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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter25: Enolate & Enol Nucleophiles

Section: Chapter Questions

Problem 7E

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3. Complete the following assigned problem from the textbook. [10 pts]
14.44 Ignoring stereoisomers, draw all products that form by addition of HBr to (E)-hexa-1,3,5-triene.
For full credit,
(E)-hexa-1,3,5-triene
•
Use 'curly arrows' to denote electron flow.
•
Show all resonance forms of the reaction intermediate(s).
Explicitly show reaction of the different resonance forms to make each product.

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Draw the reactants and complete the mechanism by drawing in the appropriate electron-flow arrows (including stereochemistry) for the following Sy2 reaction of an alkyl bromide. Represent the nucleophile as an ion. Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the grid and connecting them with bonds, including charges where needed. Indicate the mechanism by drawing the electron-flow arrows on the molecules. Arrows should start on an atom or a bond and should end on an atom, bond, or where a new bond should be created. • View Available Hint(s) + CH N H. S CH H,C C-ÖH CI HC Br HC F [1] A
Please help me with the organic chemistry problem below: Consider the reaction below: (Check the attached image) (it is between Furan and maleic anhydride, a DIels-Alder reaction) a) Will this reaction for an endo product (with a melting point of 80-81 degrees) or the exo product (with a melitng point of 114 degrees)? b) Carefully explain why the product must have been formed the way it did (exo or endo). c) Provide a mechanism for this reaction.
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Give a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2- methylpentane is heated with sodium methoxide. • Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Indicate which step is likely to be rate determining.
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Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps.
Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the reorganization of electron density. Show all intermediates, lone pairs, nonzero formal charges, countercharges, and reversibility or irreversibility. Finally, explain in detail why the observed regio- and stereochemistry is as shown. :Br: CH3 low [:Br] (CH3 + H-OH, :Br: excess H,0 (racemic)
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Draw the mechanism of the following reaction, using the curved-arrow notation to indicate the reorganization of electron density. Denote all intermediates, lone pairs, nonzero formal charges, countercharges, and reversibility or nonreversibility. Finally, explain concisely why a mixture of the stereoisomers 2 and 3 is obtained. 2 H-Br: `CH3 `CH3 :OH :Br: + `CH3 :Br: .. 3 + + H-OH, :Br:
do 8.32!

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