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ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Question
Chapter 14, Problem 35P
Interpretation Introduction
Interpretation:
A splitting diagram for vicinal protons in the given molecule is to be constructed and the coupling constants
Concept introduction:
The size of the vicinal coupling constant between trans protons on a double bond is normally larger than that between cis protons.
For the compounds in which vicinal protons are not equivalent, a proton
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206 Pb
82
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VAΣ
ΜΕ ΑΣΦ
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Previous Answers
?
protons, neutrons
Please draw the inverted chair forms of the products for the two equilibrium reactions
shown below. Circle the equilibrium reaction that would have a AG = 0, i.e., the relative energy of
the reactant (to the left of the equilibrium arrows) equals the relative energy of the product? [No
requirement to show or do calculations.]
CH3
CH3
HH
CH3
1
-CH3
5.
Please consider the Newman projection of tartaric acid drawn below as an eclipsed
conformer (1). Please draw the most stable conformer and two intermediate energy conformers
noting that staggered conformers are lower in energy than eclipsed forms even if the staggered
conformers have gauche relationships between groups. [Draw the substituents H and OH on the front
carbons and H, OH and CO₂H on the back carbons based on staggered forms. -CO₂H is larger than -OH.]
OH
COH
ICOOH
COOH
COOH
1
2
COOH
COOH
3
4
Staggered
Staggered
Staggered (most stable)
Indicate the number of each conformer above (1, 2, 3 and 4) that corresponds to the relative energies
below.
Ref=0
Rotation
6. (60 points)
a. Are compounds 1 and 2 below enantiomers, diastereomers or identical?
OH
OH
HO
HO
LOH
HO
HO
OH
2
OH
OH
b. Please complete the zig-zag conformation of the compound
(3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes.
3.
Chapter 14 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 14.3 - Prob. 1PCh. 14.3 - Prob. 2PCh. 14.4 - The 1H NMR signal for bromoform (CHBr3) appears at...Ch. 14.5 - identify the most shielded and least shielded...Ch. 14.5 - (a) Assign the chemical shifts 1.6, 2.2, and 4.8...Ch. 14.5 - Assign the chemical shifts 1.1, 1.7, 2.0, and 2.3...Ch. 14.5 - Assign the chemical shifts 1.6, 4.0, 7.5, 8.2, and...Ch. 14.6 - The 300-MHz 1H NMR spectrum of 1,4-dimethylbenzene...Ch. 14.6 - Prob. 9PCh. 14.6 - How many signals would you expect to find in the...
Ch. 14.7 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.8 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.11 - Prob. 13PCh. 14.11 - Prob. 14PCh. 14.12 - Hydrogen bonding between the oxygen of dimethyl...Ch. 14.14 - Prob. 16PCh. 14.15 - The 13C NMR spectrum of 1-bromo-3-chloropropane...Ch. 14.15 - Consider carbons x, y, and z in p-methylanisole....Ch. 14.15 - Prob. 19PCh. 14.16 - To which of the compounds of Problem 14.16 does...Ch. 14.18 - DEPT spectra for a compound with the formula...Ch. 14.20 - Vibrational frequencies are sensitive to isotopic...Ch. 14.21 - Prob. 23PCh. 14.22 - Prob. 24PCh. 14.23 - Prob. 25PCh. 14.23 - Which one of the C5H8 isomers shown has its max at...Ch. 14.24 - Knowing what to look for with respect to isotopic...Ch. 14.24 - The base peak appears at m/z105 for one of the...Ch. 14.24 - Mass spectra of 1-bromo-4-propylbenzene and...Ch. 14.25 - Prob. 30PCh. 14 - Each of the following compounds is characterized...Ch. 14 - Deduce the structure of each of the following...Ch. 14 - From among the isomeric compounds of molecular...Ch. 14 - The H1NMR spectrum of fluorene has signals at 3.8...Ch. 14 - Prob. 35PCh. 14 - H1NMR spectra of four isomeric alcohols with...Ch. 14 - Prob. 37PCh. 14 - We noted in Section 14.13 that an NMR spectrum is...Ch. 14 - Identify each of the C4H10O isomers on the basis...Ch. 14 - A compound (C3H7ClO2) exhibited three peaks in its...Ch. 14 - Label nonequivalent carbons in the following...Ch. 14 - Compounds A and B are isomers of molecular formula...Ch. 14 - C13 NMR spectra for four isomeric alkyl bromides...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Identify the C3H5Br isomers on the basis of the...Ch. 14 - Prob. 47PCh. 14 - A compound (C8H10O) has the IR and H1NMR spectra...Ch. 14 - Deduce the structure of a compound having the...Ch. 14 - Figure 14.53 presents IR, H1NMR, C13NMR and mass...Ch. 14 - H1NMR, C13NMR, IR, and mass spectra are shown for...Ch. 14 - 1H NMR and IR spectra for a compound with the...Ch. 14 - FriedelCraftsalkylation of benzene with...Ch. 14 - Prob. 54DSPCh. 14 - Prob. 55DSPCh. 14 - Prob. 56DSPCh. 14 - Prob. 57DSPCh. 14 - Prob. 58DSP
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