ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
12th Edition
ISBN: 9781119766919
Author: Solomons
Publisher: WILEY
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Textbook Question
Chapter 9, Problem 11PP
PRACTICE PROBLEM 9.11
Draw the most stable chair conformation of 1-bromo-2-chlorocyclohexane, if the coupling constant between hydrogens on C1 and C2 was found to be 7.8 Hz
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Students have asked these similar questions
Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide.
(a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds.
(b) Then analyze the stereochemistry of the product.
racemic
chiral
achiral
(1R, 3S)
(1R, 3R)
(1S, 3S)
(a)
(d)
5. Assign the R and S configurations for all stereogenic centers in the following compounds.
BI
H
CH(CH₂)₂
KAMION
WOH
H₂C H
CH₂
Br -H
Br
+H
CH,
(0)
CH=CH₂
H+C₂0
-C=CCH₂
CH₂CH₂CH₂C1
CH₂CH₂CI
H₂NH
CH₂CH₂Cl
CH₂CH₂CH₂OH
H₂N CH₂CH₂OH
CH₂
E
In the equilibrium reaction of the conformations of 1,3-butadiene, what adequately explains the 15
kJ/mol energy barrier between the s-cis and s-trans conformation?
15 kJ/mol
Sterics cause the s-cis conformation to be more stable
and, therefore, higher in energy.
(B) The л-bonds are not conjugated during the conversion
of one conformation to the other.
The s-trans is more stable because it is aromatic.
The s-cis is less stable because it is non-aromatic.
(E) Both the s-cis and s-trans are conjugated because all
carbons are sp³-hybridized.
0°
90°
Dihedral angle
180°
Chapter 9 Solutions
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
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- (b) Consider the following tetra-substituted cyclohexane: OH Draw the alternative chair conformations of the cyclohexane compound, shown above. List the unfavourable steric interactions for each chair conformation and determine the more stable conformation of the compound. i.arrow_forward(5) Draw the most stable chair conformation of the cyclohexane shown below. CH3 CI H3C Br OH CH3arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward
- Please draw the most stable chair conformation for: (a) bromocyclohexane (b) trans-1-ethyl-3-methylcyclohexanearrow_forward1) What is the lowest energy conformation of each molecule below? Justify your answer. For the first molecule, show a reaction coordinate diagram for the interconversion between the two trans-isomers. OCH3 OCH3 Farrow_forward5.76 2,3-Dibromoprop-1-ene (C3H4Br₂) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule with the formula C3H3Br₂Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br₂Cl; (b) enantiomers of C3H3Br₂Cl; (c) diastereomers of C3H3Br₂Cl. co 11 HHH Juods H Brugtrio 2 bas A 2,3-Dil so ontemme A chon Br 2,3-Dibromoprop-1-enearrow_forward
- 1) What is the lowest energy conformation of each molecule below! Justify your answer. For the first molecule, show a reaction coordinate diagram for the interconversion between the two trans-isomers. OCH3 $ OCH3arrow_forwardDraw all the possible conformations for the compounds below. Identify the most stable conformation for each of the following compounds. Give reason(s) for your answer. (i) 1-hydroxy-2,3-dichlorocyclohexane (ii) 1-ethyl-2-methylcyclohexanearrow_forward(a) How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.arrow_forward
- 2.(a) Different conformations are found in 2-methylpentane. (i) Using Newman Projection, draw all the possible staggered and eclipsed conformations of pentane by referring to the bond rotation at C3-C4.(ii) Compare their stability and explain your answer.arrow_forwardWhat is the degree of unsaturation for compoundC11H7ClO?arrow_forward1. Following are stereorepresentations for the four stereoisomers of 3-chloro-2-butanol. CH3 CH3 CH3 CH3 H HÔ► H HO► H НО CI H. CI Hi Cl Cl CH3 CH3 CH3 CH3 (1) (2) (3) (4) (a) Assign an R or S configuration of each chiral center. Name each (b) Which compounds are enantiomers? (c) Which compounds are diastereomers? (d) Which are meso compounds?arrow_forward
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