Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 57P
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-isopropylcyclohexane
- c. trans-1-ethyl-2-methylcyclohexane
- d. cis-1,2-diethylcyclohexane
- e. cis-1-ethyl-3-isopropylcyclohexane
- f. cis-1-ethyl-4-isopropylcyclohexane
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Draw 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-isopropylcyclohexane
Draw all the stereoisomers for each of the following:
a. 1-chloro-3-methylpentane
b. 2-methyl-1-propanol
c. 2-bromo-1-butanol
d. 3-bromo-2-butanol
e. 3,4-dichlorohexanef. 1,2-dichlorocyclobutane
g. 1,3-dichlorocyclohexane
h. 1,4-dichlorocyclohexane
i. 1-bromo-2-chlorocyclobutane
j. 1-bromo-3-chlorocyclobutane
CH₂
CH₂CH3
The correct name for the compound given above is
Select one:
O a. 1-propyl-3-ethyl-4-methylbenzene
b.
4-cyclopropyl-2-ethyl-1-methylbenzene
O c. p,o-methylethylcyclopropylbenzene
O d. 1-propyl-3-ethyl-4-methylcyclohexane
Chapter 3 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Draw the structure for each of the following...Ch. 3.1 - Name the following compounds:Ch. 3.1 - Prob. 7PCh. 3.2 - What is each compounds systematic name?Ch. 3.2 - Prob. 11PCh. 3.3 - Prob. 12PCh. 3.3 - Convert the following condensed structures into...Ch. 3.3 - The molecular formula for ethyl alcohol (CH3CH2OH)...
Ch. 3.3 - Draw a condensed and a skeletal structure for the...Ch. 3.3 - What is each compounds systematic name?Ch. 3.4 - Prob. 17PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.5 - Are the following compounds primary, secondary, or...Ch. 3.5 - Name the following amines and tell whether they...Ch. 3.5 - Draw the structures and provide systematic names...Ch. 3.6 - Predict the approximate size of the following bond...Ch. 3.7 - What is the smallest straight-chain alkane that is...Ch. 3.7 - Prob. 24PCh. 3.7 - Prob. 25PCh. 3.7 - Prob. 26PCh. 3.7 - List the compounds in each set from highest...Ch. 3.8 - Rank the following compounds in each set from most...Ch. 3.8 - In which solvent would cyclohexane have the lowest...Ch. 3.8 - Prob. 30PCh. 3.9 - Prob. 31PCh. 3.9 - a. Draw the three staggered conformations and the...Ch. 3.9 - a. Draw the most stable conformation of pentane...Ch. 3.11 - Draw 1,2,3,4,5,6-hexachlorocyclohexane with a. all...Ch. 3.12 - At any one time, would you expect there to be more...Ch. 3.13 - Prob. 36PCh. 3 - a. How many hydrogens does an alkane with 17...Ch. 3 - Prob. 2PCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 39PCh. 3 - Prob. 40PCh. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Name the following amines and tell whether they...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - What is each compounds name? a. CH3CH2CH2OCH2CH3Ch. 3 - Draw the structural formula for an alkane that has...Ch. 3 - Which has a. the higher boiling point:...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 51PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - Prob. 53PCh. 3 - For rotation about the C-3 8 C-4 bond of...Ch. 3 - Prob. 55PCh. 3 - What is each compounds systematic name?Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Draw the nine constitutional isomers with...Ch. 3 - Prob. 59PCh. 3 - Prob. 60PCh. 3 - Prob. 61PCh. 3 - Using Newman projections, draw the most stable...Ch. 3 - For each of the following disubstituted...Ch. 3 - Prob. 64PCh. 3 - Prob. 65PCh. 3 - What is each compounds systematic name?Ch. 3 - Prob. 67PCh. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Prob. 69PCh. 3 - Prob. 70PCh. 3 - a. Draw a potential energy diagram for rotation...
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- 11. Which of the following is the IUPAC name of the compound below? Select one: O a. 2-cyclopropyl-1-methylcyclopentane O b. 1-methyl-2-cyclopropylcyclopentane c. 2-cyclopropyl-1-methylpentane O d. 1-methyl-2-cyclopropylpentane 12. Which of the following is the common name of the compound below? Select one: O a. 2,2-dimethylpentane O b. 1-isobutylpropane c. neopentane O d. neoheptanearrow_forward• Draw the chair conformations of the following compounds and determine which geometric isomer is more stable. Also show using Newman projection that one conformation is more stable than the other. a. cis-1-isopropyl-2-methylcyclohexane b. 1-methycyclohexanearrow_forward4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forward
- draw in skeletal form:arrow_forwardDraw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description. a.a 1,1-disubstituted cyclohexane with an axial CH3CH2 group b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 group.arrow_forwardDraw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description. a. a 1,1-disubstituted cyclohexane with an axial CH3CH2 group b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 grouparrow_forward
- 1. What orbitals (around Carbon) are used to form each bond in the following molecules: A. CH3CH3 B. CH2CH2 2. Draw the structure corresponding to each IUPAC name: 3-ethyl-1,1-dimethylcyclohexane, 6-isopropyl-2,3-dimethylnonanearrow_forwardThe correct IUPAC name for this compound is: Oa. O a. cis-1,5-dicyclohexyl-1-pentene O b. trans-1,5-dicyclohexyl-1-pentene trans-1,5-diphenyl-1-pentene O d. cis-1,5-diphenyl-1-pentenearrow_forwardDraw the chain conformer of a) the most stable conformer of isopropylcyclohexane b) the most stable conformer of cis-1-tert-butyl-4-methylcyclohexanearrow_forward
- #544 of Isomers (chiral) Which of the following 2-chloro-1-butanol (A), 3-chloro-1-butanol (B), and 4-chloro-1-butanol (C), contain a stereogenic carbon atom. Select one: a. A only O b. B only O c. C only O d. A and B e. A, B and Carrow_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_forward1,2-ditert-butylcyclohexane is an interesting case of a conformational study. The cis isomer is more stable than the trans isomer, although the trans isomer presents a conformer with both substituents in equatorial positions. In order to analyze this fact:a. Draw the conformational equilibrium of both compounds. Explain using and drawing the structures why this difference happens (the one described above). b. In the trans isomer, the di-axial conformation is 25.9 kJ / mol more stable than the di-equatorial. Calculate the energy of the di-equatorial conformation.arrow_forward
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