Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 71P
- a. Draw a potential energy diagram for rotation about the Ci C bond of 1,2-dichloroethane through 360, starting with the least stable conformer. The anti conformer is 1.2 kcal/mol more stable than a gauche conformer. A gauche conformer has two energy barriers, 5.2 kcal/mol and 9.3 kcal/mole.
- b. Draw the conformer that would be present in greatest concentration.
- c. How much more stable is the most stable staggered conformer than the most stable eclipsed conformer?
- d. How much more stable is the most stable staggered conformer than the least stable eclipsed conformer?
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Students have asked these similar questions
Glucose is a simple sugar with five substituents bonded to a sixmembered ring.a.Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.
b.Convert this representation to one that uses a hexagon with wedges and dashed wedges.
c.Draw a constitutional isomer of glucose.
d.Draw a stereoisomer that has an axial OH group on one carbon.
Question 2 please
8. Which of the following is the most stable staggered conformer?
Me
H
OH
Me
Me
OH
Me
OH
Me
H
Conformer A
OH
HO
H
Conformer B
OH
H
H
Me
Conformer C
a. Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing
effect.
b. Conformer A because there are only two gauche interactions, and hydrogen bonding
between the two OH groups is a stabilizing effect.
c. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen
bonding between the two OH groups is a stabilizing effect.
d. Conformer B because the large OH groups are anti to each other.
Chapter 3 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Draw the structure for each of the following...Ch. 3.1 - Name the following compounds:Ch. 3.1 - Prob. 7PCh. 3.2 - What is each compounds systematic name?Ch. 3.2 - Prob. 11PCh. 3.3 - Prob. 12PCh. 3.3 - Convert the following condensed structures into...Ch. 3.3 - The molecular formula for ethyl alcohol (CH3CH2OH)...
Ch. 3.3 - Draw a condensed and a skeletal structure for the...Ch. 3.3 - What is each compounds systematic name?Ch. 3.4 - Prob. 17PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.5 - Are the following compounds primary, secondary, or...Ch. 3.5 - Name the following amines and tell whether they...Ch. 3.5 - Draw the structures and provide systematic names...Ch. 3.6 - Predict the approximate size of the following bond...Ch. 3.7 - What is the smallest straight-chain alkane that is...Ch. 3.7 - Prob. 24PCh. 3.7 - Prob. 25PCh. 3.7 - Prob. 26PCh. 3.7 - List the compounds in each set from highest...Ch. 3.8 - Rank the following compounds in each set from most...Ch. 3.8 - In which solvent would cyclohexane have the lowest...Ch. 3.8 - Prob. 30PCh. 3.9 - Prob. 31PCh. 3.9 - a. Draw the three staggered conformations and the...Ch. 3.9 - a. Draw the most stable conformation of pentane...Ch. 3.11 - Draw 1,2,3,4,5,6-hexachlorocyclohexane with a. all...Ch. 3.12 - At any one time, would you expect there to be more...Ch. 3.13 - Prob. 36PCh. 3 - a. How many hydrogens does an alkane with 17...Ch. 3 - Prob. 2PCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 39PCh. 3 - Prob. 40PCh. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Name the following amines and tell whether they...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - What is each compounds name? a. CH3CH2CH2OCH2CH3Ch. 3 - Draw the structural formula for an alkane that has...Ch. 3 - Which has a. the higher boiling point:...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 51PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - Prob. 53PCh. 3 - For rotation about the C-3 8 C-4 bond of...Ch. 3 - Prob. 55PCh. 3 - What is each compounds systematic name?Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Draw the nine constitutional isomers with...Ch. 3 - Prob. 59PCh. 3 - Prob. 60PCh. 3 - Prob. 61PCh. 3 - Using Newman projections, draw the most stable...Ch. 3 - For each of the following disubstituted...Ch. 3 - Prob. 64PCh. 3 - Prob. 65PCh. 3 - What is each compounds systematic name?Ch. 3 - Prob. 67PCh. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Prob. 69PCh. 3 - Prob. 70PCh. 3 - a. Draw a potential energy diagram for rotation...
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- Consider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?arrow_forwardNeuroprotectin D1 (NPD1) is synthesized in the body from highly unsaturated essential fatty acids. NPD1 is a potent natural anti-inflammatory agent.a.Label each carbon–carbon double bond as conjugated or isolated. b.Label each double bond as E or Z. c.For each conjugated system, label the given conformation as s-cis or s-trans.arrow_forward6. Consider the structure of cis-1,2-dimethylcyclopropane and trans-1,2-dimethylcyclopropane A. Which compound is more stable? Explain. B. Which compound will release more heat upon combustion? Explain C. Based on the following interactions, predict the difference in energy between the cis and trans isomers. Each CH3 Each CH3 Each H Each H CH3 gauche interaction is worth 0.9 kcal/mol CH3 eclipsed interaction is worth 2.6 kcal/mol CH3 eclipsed interaction is worth 1.4 kcal/mol H eclipsed interaction is worth 1.0 kcal/molarrow_forward
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