compound 3,4-dimethyl-hexan-3-ol of 3R, 4S configuration is treated with a concentrated HBr solution at room temperature. A mixture of two stereoisomers is obtained. If the reaction mixture above is heated, the appearance of several other compounds is observed. 1) Draw the different compounds obtained using the wedge-flywheel representation. 2) What is the majority product? Explain 3) Propose a modification of the experimental conditions in order to obtain the exclusive formation of these compounds obtained after heating

compound 3,4-dimethyl-hexan-3-ol of 3R, 4S configuration is treated with a concentrated HBr solution at room temperature. A mixture of two stereoisomers is obtained. If the reaction mixture above is heated, the appearance of several other compounds is observed. 1) Draw the different compounds obtained using the wedge-flywheel representation. 2) What is the majority product? Explain 3) Propose a modification of the experimental conditions in order to obtain the exclusive formation of these compounds obtained after heating

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

See similar textbooks

Similar questions

Acid-catalyzed bromination of pentan-2-one (CH3COCH2CH2CH3) forms two products: BrCH2COCH2CH2CH3 (A)and CH3COCH(Br)CH2CH3 (B). Explain why the major product is B, with the Br atom on the more substituted side of the carbonyl group.
The alkene shown undergoes bromination. (a) Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge‑and‑dash bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center has one. (b) Characterize the starting alkene as having the E or Z configuration. (c) characterize the product(s).
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1- phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Whichproduct predominates—the product of inversion or the product of retention of conguration? (c) Suggest an explanation for this phenomenon.
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenyl-1-propanol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates-the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon. H Br он H20 1-bromo-1-phenylpropane 1-phenyl-1-propanol observed [a) = +5.0 optically pure S isomer, [a] =-48 %3D
The alkene shown undergoes bromination. H (a) Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge-and-dash bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center has one. (b) Characterize the starting alkene as having the E or Z configuration. (c) characterize the product(s). (a) H Br₂ Draw the product(s) of bromination. Br H Br
In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that does not occur?
Optical active compound 1-chloro-3-methylcyclopentane was reacting withpotassium t-butoxide in t-butanol. Two alkene products were obtained. Themain product was optically active, and the secondary product was notoptically active. What are the two products?
a) Draw both chair conformations of the starting alkyl bromide. Indicate which conformation, if either is more stable. Briefly justify your answer. b) The starting alkyl halide has two chiral carbons. What are the configurations (R/S) at each of these carbons? c) Identify the mechanism (E1/E2) which reactions 1, 2, and 3 proceed by. d) Provide mechanisms that explain the products formed in reactions 1, 2, and 3. All electron movement must be shown in order to receive full credit. e) Indicate which product is the major and which product is the minor in reactions 2 and 3. Briefly justify your answer.
a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?
Account for the regioselectivity and stereoselectivity observed when this compound is treated with Br2 in H₂O by drawing the final product in the reaction. • Use wedge and hash bonds ONLY when needed to show reaction stereochemistry. • If the reaction produces a racemic mixture, just draw one stereoisomer.
a) Considering compounds 2a through 21, identify: ONE PAIR of geometric isomers; TWO PAIRS of enantiomers and THREE PAIRS of identical molecules. b) Give the names, including the configurations, of each of the geometric isomers and of each of the enantiomers. Draw the relevant structures in the space provided in the Answer Booklet. c) Sort compounds 2a, 2b, 2c, 2f and 2k in order of increasing solubility in water and briefly justify your ordering. 2 НО. AH H H anulta HOwno barwolset of ef 28nuor OH 2bc 2c ning) bi 10291 H WH 2 st brbot di OH Lacenoqoid OH to nabio ni one nt at dit st 2e OH "H OH bre 2a 2d 2g 2j H HO 2h 2k HO ...H di al nt o 2f 2i 21