HH1. CH3MgBr(d)'OHH2. H3O+CH3CH3H₂O(e)H3C-C-BrCH3H₂C-C-OHCH3refluxCH3+HBr2. Draw the product(s) of this reaction?H3C CH3CH3CHCBrCH3COHJOHheatCH2CH3 1. Study the following reactions and draw their reaction mechanisms(a)CH3CH2CH2ClAICI 3CH2CH2CH3(b)CH3CH2CCIAlCl3CH2CH3(c)BrH1. 1% NaOH, H₂OHO HOHH₂C2. H₂O*H₂C(substance A)(substance B)H CH3-CH3What is the stereochemistry of the chiral carbon in substance A?Ans.What is the stereochemistry of the chiral carbon in substance B?Ans.

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Answered: H H 1. CH3MgBr (d) 'OH H 2. H3O+ CH3…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter5: Stereochemistry At Tetrahedral Centers

Section5.SE: Something Extra

Problem 70AP

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18 Mark each stereocenter in these molecules with an asterisk. Note that not all contain stereocenters. (a) OH CH, N. `CH3 (b) OH (c) HO, NH2 (d)
There are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas for these isomers. (b) Which of the isomers are chiral? (c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas chromatography, how many fractions would be obtained and which compounds would each fraction contain? (d) How many of these fractions would be optically active? tod o ors brie page 10 of 17
Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB, or E2: (a) CH3CH₂CH₂CH₂Br NaN3 THF CH3CH₂CH₂CH₂N=N=N (b) (c) (d) CI CH3CH₂CHCH₂CH3 KOH Ethanol -CH3 CH3CO₂H OH NaOH Ethanol CH3CH₂CH=CHCH3 요 OCCH3 -CH3
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).
Which of these compounds is expected to be optically active at room temperature? ÇOOH H OH CH, CH, Br но- Br CH H- OH COOH CH (A) (B) (C) (D) O B OD O A
A chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.
(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.
Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?
(d) EtO 1. Name each compound, showing stereochemistry where relevant: (a) Ph Ph (b) CH3(CH2);CN (c) NHCH, (d) EtO OEt (e) CI Cl
For the following molecules, draw all possible stereoisomers using line-angle formulas with wedge/dash notation. Label the stereocenters as R or S. Indicate which ones are enantiomers and which ones are diastereomers. (Remember: there are 2 stereoisomers possible for a molecule with n chiral centers) (A) (B) (C) (1 chiral center) Br OH (2 chiral centers) CI OH CH3 (3 chiral centers)
(a) meso-hexane-3,4-diol, CH3CH2CH(OH)CH(OH)CH2CH3, draw any diastereomers.
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. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)

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