Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 7, Problem 68P
When a single compound contains both a nucleophile and a leaving group, an intramolecular reaction may occur. With this in mind, draw the product of the following reaction.
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Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bond-making and bond-breaking processes.
Draw the two resonance structures of the enolate anion intermediate for this reaction.
In a Wittig reaction, a ketone or aldehyde reacts as an electrophile with a nucleophile called a Wittig reagent (or phosphonium ylide) to produce an alkene. The Wittig reagent is commonly synthesized first in a two-step process beginning with an alkyl halide, then reacted with the carbonyl compound. In this problem, you'll explore the mechanism of a multi-step synthesis to make an alkene using the Wittig approach.
Chapter 7 Solutions
Organic Chemistry (6th Edition)
Ch. 7.1 - Problem 7.1 Telfairine, a naturally occurring...Ch. 7.2 - Give the IUPAC name for each compound. a. b. c. d.Ch. 7.2 - Prob. 3PCh. 7.3 - An sp3 hybridized CCl bond is more polar than an...Ch. 7.4 - Prob. 5PCh. 7.6 - Prob. 6PCh. 7.7 - Prob. 10PCh. 7.8 - Prob. 15PCh. 7.8 - Prob. 16PCh. 7.8 - Prob. 17P
Ch. 7.11 - Prob. 18PCh. 7.11 - Prob. 19PCh. 7.11 - Draw the product of each SN2 reaction and indicate...Ch. 7.11 - Prob. 21PCh. 7.11 - Prob. 22PCh. 7.12 - What happens to the rate of an SN1 reaction under...Ch. 7.12 - Draw the products of each SN1 reaction and...Ch. 7.13 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7.15 - Problem 7.30 For each alkyl halide and...Ch. 7.15 - Prob. 30PCh. 7.15 - Prob. 31PCh. 7.15 - Prob. 32PCh. 7.15 - Prob. 33PCh. 7.15 - Prob. 34PCh. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - 7.53 Consider the following reaction.
Draw a...Ch. 7 - Prob. 57PCh. 7 - Prob. 58PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - 7.59 Pick the reactant or solvent in each part...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 62PCh. 7 - Prob. 63PCh. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 69PCh. 7 - Prob. 70PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 72PCh. 7 - Prob. 78P
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- The following molecule is an intermediate in the sythesis of strychnine, a poison commonly used as a rodenticide. The intermediate has a free alkoxide group, which serves as a nucleophile. Which site is electrophilic and in close enough proximity to be attacked by this nucleophile?arrow_forwardDetermine which would be more reactive with a nucleophilearrow_forwardIn a Michael addition, which carbon will the nucleophile add to? H₂C B syd A A B C Harrow_forward
- Which compound can act as a nucleophilearrow_forwardGive two possible [1,2]-rearrangement products where an alkyl group migrates in the following compound. Motivate also which of the two products will be formed preferentiallyarrow_forwardHeating an alcohol in the presence of sulfuric or phosphoric acid will cause a dehydration to occur: the removal of the elements of water from a molecule, forming an alkene. The reaction usually follows an E1 mechanism. The SN1 pathway is suppressed, both by heating the reaction mixture (more energy promotes the elimination pathway) and by using a strong acid whose conjugate base is a poor nucleophile. Draw curved arrow(s) to show how the alcohol reacts with phosphoric acid.arrow_forward
- In order to complete the synthesis shown below, you would need to use [ Select ] as the nucleophile source and [Select] as the solvent. H3C OH H3C Br H3CY CH3 H3C CH3arrow_forwardThe Wittig sequence includes this/these reaction step/s. O nucleophilic substitution of a phosphine on an alkyl halide O acid-base reaction removing a hydrogen from the carbon next to the phosphonium group to form an ylide O the aldehyde or ketone combines with the ylide to form an oxaphosphetane O the oxaphosphetane breaks down to form the alkene and a phosphine oxide O all of the above O none of the abovearrow_forwardThe following molecule undergoes an intramolecular reaction in the presence of pyrrolidinium acetate, the protonated form of pyrrolidine. Draw the product of this reaction, assuming that a dehydration reaction takes place.arrow_forward
- Explain why a methoxy group (CH3O) increases the rate of electrophilic aromatic substitution, but decreases the rate of nucleophilic aromatic substitution.arrow_forwardDraw the appropriate reagents and solvent above and or below the arrow necessary to conduct the following reactions.arrow_forwardSupply the structures of reactant(s) or product(s) for the following aldol and Claisen reactionsarrow_forward
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