Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 3, Problem 54P
For rotation about the C-3 8 C-4 bond of 2-methylhexane, do the following:
- a. Draw the Newman projection of the most stable conformer.
- b. Draw the Newman projection of the least stable conformer.
- c. About which other carbon–carbon bonds may rotation occur?
- d. How many of the carbon–carbon bonds in the compound have staggered conformers that are all equally stable?
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For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents.
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?
Draw the following conformers of hexane, considering rotation about the C3–C4 bond:
a. The most stable of all the conformers
b. The least stable of all the conformers
c. The gauche conformer
For rotation about the C-3 - C-4 bond of 2-methylhexane, do the following: a. Draw the Newman projection of the most stable conformer. b. Draw the Newman projection of the least stable conformer. c. About which other carbon–carbon bonds may rotation occur? d. How many of the carbon–carbon bonds in the compound have staggered conformers that are all equally stable?
Chapter 3 Solutions
Essential Organic Chemistry, Global 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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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
- 1. Draw the two conformations of trans-1-bromo-3-methylcyclohexane using both the Newman projection and the chair drawing. Calculate the energies of each. What ratio of the two conformers will be present at equilibrium? 2. Draw a structure of a chiral alcohol.arrow_forwardFor each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for substituents. 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? [1] [2] [3]arrow_forwardWhich of the following represents the more stable chair conformer of the compound below? Question 1 Answer a. b. C. H₂C d. CH₂ Bo H₂C CH3 хоarrow_forward
- 9. Using Newman projections, draw the most stable conformer for the following: 3-methylpentane, considering rotation about the C-2-C-3 bond b. 3-methylhexane, considering rotation about the C-3-C-4 bond 3,3-dimethylhexane, considering rotation about the C-3-C-4 bond lavalahavane, a. C.arrow_forwardChoose the statement that is incorrect about rings. اختر احدى الاجابات А. Planar cyclobutane is its most stable conformation. В. Planar cyclopentane would have small angle strain but severe torsional strain. C. The chair conformation of cyclohexane has no angle or torsional strain. D. Cyclopropane has the greatest angle strain. Е. The chair conformation has less torsional strain and fewer nonbonded interactions than the twist boat conformation.arrow_forwardFor 1,2-dichloroethane: a.Draw Newman projections for all eclipsed conformations formed by rotation from 0° to 360° about the carbon-carbon single bond. b.Which eclipsed conformation(s) has (have) the lowest energy? Which has (have) the highest energy? c.Which, if any, of these eclipsed conformations are related by reflection?arrow_forward
- 2. Draw the Newman projection for the following compound by looking down the C2–C3 bond. Rotate about the C2–C3 bond and draw two additional staggered conformations. Predict which one is the most stable conformer.arrow_forwardUsing the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. A. From the nine stereoisomers, identify one pair of enantiomers. B. Draw the most stable conformer of the most stable stereoisomer.arrow_forwarda. Using the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. b. From the nine stereoisomers, identify one pair of enantiomers. c. Draw the most stable conformer of the most stable stereoisomer.arrow_forward
- 4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forward• Draw the chair conformations of the following compounds and determine which geometric isomer is more stable. Also show using Newman projection that one conformation is more stable than the other. a. cis-1-isopropyl-2-methylcyclohexane b. 1-methycyclohexanearrow_forwardConsider pentane, C5H12. Looking through the internal C3-C4single bond, draw thesix Newman projections (where the angle between two bonds as you look through the C3and C4bond is either 0°or 60°of the different conformations. Label the conformers/rotamers using I, II, etc. a.Which conformer is the most stable? the least stable? b.Which rotamer is the anticonformer? the gaucheconformer? c.Draw the anticonformer in saw horse projection.arrow_forward
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