5.Relative Rates and Stereochemistry ((a)For the following sets of substitution reactions, draw the major organic product(s) withthe stereochemistry indicated, and indicate which reaction occurs at the faster rate. If twoconfigurational isomers form in similar amounts, draw both.(i) Substitution via SN2 mechanism (same expected product(s) for both, can draw once)CH3OCH3OH3C.CH3CH3CH3OH3C.CH3(ii) Substitution via SN1 mechanismH3COH3C.CH3OHH3CH3CHCH3OH

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Answered: 5. Relative Rates and Stereochemistry (…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.31P

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3) Draw the structures of the major organic product(s) for the following reactions. HI in CH₂Cl₂ 3 excess Cl₂ in H₂O H₂SO4 in H₂O (Two products) Br-Cl in THF 1) BH3 2) alkaline H₂O₂ OSO4 + HOOH
Draw the alkene structure that produced the following compounds in a ozonolysis reaction as specified. 1. O3 2. (CH3)2S You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one.
a) Draw the mechanism, using good curved arrow notation, for the reaction of 2-methyl-2- butene with bromine in water, omitting any stereochemistry: b) (R)-3-butyn-2-ol is treated with 2 mol of HBr, yielding optically active Compound A (C4H8OBr2). Draw the structure of the reaction with the correct stereochemistry. c) Name Compound A above, including stereochemistry. d) Compound A is treated with HBr to yield Compound B (C4H7Br3). The resulting solution is optically inactive. Draw the product(s) obtained and explain why there is a loss in optical activity.
For the following sets of substitution reactions that occur via an SN2 mechanism, draw the main organic substitution product (i.e., not the leaving group, for each reaction draw the product, though the products may be equivalent) and indicate which reaction occurs at the faster rate. (a) H3C CH₂O H3C E H3C Br (b) Br CH3O H3C + H3C-Br CH3O- H3C-Br
Predict the -elimination product(s) formed when each chloroalkane is treated with sodium ethoxide in ethanol. If two or more products might be formed, predict which is the major product.
6. Provide the line structure of product E in the following reaction. Include stereochemistry for product E as indicated. No mechanism is required. C2 H20 CH,C2 Draw any enantiomer (Include stereochemistry)
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Answer b and c only
d) e) b) c) E₂ d) Es in the products. Include stereochemistry where relevant. CH₂₁ CH₂ 1. BH, 2. H₂O₂ OH 100⁰ CH₂OH NaCN 1.0₂ 2. Zn, H H₂O* H, heat.
Q3. 2-Bromopentane, when treated with alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant? Q4 Which statement below about Sn1 reactions is incorrect? (A) Syl reactions are stepwise and have intermediates. (B) The slow step in a Sy1 reaction is formation of the carbocation intermediate. (C) Sx1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a Sy1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates. Q5 would you rank their likely order of formation from most likely to least likely? If the alkenes below were possible products of an elimination reaction, how R R R R R R R R II II IV V (А) І, V, IШ, П, IV (В) IV, II, П, І, V (С) V, I, I, П, IV (D) IV, I, Ш, І, V (E) II, П, І, V, IV
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