Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 5.10A, Problem 5.17P
Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.
- a. (S)-propane-1,2-
diol - b. (R)-2-bromobutan 1-ol
- c. (S)-1,2-dibromobutane
- d. (R)-butan-2-ol
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a. Draw the two chair conformers for each of the stereoisomers of trans-1-tert-butyl-3-methylcyclohexane. b. For each pair, indicate which conformer is more stable.
a. Using the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. b. From the nine stereoisomers, identify one pair of enantiomers. c. Draw the most stable conformer of the most stable stereoisomer.
Glucose is a simple sugar with five substituents bonded to a sixmembered ring.a.Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.
b.Convert this representation to one that uses a hexagon with wedges and dashed wedges.
c.Draw a constitutional isomer of glucose.
d.Draw a stereoisomer that has an axial OH group on one carbon.
Chapter 5 Solutions
Organic Chemistry (9th Edition)
Ch. 5.2 - Determine whether the following objects are chiral...Ch. 5.2A - Prob. 5.2PCh. 5.2B - Prob. 5.3PCh. 5.2B - Prob. 5.4PCh. 5.2C - Prob. 5.5PCh. 5.3 - Prob. 5.6PCh. 5.3 - Prob. 5.7PCh. 5.4D - Prob. 5.8PCh. 5.4D - Prob. 5.9PCh. 5.4D - Prob. 5.10P
Ch. 5.5 - Prob. 5.11PCh. 5.7 - When optically pure (R)-2-bromobutane is heated...Ch. 5.7 - Prob. 5.13PCh. 5.8 - Prob. 5.14PCh. 5.9B - Draw three-dimensional representations of the...Ch. 5.10A - For each sot of examples, make a model of the...Ch. 5.10A - Draw a Fischer projection for each compound....Ch. 5.10B - Prob. 5.18PCh. 5.10C - For each Fischer projection, label each asymmetric...Ch. 5.11C - Prob. 5.20PCh. 5.13 - Prob. 5.21PCh. 5.13 - Prob. 5.22PCh. 5.15 - Prob. 5.23PCh. 5.16A - Prob. 5.24PCh. 5 - The following four structures are naturally...Ch. 5 - For each structure, 1. star () any asymmetric...Ch. 5 - Prob. 5.27SPCh. 5 - Prob. 5.28SPCh. 5 - Prob. 5.29SPCh. 5 - Prob. 5.30SPCh. 5 - Prob. 5.31SPCh. 5 - Prob. 5.32SPCh. 5 - Prob. 5.33SPCh. 5 - Prob. 5.34SPCh. 5 - For each structure, 1. draw all the stereoisomers....Ch. 5 - Prob. 5.36SPCh. 5 - Prob. 5.37SPCh. 5 - 3,4-Dimethylpent-1-ene has the formula...Ch. 5 - A graduate student was studying enzymatic...Ch. 5 - Prob. 5.40SPCh. 5 - Prob. 5.41SP
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- • Question 5: Label each stereogenic center as R or S. CH₂ a. CH₂CH₂ b. CH H 1 NH₂ H CH3 CH₂CH₂ T C. D CI CH3 d. Br C ICH₂ H e. f. H* HO C HOOC CH₂ HO CH(CH3)2 -C₂ C CH3 SH NH₂ H CH3 g. h. .CI CIarrow_forwardGlucose is a simple sugar with five substituents bonded to a six-membered ring.a. Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.b. Convert this representation into one that uses a hexagon with wedges and dashed wedges.c. Draw a constitutional isomer of glucose.d. Draw a stereoisomer that has an axial OH group on one carbon.arrow_forward6. Indicate whether the circled carbon in each of these is chiral a. CH3-CH-CH2-CH3 b. CH3-CH2-C-CH3 Cl c. CH3-CH2-CH-OH d. Br CH2 ©H H,C CH2 CH3 HC. CH2 Br CHarrow_forward
- 3.A carbon atom that is bonded to four different groups is a/an A.achiral center B.chirality center C.symmetrical center D.symmetrical centerarrow_forwardConsider CH3-CH(OH)-CH(OH)(Br). a.How many stereogeniccenters are in the molecule? b.How many stereoisomers are there for the compound? c.Draw the Fischer projection for each of the stereoisomer. Label each using I, II, etc. d.Which pairs are enantiomers? Which are diastereomers? e.Determine the absolute configuration of each chiral center in one pair of diastereomer.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_forward
- Draw 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_forwardConsider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. 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_forwardUsing the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. A. From the nine stereoisomers, identify one pair of enantiomers. B. Draw the most stable conformer of the most stable stereoisomer.arrow_forward
- Consider cis-1,2-dibromocyclohexane and trans-1,2-dibromocyclohexane. anleune Draw these two compounds in wedge-dash representation. a. b. Which compound is considered to be meso? C. Which is chiral? mer d. Provide the structure for the (S, S) isomer of your answer to part c. in two its two chair conformations and circle the more stable conformational isomer.arrow_forwardThis is one enantiomer of the molecule. OH H CCH2-CH2-CH3 CH3 Draw the structure of the other enantiomer using wedges and dashes. Click and drag to start drawing a structure.arrow_forwardMatch the pairs of compounds with the type of isomerism a. functional isomer b. skeletal isomer c. positional isomer d. cis, trans configuration e. diastereomer f. e,z, configuration g. enantiomerarrow_forward
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