Show how you might synthesize this compound from an alkyl bromide and a nucleophile in an SN2 reaction. CN 8 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Only draw the reactants. Separate multiple reactants using the sign from the drop-down menu. • If there is more than one possible combination of alkyl bromide and nucleophile, draw only one combination. • Do not include counter-ions, e.g., Na+, I, in your answer.

Show how you might synthesize this compound from an alkyl bromide and a nucleophile in an SN2 reaction. CN 8 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Only draw the reactants. Separate multiple reactants using the sign from the drop-down menu. • If there is more than one possible combination of alkyl bromide and nucleophile, draw only one combination. • Do not include counter-ions, e.g., Na+, I, in your answer.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter25: Enolate & Enol Nucleophiles

Section: Chapter Questions

Problem 11CTQ

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Consider this nucleophilic substitution reaction. 1. Highlight the electrophilic carbon in red, and highlight the leaving group in blue. Highlight the atom in the nucleophile that will attack the electrophilic center in green. Only atoms need to be highlighted and not the lone pairs or formal charges. 2. Draw the product(s) of the reaction. Include all lone pairs.
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A student wanted to know whether the greater proximity of the nucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl. Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?
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Rearrangements can occur during the dehydration of 1° alcohols eventhough no 1° carbocation is formed—that is, a 1,2-shift occurs as the C—OH2+ bond is broken, forming a more stable 2° or 3° carbocation, asshown in Equation [1]. Using this information, draw a stepwisemechanism for the reaction shown in Equation [2]. We will see anotherexample of this type of rearrangement
Fill in the missing reagents in the boxes below. some steps may require more than one step.
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