Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 4, Problem 17PP
Practice Problem 4.17
Write a conformational structure for 1-bromo-3-chloro-5-fluorocyclohexane in which all the substituents are equatorial. Then write its structure after a ring flip.
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Consider 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?
5.76 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.
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2,3-Dibromoprop-1-ene
Consider 1-bromopropane, CH3CH2CH2Br.
(a) Which of these is the lowest energy conformation?
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
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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
- (a) which if the structure of trans-1,2-dimethylcyclopentane? (b) which is the most stable conformation of 1-bromo-2-ethylcyclohexane? (c) which is the least stable conformation of 1-bromo-2-ethylcyclohexane? (d) which is the more stable configuration of 1,3-dimethylcyclopentane? *Et = ethylarrow_forward2.34 Consider 1-bromopropane, CH3CH2CH2Br.(a) Draw a Newman projection for the conformation in which !CH3 and !Br are anti (dihedral angle 1808).(b) Draw Newman projections for the conformations in which !CH3 and !Br are gauche (dihedral angles 608 and 3008).(c) Which of these is the lowest energy conformation?(d) Which of these conformations, if any, are related by reflection?arrow_forward3B. For each compound below, draw two chair conformations. Indicate whether the substituents are axial or equatorial. Indicate which chair conformation is more stable. (you need to draw conformations of the exact molecule, not its mirror image or diastereomer) (a) (b) (c) Ме Me Et "Et Et Mearrow_forward
- Draw 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) All Isomers have the same molecular formulae. Explain this further. Hint what does it mean to have the same molecular formulae? (b) What is Constitutional (structural) isomerism? Hint, isomers are different, so what is different between a pair of constitutional isomers (see the chart on the last page for examples). (c) What is Conformational isomerism?arrow_forwardWrite a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.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_forward3. (20) Cyclohexane may go through ring-flipping as shown below. 5 (a) Draw both of the possible chair conformations for cis-1-tert-butyl-4-methylcyclohexane by copying the scheme above followed by adding appropriate substituents to axial or equatorial positions. (b) Circle the more stable conforms of (A) and (B)arrow_forward4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4- Dibromocyclohexane. 4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-Dibromocyclohexane. 4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4- Dibromolcyclohexane. Explain the reason for your choice.arrow_forward
- Refer the structure below: CH3 CH3 CH3 CH3 Compound I Compound II (i) Are the above cyclohexane derivatives cis- or trans-isomer? (ii) Redraw the structure in chair conformation and identity which of these the most and the least stable.arrow_forwardDraw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3- dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a ) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?arrow_forwardRefer to the structures below to answer the following questions: Compound A Compound B (i) Are the cyclohexane derivatives shown above cis- or trans-isomer? (ii) Redraw the structure in chair conformation, and identify which of these structures is the most and the least stable.arrow_forward
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