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EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 15, Problem 15.3P
Interpretation Introduction
Interpretation:
Concept introduction:
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In
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Draw the s-cis and s-trans conformers of (Z,Z)-2,7-dimethylocta-3,5-diene. Which conformer is least stable?
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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)
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?
Chapter 15 Solutions
EBK 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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Diels–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_forwardThere is a diene of molecular formula C5H8 that is chiral. Draw its structure.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 often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forward
- The 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_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_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_forward
- Diels–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 often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_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_forward5 (a) (8 pts) (a) Box the most stable Z alkene (make sure it's Z!). (b) Circle the least stable E alkene. (c) Label two alkenes which are neither E or Z. NH₂ 5 Je č F HO NH₂ SH 5(b) (4 pts) Draw an example of two conformations of a molecule of your choice, and then draw a separate example of two stereoisomers of another molecule of your choice.arrow_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_forwardTRUE OR FALSE i. A =C-Br bond is more polar than a -C-Br bond. ii. A bromonium ion can undergo hydride or methyl shift to produce a more stable carbocation. iii. The two conformers of cis-1,3-diaminocyclohexane will have equal stability.arrow_forward2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.arrow_forward
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