Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group?
(b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.
4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane.
(b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the
carbon-3 to carbon-4 bond.
(c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation
that you drew as a sawhorse representation.
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
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. 3LGPCh. 5 - Prob. 2QCh. 5 - Prob. 3QCh. 5 - Prob. 4QCh. 5 - Select the words that best describe what happens...Ch. 5 - Prob. 6QCh. 5 - Prob. 7QCh. 5 - Prob. 8QCh. 5 - 5.9 Which is untrue about the following...Ch. 5 - Prob. 10Q
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- (a) How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.arrow_forward(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 = ethylarrow_forwardDraw the most stable conformation of cis-1-tert-butyl-3-ethylcyclohexane. (a) (b) trans-1-tert-butyl-2-methylcyclohexane. (c) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.arrow_forward
- Sight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forward(a) Convert each chair cyclohexane to a hexagon with wedges and dashed wedges. (b) Draw a stereoisomer of each compound in its more stable chair conformation.arrow_forward(c) Draw the most likely conformations of the following compounds H and J and explain your reasoning. Ph OMe H Br OH CO₂Me Jarrow_forward
- 1.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_forwardFor each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers will be both equatorial in one chair conformer and both axial in the other (A) or one equatorial and one axial in each of the chair conformers (B): Drag the appropriate items to their respective bins.arrow_forwardQ2: If you think you know your definitions, try this difficult problem. (a) Draw all the stereoisomers of 2,3.4-tribromonentane, (Using Fischer projections may helpful.) You should find two meso structures and one pair of enantiomers. (b) Star (*) the asymmetric carbon atoms, and label each as (R) or (S). (c) In the meso structures, show how C3 is pot asymmetric, nor is it a chiral center, Yetn stereocenter. (d) In the enantiomers, show how C3 is not a stereocenter.arrow_forward
- Draw 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(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.arrow_forwarddraw the most stable conformation of (a) ethylcyclohexane (b) 3-isopropyl-1,1-dimethylcyclohexanearrow_forward
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