Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 4.SE, Problem 23VC
Name the following compound, identify each substituent as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (green=Cl):
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Starting from the Newman projection below, rotate the back
carbon to provide the structure in the least stable
conformation.
(H3C)₂HC H
Q
IX
H^
H
H
CH3
o
NH2
Br
1 OH
ОН
(a) Use the template below and drawa Newman projection for this conformation of the compound when viewed along the C2-C3
bond.
CH2OH
(b) Why is this the most stable conformation?
Following is the Structural formal of Chloropropane
H H H
2.
H
Draw Newman projections for all staggered and eclipsed conformation formed by
rotation about C1 - C2 bond from 0° to 360°.
b) Which Staggered conformation(s) has the lowest energy; which has the highest
energy?
c) Which eclipsed conformation(s) has the lowest energy, which has thhe highest
energy?
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
Knowledge Booster
Learn more about
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
- Draw the most stable conformation of 1,4-dichlorobutane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper, respectively.arrow_forwardPrautice qt#12 For the following compound, draw the appropriate Newman projection along the C1-C2 bond of the following: HE Су a) The most stable conformer and name the conformer. b) The least stable conformer and name the conformer. c) The second most stable conformer and name the conformer.arrow_forwardWhich of the following line drawings represents the correct stereochemistry o molecule shown in the Newman projection below? E + Н. H I CH₂CH3 LOH H CH3 OH OH || IV OH 5.... OH A) I B) II C) III D) IV Karrow_forward
- Starting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the most stable conformation. H₂C H (H3C) 3C H H CH3 →arrow_forwardAre the C¬C bonds cyclopropane weaker than those in cyclohexane?arrow_forwardBuild a model (attach a photo) of the following Newman projection viewed along the C2→C3 bond. Draw a line structure of the most stable conformation with the -CH2OH on the left hand side: 1.2 H HO Br- 'Bu CH,OH 1arrow_forward
- Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable. H,C CH3 H H H CH3arrow_forwardCalculate the number of degrees of unsaturation for each molecular formula, and propose two possible structures: (a) C8H12; (b) C10H10.arrow_forward5) For the following: a) Draw the "flat" line structure of the following (be sure to indicate stereochemistry) Br OH b) Draw both chair conformations of the following compound. Indicate which form is the most stable H3C°arrow_forward
- CH, CH, CH CH, H CH H H B C CH, CH, H H CH, D a) Give the names of conformers, in the order shown. (2) b) Rank the four conformers in order of stability starting with the LEAST stable, through the MOST stable. (2) c) State the value of the dihedral angle for each conformer. (2)arrow_forward3 Flourinated hydrocarbons such as CHF2-CHF2 are used in refrigerants (A) Draw in a NEWMAN projection two conformational stereoisomers of CHF2-CHF2 that are conformational enantiomers of each other. Identify if this is an OclipOd or staggered conformation. There are multiple correct answers to this. (B) Draw in a NEWMAN project the conformer of CHF2-CHF2 that has a mirror image that is superimposable on itself. There is more than one correct answer to this.arrow_forwardDraw the structure for the most stable chair conformation of trans-1-tert-butyl-3-chlorocyclohexane. Use the cyclohexane conformation drawing tool and guide points to draw each structure. C1 M C™ X Ĉarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License