed by ejection of electrons from a molecule when a beam of high-energy electrons are bombarded on a molecule.
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Q3: Curved Arrows, Lewis Acids & Bases, Nucleophiles and Electrophiles
Considering the following reactions:
a) Predict the products to complete the reactions.
b) Use curved electron-pushing arrows to show the mechanism for the reaction in
the forward direction. Redraw some of the compounds to explicitly illustrate all
bonds that are broken and all bonds that are formed.
c) Label Lewis acids and bases, nucleophiles and electrophiles in the reactions.
A.
S
+
AICI 3
B.
+
H₂O
3. A thermometer is placed in a test tube of chipped ice at -5.0 °C. The temperature is recorded at the
time intervals shown below until room temperature is reached. Plot the data given below on graph
paper and explain all flat, horizontal portions of the curve. Plot time on the X-axis!
Time (min)
Temperature (°C)
0
-5.0
2
-2.5
4
-1.0
6
0.0
10
0.0
15
0.0
20
0.0
25
0.0
30
1.5
35
4.0
40
8.0
45
11.5
50
15.0
55
17.5
60
19.0
65
20.0
70
20.0
75
20.0
80
20.0
Naming the Alkanes
a) Write the IUPAC nomenclature of the compound below
b) Draw 4-isopropyl-2,4,5-trimethylheptane, identify the primary, secondary, tertiary, and
quaternary carbons.
c) Rank pentane, neopentane and isopentane for boiling point.
pentane:
H3C-CH2-CH2-CH2-CH3
neopentane:
CH3
H3C-Ċ-CH3
I
CH3
isopentane:
CH3
H3C-CH2-CH-CH3
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Prob. 13.3PCh. 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. 13.11PCh. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - How do the three isomers of molecular formula...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 - Prob. 13.20PCh. 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 - What molecular ion is expected for each compound?Ch. 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 - Match each structure to its mass spectrum. a. b....Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.32PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - Can the exact mass obtained in a high-resolution...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 - Which of the highlighted bonds absorbs at higher v...Ch. 13 - What major IR absorptions are present above...Ch. 13 - How would each of the following pairs of compounds...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - Prob. 13.42PCh. 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. 13.49PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.52PCh. 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. 13.56PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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