Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 15, Problem 15.3P
Interpretation Introduction
Interpretation:
Concept introduction:
In
In
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Draw the compunds below.
(2e,4z)-1-bromo-4-methylhexa-2,4-diene
(2e,4z)-5-bromo-3-methylhexa-2,4-diene
(2z,4e)-1-bromo-4-methylhexa-2,4-diene
(2z,4e)-1-bromo-3-methylhexa-2,4-diene
What are the relative energy levels of the three staggered conformations of 2,3-dimethylbutane when looking down
the C2-C3 bond?
Me
Me
H
Me
Me Me
Me Me.
Me
Conformation:
191 1ක් පුදා
H
Me
Me
Me
H
H
H
A
B
C
Me
A is the highest energy conformation and C is the lowest (energy level of B is in between the two)
O A and B are equal energy, and C is the highest energy conformation
A and B are equal energy, and C is the lowest energy conformation
C is the highest energy conformation and A is the lowest (energy level of B is in between the two)
O B is the highest energy conformation and C is the lowest (energy level of A is in between the two)
Draw (1R,3S)-1,3-dimethylcyclohexane, in its minimum energy conformation. Then draw the Newman Projection for this structure with the correct stereochemistry and in its minimum energy state.
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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- Following is a staggered conformation for one of the enantiomers of 2-bromobutane, and several purported Newman projections for this conformation. H H H3C Br H CH3 2-bromobutane H H (a) Is this (R)-2-bromobutane or (S)-2-bromobutane? CH3 CH3 Br H H H CH3 Br b CH3 H Br H CH3 CH3 H (b) Which of the following Newman projections is equivalent to the wedge-dash structure when viewed along the horizontal axis?arrow_forwardWhen HBr adds across the double bond of 1,2-dimethylcyclopentene, the product is a mixture of the cis and trans isomers. Show why this addition is not stereospecific.arrow_forwardDiels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.arrow_forward
- Draw the structure of (1S,3S)-1-isopropyl-3-methylcyclopentane 2-methylpentane (S)-4-ethyloctane cis-1,3-dichlorocyclohexane (2S,3R)-2,3-dibromopentane (R)-2-chloro-5,5-dimethylheptane. Please answer fast I give you upvote.arrow_forwardIn 4+2 cycloaddition, ENDO stereochemistry is preferred because: endo stereochemistry allows the diene to adopt s-cis conformation. endo stereochemistry results in less steric hindrance. the transition state leading to endo stereochemistry is higher energy. it allows for additional π to π overlap between the diene and the dienophile.arrow_forwardDraw the structure of each compound.a. (Z)-penta-1,3-diene in the s-trans conformationb. (2E,4Z)-1-bromo-3-methylhexa-2,4-dienec. (2E,4E,6E)-octa-2,4,6-triened. (2E,4E)-3-methylhexa-2,4-diene in the s-cis conformationarrow_forward
- D. Rank (increasing) the substituents in each of the following sets: (а) -Н, -ОН, -ОСH3, -СH, (Б) -Вr, -СНз, -СНBr, -а (c) -CH=CH2, -CH(CH3)2, -C(CH3)3, -CH 2CH3arrow_forwardWhich compounds have torsional strain (also known as eclipsing strain) in their most stable conformation? Note that compound that has two rings has been drawn in its most stable conformation. Select more than one answer. Even the correct answer gets feedback on this one. Me Me Me Me Me Me D E A. Cyclohexane is a chair, which has only secondary carbons. Since cyclopropane is flat all of the adjacent C's are eclipsed, this giving rise to torsional strain. Since cyclopropane is flat all of the adjacent C's are eclipsed, this giving rise to torsional strain. DEarrow_forwardOne of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, called myo-Inositol, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-Inositol (Note: account the wedge and dash projection). Draw the most stable cis-trans stereoisomer of myo-Inositol. OH HO ОН HO "OH ОНarrow_forward
- I need an explanation on this problem.arrow_forwardThe alkyl halide shown below in line-bond structure is the product of ethene hydrohalogenation. Choose the model(s) that correspond to this conformation. с D A B H H H H A O -Harrow_forward(5) Draw the most stable chair conformation of the cyclohexane shown below. CH3 CI H3C Br OH CH3arrow_forward
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