The structure of A is shown below. Но з -CH2CH=CH2 A (1) Predict the possible number of stereoisomers A can have. (ii) Draw the 3D structure of the (2S, 3R, 55) enantiomer showing its correct stereochemistry. (iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 5S) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R) enantiomer. Given the specific rotation of the mixture = +4.8°.

The structure of A is shown below. Но з -CH2CH=CH2 A (1) Predict the possible number of stereoisomers A can have. (ii) Draw the 3D structure of the (2S, 3R, 55) enantiomer showing its correct stereochemistry. (iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 5S) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R) enantiomer. Given the specific rotation of the mixture = +4.8°.

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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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
Consider the reaction between (1S,3S)-1-chloro-3-methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. -SH C NaOH Draw only the organic product. Select /// Draw Rings More C H S Erase:
(−)-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.
1) In the following reactions, give the nature and possibly the stereochemistry of A1, A2 and B and justify the proportions obtained. 4 1=3 |=1 CI ull OH KOtBu 3 DMSO H₂SO4 majority A1 A1 + 2)When the first compound is treated with MeONa in methanol, compounds A1 and B are also obtained, as well as a higher molecular weight compound C, which has a higher molecular weight. B are also obtained as well as a higher molecular weight compound C whose 1H NMR spectrum is given below. Justify the formation of C. 2 PPM equimolar mixture + isomere of A1 1=3 mobilie B A2 1=3 1=3 1 1=3 O
Consider the E2 elimination of Compound A, and answer the following questions: (a) Label each stereocenter in Compound A with the correct R or S configuration. (b) Draw the structures of the major product with correct stereochemistry. Assume D and H have the same reactivity.
5. Given the following structure: (a) Draw all the stereoisomers; CH2 OH (b) Identify all of the enantiomeric and diastereomeric pairs; (c) Assign R or S configuration at each asymmetric carbon for each structure. Justify your assignments for the original structure (above).
Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you. (a) ОН (b) (c) NH, ОН СH—CH—СООН | pentan-2-ol pentan-3-ol alanine (d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane (h) (i) H CH; "H H. H CH, H
(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.
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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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