Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 3.14, Problem 49P
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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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-
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
8. 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
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Chapter 3 Solutions
Organic Chemistry
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. 11PCh. 3.2 - Prob. 12PCh. 3.3 - Prob. 13PCh. 3.3 - Prob. 14P
Ch. 3.3 - Prob. 15PCh. 3.3 - Prob. 16PCh. 3.3 - What is each compounds systematic name?Ch. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 19PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Prob. 23PCh. 3.6 - Prob. 24PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Prob. 26PCh. 3.7 - Prob. 27PCh. 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. 30PCh. 3.9 - Prob. 31PCh. 3.9 - Prob. 32PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.9 - Prob. 35PCh. 3.9 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - a. Draw all the staggered and eclipsed conformers...Ch. 3.10 - Prob. 38PCh. 3.10 - Using Newman projections, draw the most stable...Ch. 3.11 - The bond angles in a regular polygon with n sides...Ch. 3.11 - Prob. 41PCh. 3.11 - Prob. 42PCh. 3.12 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.13 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.13 - Using the data in Table 3.9, calculate the...Ch. 3.14 - Prob. 46PCh. 3.14 - Which has a higher percentage of the...Ch. 3.14 - For each of the following disubstituted...Ch. 3.14 - 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. 53PCh. 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. 63PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 66PCh. 3 - Prob. 67PCh. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 69PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Prob. 71PCh. 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 - Prob. 80PCh. 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. 85PCh. 3 - Using the data obtained in Problem 85, calculate...
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- 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) Varrow_forwardWhich 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_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
- The 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_forward3. 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_forward
- Draw alternative chair conformations for the following substituted cyclohexane and determine which chair is more stable. C HO H ОН In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: Group b: Group c:arrow_forwardH;C-CH2-CH–CH3 CH₂-CH3 Relative to the molecule above, which of the below is not a conformer? A. C. HỌC-CH,-CH–CH, CH H₂-CH-C CH3 CH3 CH3-CH-CH-CH3 13-CH-C CH3 B. D. CH3 CH3 CH₂-CH-CH₂ CH3 CH₂ CH-CH₂-CH3 CH₂ CH3arrow_forwardDraw the two chair conformers for each of the following and indicate which conformer is more stable:a. cis-1-ethyl-3-methylcyclohexane d. cis-1,2-diethylcyclohexaneb. trans-1-ethyl-2-methylcyclohexane e. cis-1-ethyl-3-isopropylcyclohexanec. trans-1-ethyl-2-isopropylcyclohexane f. cis-1-ethyl-4-isopropylcyclohexanearrow_forward
- 4. 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_forward5. 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_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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