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 38P
Shown below are Newman projection formulas for (R,R)-, (S, S)-, and (R, S)-2,3-dichlorobutane. (a) Which is which? (b) Which formula is a meso compound?
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(a) which if the structure of trans-1,2-dimethylcyclopentane?
(b) which is the most stable conformation of 1-bromo-2-ethylcyclohexane?
(c) which is the least stable conformation of 1-bromo-2-ethylcyclohexane?
(d) which is the more stable configuration of 1,3-dimethylcyclopentane?
*Et = ethyl
Draw the planar (Haworth) structure for cis-1-ethyl-2- methylcyclohexane. (b) Draw the two ring - flipped chair conformations. (c) Circle the more stable chair conformation (circle both if they are equal in energy). Draw the Haworth structure and the two ring-flipped conformations of 1, 2, 4- trimethylcyclohexane (Compound D) on the frames below, b) Circle the more stable chair conformation (circle both if they are equal in energy). Haworth Structure
(a) Draw all the stereoisomers of 2,3,4-tribromopentane. (Using Fischer projections may be
Q2: If you think you know your definitions, try this difficult problem.
helpful.) You should find two meso structures and one pair of enantiomers.
(b) Star (*) the asymmetric carbon atoms, and label each as (R) or (5).
(c) In the meso structures, show how C3 is pot asymmetric, nor is it a chiral center, yet it is a
stereocenter.
(d) In the enantiomers, show how C3 is not a stereocenter.
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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- (v) Identify every chiral center in cholesterol (below) with an asterisk. HO (vi) Draw an energy vs. dihedral angle diagram that represents all the conformations of butane starting from the anti-conformation. (vii) Draw both chair conformations for the compound shown below using the templates provided. Circle the chair conformation that is lowest in energy. Br (viii) Draw a chair conformation that meets the following criteria. Axial chlorine at C5 Equatorial methyl at C4 Bromine on C2 that is cis to the chlorine 6 2 5 3 4arrow_forwardQ1: Draw the structure of each of the following molecules: (a) (R)-1-chloro-1-fluorobutane (c) (2R,3S)-3-Bromo-2-chloro-1-pentanol (b) (S)-2-chloropentane; (d) (R)-2,2,3-trichlorobutane.arrow_forward(a) Draw the possible Newman projection(s) for the GAUCHE conformation of the C3-C4 bond in 2-methylpentane. (b) Give the IUPAC name for the following compound, including the R,S designation for each stereogenic center.arrow_forward
- (a) Draw all the stereoisomers of 2,3,4-tribromopentane. (Using Fischer projections may be Q2: If you think you know your definitions, try this difficult problem. helpful.) You should find two meso structures and one pair of enantiomers. (b) Star (*) the asymmetric carbon atoms, and label each as (R) or (5). tej in the meso structures, show how C3 is not asymmetric, nor is it a chiral center, yet it is a stereocenter. (d) In the enantiomers, show how C3 is not a stereocenter.arrow_forwardShown below are Fischer projection formulas for (R,R)-, (S,S)-, and (R,S)-2,3-dichlorobutane.arrow_forward1.Draw both cis- and trans-1,4-dimethylcyclohexane in their conformations. (a) How many stereoisomérs are there of cis-1,4-dimethylcyclohexane, and how many of rans-1,4-dimethylcyclohexane? (b) Are of the structures chiral? (c) What are the stereochemicar relationships among the various stereoisomers of 1,4-dimethylcyclohexane?arrow_forward
- For the following pairs, circle the most appropriate classificationarrow_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(a)(2R,3S)-2,3-dibromohexane, draw any enantiomer.arrow_forward
- (a) Draw all possible stereoisomers of 4-methylnon-2-ene, and name each isomer, including its E,Z and R,S prexes. (b) Label two pairs of enantiomers. (c) Label four pairs of diastereomers.arrow_forward(b) (d) CH3 CH3CHCH₂CH₂CH₂Br SCH₂CH3 1. (NH₂)₂C=S 2. NaOH, H₂O H₂O2, H₂O, ? ?arrow_forward(a) Draw all possible stereoisomers of 4-methylnon-2-ene, and name each isomer, including its E,Z and R,S prefixes. (b) Label two pairs of enantiomers. (c) Label four pairs of diastereomers.arrow_forward
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