Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 11.6, Problem 9P
Starting with acetyl chloride, what neutral nucleophile would you use to make each of the following compounds?
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Which of the following could act as a nucleophile?
A) HCl
B) CH3NH2
C) BF3
D) CH3Br
Complete the following nucleophilic substitution reactions. In each reaction, show all electron pairs on both the nucleophile and the leaving group.
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
CH3
Chapter 11 Solutions
Essential Organic Chemistry, Global Edition
Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3PCh. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7PCh. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P
Ch. 11.7 - Prob. 11PCh. 11.8 - Prob. 13PCh. 11.8 - Using the mechanism for the acidcatalyzed...Ch. 11.8 - Prob. 15PCh. 11.8 - Prob. 16PCh. 11.8 - Prob. 17PCh. 11.9 - Prob. 18PCh. 11.10 - Show how each of the following esters could be...Ch. 11.11 - Which of the following reactions would lead to the...Ch. 11.12 - Prob. 22PCh. 11.12 - Prob. 23PCh. 11.13 - Prob. 24PCh. 11.13 - Prob. 25PCh. 11.14 - Prob. 26PCh. 11.14 - Prob. 27PCh. 11.14 - Prob. 28PCh. 11.15 - Prob. 29PCh. 11.15 - How would you synthesize the following compounds...Ch. 11 - Write a structure for each of the following a. N,N...Ch. 11 - Prob. 32PCh. 11 - Which ester is more reactive, methyl acetate or...Ch. 11 - What products would be formed from the reaction of...Ch. 11 - What products would be obtained from the following...Ch. 11 - Prob. 36PCh. 11 - a. Which compound would you expect to have a...Ch. 11 - a. List the following esters in order of...Ch. 11 - D. N. Kursanov, a Russian chemist, proved that the...Ch. 11 - Prob. 40PCh. 11 - Using an alcohol for one method and an alkyl...Ch. 11 - Prob. 42PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Show how the following compounds could be prepared...Ch. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53P
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- Consider the following groups of compounds. In each series circke the weaker (poorer) nucleophile. Please explain why.arrow_forwardWhat is the strongest nucleophile, NH3, CH4, CH3O-, or H2O?arrow_forwardThis reaction is an example of conjugate addition of a nucleophile to an a,ß-unsaturated carbonyl. CНз CHз Нао ОН Draw the two resonance structures of the enolate anion intermediate for this reaction.arrow_forward
- Supply the reagents that would be needed to perform the following reactions.arrow_forwardIn the reaction CH₂O + HCN CH₂CNOH, which species serves as a nucleophile?arrow_forwardThe compound below can be prepared with an alkyl iodide and a suitable nucleophile. Identify the alkyl iodide and the nucleophile that you would use. For an anionic nucleophile, you do not need to draw the counterion.arrow_forward
- Explain why a methoxy group (CH3O) increases the rate of electrophilic aromatic substitution, but decreases the rate of nucleophilic aromatic substitution.arrow_forwardThe compound below can be prepared with an alkyl iodide and a suitable nucleophile. Identify the alkyl iodide and the nucleophile that you would use. For an anionic nucleophile, you do not need to draw the counterion. Alkyl iodide: OH Draw Your Solution Nucleophile: Draw Your Solution SUPPORTarrow_forwardIn the following reactions; identify substrate, nucleophile and leaving grouparrow_forward
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