Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 74P
Draw the two chair conformers for each of the following and indicate which conformer is more stable:
- a. cis-1-ethyl-3-methylcyclohexane
- b. trans-1-ethyl-2·methylcyclohexane
- c. trans-1-ethyl-2-isopropylcyclohexane
- d. cis-1,2·diethylcyclohexane
- e. cis-1-ethyl-3-isopropylcyclohexane
- f. cis-1-ethyl-4-isopropylcyclohexane
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Chapter 3 Solutions
Organic Chemistry (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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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
- Given the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C. H A CH3 How is Compound A related to the chair conformation? It is a stereoisomer. It is a conformation isomer (conformer). H3C- It is a constitutional isomer. It is not an isomer.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_forwardDraw the two chair conformers for each of the stereoisomers of trans-1-tert-butyl-3-methylcyclohexane. a. For each pair, indicate which conformer is more stable.arrow_forward
- Draw the more stable chair conformation for each compound. a. trans-1-isopropyl-3-methylcyclohexane b.cis-1-sec-butyl-4-ethylcyclohexane c. cis-1-ethyl-2-isobutylcyclohexane d. trans-1,2-dibutylcyclohexanearrow_forwardThere are the two possible chair conformations of trans-1-Methyl-4-chlorocyclohexane. What is the energy difference between the two chair conformations? Table 1. Steric Strain in Monosubstituted Cyclohexanes a 28 b. 56 c. 4.8 d 9.6arrow_forwardGiven the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C. A CH3 How is Compound A related to the chair conformation? H. O It is a stereoisomer. H3C- O It is a constitutional isomer. O It is a conformation isomer (conformer). H O It is not an isomer. B How is Compound B related to the chair conformation? H3C H3C- O It is a conformation isomer (conformer). O It is a stereoisomer. O It is a constitutional isomer. O It is not an isomer. CH3 How is Compound C related to the chair conformation? H3C. O It is a conformation isomer (conformer). H O It is not an isomer. ČH3 O It is a constitutional isomer. O It is a stereoisomer D How is Compound D related to the chair conformation? H3C. -CH3 O It is a stereoisomer. O It is not an isomer. H. O It is a conformation isomer (conformer). O It is a constitutional isomer.arrow_forward
- Given the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C, B H. How is Compound B related to the chair conformation? O It is a conformation isomer (conformer). H3C H3C H O It is a constitutional isomer. O It is not an isomer. H. O It is a stereoisomer.arrow_forwardWhich statement is true about these conformers? H. H. H H CH3 H3C H. H,C H,C H. H. A O A and B are equally stable O Difficult to predict O A more stable than B ) B more stable thanarrow_forwardAnalyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.arrow_forward
- Practice 4 a. Draw the more stable chair conformer of cis-1-ethyl-2-methylcyclohexane. b. Draw the more stable chair conformer of trans-1-ethyl-2-methylcyclohexane. c. Which is more stable, cis-1-ethyl-2-methylcyclohexane or trans-1-ethyl-2-methyl- cyclohexane?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 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?arrow_forward9. 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_forward
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