9. For each of the following formulas, identify every structural isomer containing one or morestereocenters, give the number of stereoisomers for each, and draw and fully name at least one of thestereoisomers in each case. (a) C7H16 (b) C3H18 (c) C5H10, with one ring.10. Assign the appropriate designation of configuration (R or S) to the stereocenter in each of thefollowing enantiomers. (Hint: Regarding cyclic structures containing stereocenters, treat the ring as ifit were two separate substituents that happen to be attached to each other at the far end of themolecule look for the first point of difference, just as you would for acyclic structures.)H,Cн, он(b)CI H(c)(a)(d)HBrOHH.(e)(f) C(g)(h)HC HHC H(i)CH,NH,OCH,CH,O11. For each of the following questions, assume that all measurements are made in 10-cm polarimetersample containers. (a) A 10-mL solution of 0.4 g of optically active 2-butanol in water displays anoptical rotation of 20.568. What is its specific rotation? (b) The specific rotation of sucrose (commonsugar) is 166.4. What would be the observed optical rotation of such a solution containing 3 g ofsucrose? (c) A solution of pure (S)-2-bromobutane in ethanol is found to have an observed a 5 57.38.If [a] for (S)-2-bromobutane is 23.1, what is the concentration of the solution?12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, isthe 1R,2S,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part(b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S,2R,5R-stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the15,25,5R-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding ofthe conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from moststable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?

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For each of the following formulas, identify every structural isomer containing one or more stereocenters, give the number of stereoisomers for each, and draw and fully name at least one of the stereoisomers in each case. (a) C7H16 (b) C8H18 (c) C5H10, with one ring.

For each of the following formulas, identify every structural isomer containing one or more stereocenters, give the number of stereoisomers for each, and draw and fully name at least one of the stereoisomers in each case. (a) C7H16 (b) C8H18 (c) C5H10, with one ring.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomers
4. Draw all possible stereoisomers of the following compounds. Assign the appropriate absolute (R/S) or geometric (E/Z) configuration to each of the stereoisomers (or double bonds) and label pairs enantiomers, diastereomers and meso compounds. (a) CH3CHBRCHOHCH3 (c) CH3CH=C(Br)CH=CHCI (e) CH3CH₂CHOHCHOHCH2CH3 (g) OH НО... CI (h) H3C Br (b) CH3CHBRCHBRCH ₂Br (d) CH3CH(C6H5)CHOHCH3 (f) CH₂(OH)CH2-CH(OH)CH=CHOH CH3 (1) Br HS Br
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1. (a) The following hypertension drug is sold as the single (S,S,S) isomer. OH i. Identify the three asymmetric carbon centers in the molecule and draw the structure of the S,S,S stereoisomer using hatched lines and wedges. Include your assignments of priorities. ii. Draw the structure of the enantiomer of the compound you drew in part (i) and assign R or S configuration to the chiral centers.
8. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) H3C c) CH3 Br H. CH3 Br Br CH3 H. CI Holl H Cill Cl- CH3 Br H. CI CH3 HO. H. H3C Cl H3C- H- H. CH3 Cl a) b) c) 9. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) c) CH2CH3 NH2 HO CH3 H3C. CH3 Cl HO H;C CH2CH3 F. F H;C. CI H H,N -CH3 CH3 NH2 H3C Br H2N C1 H3C CH3 CH3 H;CH,C- Cl F H. H Br CH,CH3 CH3 a) b) c)
(−)-Menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol and has the R configuration at the hydroxyl-substituted carbon. (a) Draw the preferred conformation of (−)-menthol. (b) (+)-Isomenthol has the same constitution as (−)-menthol. The configurations at C-1 and C-2 of (+)-isomenthol are the opposite of the corresponding chirality centers of (−)-menthol. Write the preferred conformation of (+)-isomenthol.
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Copy the structure and mark all stereocenters in each molecule and tell how many stereoisomers are possible for each Letter d, e and f only.
12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?
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8) For each of the pairs of molecules drawn below, place letters in the corner boxes corresponding to all accurate descriptions of the relationship between the two molecules. a) b) c) HO F A enantiomers F all letters that apply H H OH Вад CI all letters that apply all letters that apply B diastereomers C different conformations of the same molecule D identical conformations of the same molecule E constitutional isomers F stereoisomers G different molecules H both are chiral I neither is chiral