Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 3.15, Problem 51P
For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:
- a. cis-1,2-
- b. trans-1,2-
- c. cis-1,3-
- d. trans-1,3-
- e. cis-1,4-
- f. trans-1,4-
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1,3-dimethylcyclohexane can exist in a chair conformation with its substituents in the equatorial and axial positions. Which is the most preferred conformation of the compound?
a. Trans-1,3-dimethylcyclohexane
b. None of the choices
c. Cis-(e)-1,3-dimethylcyclohexane
d. Cis-(a)-1,3-dimethylcyclohexane
F
H
CH3
H CH₂CH3-
H
CH₂CH3
Several conformations of a molecule are depicted as Newman projections. Which
of the conformations is the most stable?
IV
CH₂CH3
H3C
H
H
H
.F
H
CH3
H
III
CH₂CH3
FH
H3C
CH₂CH3
H
-H
H
-H
CH3
A) I
B) II
C) III
D) IV
E) V
Draw two chair conformations of cis-1-bromo-4-isopropylcyclohexane. Which one is the most stable?
a. a,e-Cis
b. e,a-Cis
c. a,a-Cis
d. e,e-Cis
Chapter 3 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structure of a compound with molecular...Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Prob. 6PCh. 3.1 - Draw the structure for each of the following: a....Ch. 3.1 - Name the following compounds: a. CH3OCH2CH3 b....Ch. 3.2 - Prob. 9PCh. 3.2 - Draw the structure for each of the following: a....Ch. 3.2 - Give each substituent on the nine-carbon chain a...Ch. 3.2 - Prob. 14P
Ch. 3.3 - What is each compounds systematic name?Ch. 3.3 - Prob. 16PCh. 3.3 - Prob. 17PCh. 3.3 - Prob. 18PCh. 3.3 - Prob. 19PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 21PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Prob. 25PCh. 3.6 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Draw condensed and skeletal structures for each of...Ch. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 32PCh. 3.9 - Prob. 33PCh. 3.9 - Prob. 34PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.10 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - Prob. 38PCh. 3.10 - Prob. 39PCh. 3.11 - a. Draw all the staggered and eclipsed conformers...Ch. 3.11 - Prob. 41PCh. 3.11 - Using Newman projections, draw the most stable...Ch. 3.12 - The bond angles in a regular polygon with n sides...Ch. 3.12 - Prob. 44PCh. 3.13 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.14 - Using the data in Table 3.9, calculate the...Ch. 3.14 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.15 - Prob. 48PCh. 3.15 - Which has a higher percentage of the...Ch. 3.15 - a. Draw the more stable chair conformer of...Ch. 3.15 - For each of the following disubstituted...Ch. 3.15 - a. Draw Newman projections of the two conformers...Ch. 3.15 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 56PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 66PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 69PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 72PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - What is each compound s systematic name?Ch. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 88PCh. 3 - Using the data obtained in Problem 85, calculate...Ch. 3 - Draw the conformers for the following...
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- Which of the following conformations of 1,2-dibromocyclohexane is the LEAST stable? Select one: Br a. Br Br -H Ob. Br H Br Br c. Br Br d. Harrow_forward8. Which of the following is the most stable conformation of trans-1-tert-butyl-3- methylcyclohexane? C(CH3)3 C(CH3)3 CH3 CH3 CH3 C(CH3)3 H3C A Вarrow_forwardWhich among the conformers below is the most stable conformation for cis-1-bromo-3 methylcyclohexane? Br (A) O a. Conformer D O b. Conformer A Oc. Conformer C O d. Conformer B Br Br (B) (C) (D)arrow_forward
- 3. For the following conformation of 1,3-dimethylcyclohexane: H₂C. -CH3 A a) Is this a chair conformation of cis- or trans- isomer of 1,3-dimethylcyclohexane? b) Draw the alternative chair conformation of this compound. Which chair conformation is more stable? c) Draw a planar hexagon representation of the isomer A. d) Draw a Newman projection of isomer A.arrow_forwardThe most stable conformation of 1,2-dibromoethane is: Select one: Br H. Br Br H. H. Br Br H. Br Br Br Br H.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
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- 5. Given the molecule 1,2-dimethyl-4-bromocyclohexane below: CH3 20 Br "CH 3 NOTE: All groups are cis with respect to each other. a. Draw the chair and the flipped chair conformation of the molecule above. Label the chair conformation with "A" and the flipped chair conformation with "B". b. Which of the two: chair or flipped chair is more stable, justify your answer.arrow_forward4. Draw the Newman projection of the conformer below as it is drawn looking down the indicated C-C bond. Then draw the most stable conformer and the least stable conformer as Newman projections. PH. CH3 H H CI Newman of Drawn Newman of Most Newman of Least Conformer Stable Conformer Stable Conformerarrow_forwardMatch Br CH3 CH3 CH3 CH Br Br CH3 CH3 H. H H. вн 1. least stable conformer [ Select ] 2. the numerical value for the overall AG° for conformer B going to C ISelect ] 3. the numerical value for the Keg conformer B going to C [ Select ]arrow_forward
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