Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 5, Problem 29PP
Practice Problem 5.29
Write formulas for all of the isomers of each of the following. Designate pairs of enantiomers and achiral compounds where they exist.
(a) 1-Bromo-2-chlorocyclohexane
(b) 1-Bromo-3-chlorocyclohexane
(c) 1-Bromo-4-chlorocyclohexane
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2.35
Write a structural formula for each of the following compounds:
(a) 6-Isopropyl-2,3-dimethylnonane
(b) 4-tert-Butyl-3-methylheptane
(c) 4-Isobutyl-1,1-dimethylcyclohexane
(d) sec-Butylcycloheptane
(e) Cyclobutylcyclopentane
If either of the following molecules has a stereogenic carbon (chirality center), give structures for both of the enantiomers.
(a) 2-bromopropane (b) 2-bromobutane
Write the two chair conformations of each of the following and in each part designate whichconformation would be the more stable: (a) cis-1-tert-butyl-3-methylcyclohexane, (b) trans-1-tert-butyl-3-methylcyclohexane, (c) trans-1-tert-butyl-4-methylcyclohexane, ( d) cis-1-tert-butyl-4-methylcyclohexane.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 1PPCh. 5 - Prob. 2PPCh. 5 - Prob. 3PPCh. 5 - Prob. 4PPCh. 5 - Prob. 5PPCh. 5 - Prob. 6PPCh. 5 - Prob. 7PPCh. 5 - Practice Problem 5.8 Write three-dimensional...Ch. 5 - Prob. 9PPCh. 5 - Prob. 10PP
Ch. 5 - Practice Problem 5.11 List the substituents in...Ch. 5 - Prob. 12PPCh. 5 - Practice Problem 5.13 Tell whether the two...Ch. 5 - Prob. 14PPCh. 5 - Prob. 15PPCh. 5 - Prob. 16PPCh. 5 - Prob. 17PPCh. 5 - Prob. 18PPCh. 5 - Prob. 19PPCh. 5 - Prob. 20PPCh. 5 - Practice Problem 5.21 The following are formulas...Ch. 5 - Practice Problem 5.22 Write three-dimensional...Ch. 5 - Prob. 23PPCh. 5 - Practice Problem 5.24 Give names chat include (R)...Ch. 5 - Prob. 25PPCh. 5 - Prob. 26PPCh. 5 - Prob. 27PPCh. 5 - Prob. 28PPCh. 5 - Practice Problem 5.29 Write formulas for all of...Ch. 5 - Prob. 30PPCh. 5 - Prob. 31PPCh. 5 - Prob. 32PPCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - 5.35 Designate the (R) or (S) configuration at...Ch. 5 - Prob. 36PCh. 5 - (a) Write the structure of...Ch. 5 - Shown below are Newman projection formulas for...Ch. 5 - 5.39 Write appropriate structural formulas...Ch. 5 - Discuss whether each of the following compounds...Ch. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Compound F has the molecular formula C5H8 and is...Ch. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - For the following molecule, draw its enantiomer as...Ch. 5 - 5.49 (Use models to solve this...Ch. 5 - 5.50 (Use models to solve this...Ch. 5 - (Use models co solve this problem.) Write...Ch. 5 - 5.52 Tartaric acid was an important compound in...Ch. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 1LGPCh. 5 - Prob. 2LGPCh. 5 - Prob. 3LGP
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- 5.76 2,3-Dibromoprop-1-ene (C3H4Br₂) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule with the formula C3H3Br₂Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br₂Cl; (b) enantiomers of C3H3Br₂Cl; (c) diastereomers of C3H3Br₂Cl. co 11 HHH Juods H Brugtrio 2 bas A 2,3-Dil so ontemme A chon Br 2,3-Dibromoprop-1-enearrow_forward(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward
- Given each of the IUPAC names provided, draw the corresponding structure.(a) 2,4-dicyclopropyl-2-ethoxyhexane(b) 1,2-dichloro-1-(2-methylpropyl)-4-nitrocyclohexane(c) 1,3-dicyclopentyl-1,2,3,4-tetramethoxycyclooctane(d) 1-cyclobutyl-4-(1,1-dimethylethyl)-2,4-dinitrononane(e) 1-(1,1-dimethylbutyl)-2-ethoxy-1,2,3-trinitrocyclobutane(f) 1,2,4-tricyclopropyl-1-(2,2-dichloropentyl)cyclohexane(g) 4-(2-chloro-1-methoxyethyl)-1,1-dinitroheptane(h) 3,3,4-trichloro-1-cyclohexoxy-4-(1,1-dichloroethyl)decanearrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward2.35 Consider 1-bromo-2-methylpropane and draw the following.(a) The staggered conformation(s) of lowest energy(b) The staggered conformation(s) of highest energyarrow_forward
- Give answer to all parts?arrow_forwardFor each of the following disubstituted cyclohexanes, determine whether the cis or trans isomer is more stable. (a) (b) (c)arrow_forwardDraw a bond-line diagram for the compounds below. Which of the following compounds is chiral? (a) 2-bromobutane (b) methylcyclohexane (draw a chair configuration)arrow_forward
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