5. Relative Rates and Stereochemistry ( (a) For the following sets of substitution reactions, draw the major organic product(s) with the stereochemistry indicated, and indicate which reaction occurs at the faster rate. If two configurational isomers form in similar amounts, draw both. (i) Substitution via SN2 mechanism (same expected product(s) for both, can draw once) CH3O CH3O H3C. CH3 CH3 CH3O H3C. CH3 (ii) Substitution via SN1 mechanism H3CO H3C. CH3OH H3C H3C H CH3OH

5. Relative Rates and Stereochemistry ( (a) For the following sets of substitution reactions, draw the major organic product(s) with the stereochemistry indicated, and indicate which reaction occurs at the faster rate. If two configurational isomers form in similar amounts, draw both. (i) Substitution via SN2 mechanism (same expected product(s) for both, can draw once) CH3O CH3O H3C. CH3 CH3 CH3O H3C. CH3 (ii) Substitution via SN1 mechanism H3CO H3C. CH3OH H3C H3C H CH3OH

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.27P: Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both...

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Q4 Which statement below about Snl reactions is incorrect? (A) SNl reactions are stepwise and have intermediates. (B) The slow step in a Snl reaction is formation of the carbocation intermediate. (C) SNl reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a Syl reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Snl reactions as they tend to help stabilize carbocation intermediates.
4. For the following reactions, develop a transition-state structure using molecular models which would account for the observed stereoselectivity. Also, describe the type of pericyclic reactions using the proper terminology. (each Br heat A & Br b) F 0°C F heat heat d) product? =& & MeO₂C OCH3 H HO 1. CO₂Me مر CO₂Me LOCH3 heat heat MeO₂C HO
1. The conversion between alcohols, ethers, and epoxides is an important process in organic synthesis. (a) Draw a mechanism for the classic epoxidation of an alkene using MCPBA. (b) Show how this epoxidation can be converted to alcohols/ethers using both acidic and basic conditions. Be sure to highlight the difference between regio- and stereochemistry with the different reactions. (c) Name the end products and be sure to include all necessary stereochemistry. MCPBA CH3OH +H O + Diastereomer SN 1 CH₂ONa SN 2 ↓ OH OCH3 um OCH 3
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) SN1 reactions are stepwise and have intermediates. (B) The slow step in a SN1 reaction is formation of the carbocation intermediate. (C) SN1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a SN1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates.
Complete the following: Stereochemistry, enantio-, and regioselectivity are important. CrO3, H2SO4 a) OH Bromination of an alcohol (Sn2) type EtO₂C CO₂Et b) b) d) H3CO type NH2 a) b) H3CO type a) b) OH g) type CN CI h) acetone Swern Oxidation type type CO₂H type Доно i) Me3SICI, Imidazole OSiMe3 Et3N, CH2Cl2 Br type a) Mg°, THF Br j) b); H3O+ H2SO4 (H+) MeOH OMe type type
Chemistry 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (а) NaOEt heat (b) heat (c) Br NaCN DMF (d) (e) OH H,SO,/H,PO, heat (f) HBr (g) 1) BH. THE 2) H,0, OH (h) 1) Hg(OAC), H-0 2) NaBH, (i) KMNO, NaOH Cold
Draw the alkene that would react with the reagent given to account for the product formed. OH H₂SO4 CH3CH2CCH2CH3 ? + H₂O CH2CH3 . 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.
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Compounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle (Previous Next
TReview TOpics] [References Draw a structural formula for the major product of the reaction shown. CH3 CH3CHCH=CH2 Show product steréochemistry IF the reactant alkene has both carbons of the double bond within a • Do not show stereochemistry in other cases. If the reaction produces a racemic mixture, just draw one stereoisomer. C P opy aste C.
6A2: Recognize and apply the general motif of electrophilic addition via the AE the mechanistic step, including matters of regiochemistry (Markovnikov's rule) and configuration/stereochemistry (AN with a carbocation vs. syn addition) to solve synthetic problems and predict products. Add all lone pairs and provide a detailed, electron-pushing mechanism for the reaction by following the mechanistic step descriptors. You must redraw the entire sequence (that is, not just draw over the given structures) to pass this problem. HO H. .H HO TRE- + HOH H AE 1,2R OH + HOH PT + H30Ⓡ C G