Get Ready for Organic Chemistry
2nd Edition
ISBN: 9780321774125
Author: KARTY, Joel
Publisher: PEARSON
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Question
Chapter 4, Problem 4.13YT
Interpretation Introduction
Interpretation:
The
Concept introduction:
The eclipsed conformation possesses the most torsional strain.
Expert Solution & Answer
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3. Draw both chair conformations for the cyclohexane molecule shown below, and circle the
most stable conformation (the methyl group is larger than the hydroxyl group).
OH
H3C
न
A
8-£
B
a) Draw all Newman projections
of your molecule's conformations
in which the CH3 group and the
H of the CHY2 group are
positioned 'ANTI' to each other.
Be sure to put in the correct X
and Y atoms, bonded to the
correct C atoms, for your
molecule. X = FY=I
Conformations = 60 deg and
-
180 deg 60 deg dihedral angle
= - 179.987 deg 180 deg ·
-
dihedral angle
=
179.814 deg
Chapter 4 Solutions
Get Ready for Organic Chemistry
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - Prob. 4.3PCh. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Prob. 4.8PCh. 4 - Prob. 4.9PCh. 4 - Prob. 4.10P
Ch. 4 - Prob. 4.11PCh. 4 - Prob. 4.12PCh. 4 - Prob. 4.13PCh. 4 - Prob. 4.14PCh. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Prob. 4.17PCh. 4 - Prob. 4.18PCh. 4 - Prob. 4.19PCh. 4 - Prob. 4.20PCh. 4 - Prob. 4.21PCh. 4 - Prob. 4.22PCh. 4 - Prob. 4.23PCh. 4 - Prob. 4.24PCh. 4 - Prob. 4.25PCh. 4 - Prob. 4.26PCh. 4 - Prob. 4.27PCh. 4 - Prob. 4.28PCh. 4 - Prob. 4.29PCh. 4 - Prob. 4.30PCh. 4 - Prob. 4.31PCh. 4 - Prob. 4.32PCh. 4 - Prob. 4.33PCh. 4 - Prob. 4.34PCh. 4 - Prob. 4.35PCh. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Prob. 4.39PCh. 4 - Prob. 4.40PCh. 4 - Prob. 4.41PCh. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - Prob. 4.47PCh. 4 - Prob. 4.48PCh. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - Prob. 4.51PCh. 4 - Prob. 4.52PCh. 4 - Prob. 4.53PCh. 4 - Prob. 4.54PCh. 4 - Prob. 4.55PCh. 4 - Prob. 4.56PCh. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Prob. 4.61PCh. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - Prob. 4.64PCh. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Prob. 4.68PCh. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Prob. 4.73PCh. 4 - Prob. 4.1YTCh. 4 - Prob. 4.2YTCh. 4 - Prob. 4.3YTCh. 4 - Prob. 4.4YTCh. 4 - Prob. 4.5YTCh. 4 - Prob. 4.6YTCh. 4 - Prob. 4.7YTCh. 4 - Prob. 4.8YTCh. 4 - Prob. 4.9YTCh. 4 - Prob. 4.10YTCh. 4 - Prob. 4.11YTCh. 4 - Prob. 4.12YTCh. 4 - Prob. 4.13YTCh. 4 - Prob. 4.14YTCh. 4 - Prob. 4.15YTCh. 4 - Prob. 4.16YTCh. 4 - Prob. 4.17YTCh. 4 - Prob. 4.18YTCh. 4 - Prob. 4.19YTCh. 4 - Prob. 4.20YTCh. 4 - Prob. 4.21YTCh. 4 - Prob. 4.22YTCh. 4 - Prob. 4.23YTCh. 4 - Prob. 4.24YTCh. 4 - Prob. 4.25YT
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- From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their substituents in an axial orientation for the following compounds: (a) Isopropylcyclohexane (b) Fluorocyclohexane (c) Cyclohexanecarbonitrile, C6H11CNarrow_forwardLook at Figure 4-12 on page 105, and estimate the percentages of axial and equatorial conformations present at equilibrium in bromocyclohexane.arrow_forwardCalculate strain energy for the conformer pictured below, using strain energy increments from the table. Strain Energy for Alkanes Interaction / Compound kJ/mol H: H eclipsing 4.0 H: CH3 eclipsing CH3 CH3 eclipsing gauche butane H Strain energy = cyclopropane cyclobutane cyclopentane cycloheptane cyclooctane (Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case sensitive.) H CH3 ball & stick V + labels 5.8 11.0 3.8 115 H kcal/mol 110 26.0 26.2 40.5 1.0 1.4 2.6 0.9 27.5 26.3 6.2 6.3 9.7arrow_forward
- Using solid and dashed wedges, draw the structure of (1S, 2S, 4R, 5R)-1,5-dibromo-2,4- dichlorocyclohexane, then draw the most stable conformer.arrow_forwarda. For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. ( see image) b.Draw and name the seven constitutional isomers (all contain a ring of some size) for cycloalkane, C6H12.arrow_forwardSight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forward
- 4. a) Calculate the units of unsaturation for the formula C6H10O2. b) Draw a structure of C6H1002 that has no formal charges and a) ester and ring b) carboxylic acid lotfasss.com 5. A student tried to draw the most stable conformation of the molecule shown below. What is wrong with the Newman projection that they drew? view OCH 3 H H H 6. A student tried to draw one of the chair conformations of the molecule shown below. What is wrong with the chair that they drew? H3C Student answer for most stable Newman Projection H3C. CH3 H OH TH H H H UU .H OCH 3 has: c) ketone and alcohol H 7. Which type(s) of strain are present in the following molecules? (steric, torsional, angle, etc) H H O H H H H H Harrow_forwardA Newman projection of methylcyclohexane is shown below. List the types of strain present in this conformation. H. H. H. H2 CH3 C H2 H.arrow_forward5. Construct a model of cyclohexane (C6H12) and draw it below.arrow_forward
- By considering viewed through the C-2-C-3 bond, which below conformations of 2,3- dibromobutane show the most stable and the least stable conformation? Clearly explain the reason, why? S CH3 H H Br. H3C, Br H3C Br Br Br H. Br CH3 ČH3 H I II III Br Br H3C, Br H3C H. H3C" H. Br ČH3 IV Varrow_forward16. Choose the correct New- man projection that cor- responds to point A on the graph of chemical potential energy vs. tation about the C2-C3 ro- bond of butane. A) H H CH3 H CH3 B) H 个 Potential Energy H H CH3 d CH3 H H 0 A 60 C) HH 120 180 240 300 Degrees rotation →→→→ H CH3 CH3 H 360 H3C CH3 пон D) H A H Harrow_forward8. Write the most stable conformer of the following molecules A and B. Calculate the gauche interactions in each and find the difference in their energy. H H H A H H ď H B H Harrow_forward
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