Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 11, Problem 38P
- a. List the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate).
- b. List the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).
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What is the major difference between the base-catalyzed and acid-catalyzed processes for nucleophilic addition of water to aldehydes and ketones?
a. The base-catalyzed reaction takes place rapidly because hydroxide ion is a much better nucleophile than neutral water.
b. The rate of reaction in base catalyzed process is slower than acid catalyzed process.
c. The acid-catalyzed reaction takes place rapidly because the protonated carbonyl compound is a much better electrophile than the neutral compound.
d. Only 1 and 3 are correct.
Identify the sequence of curved arrows (electron movement) in the steps of the following two separate reactions. a. proton transfer, proton transferb. proton transfer, loss of a leaving groupc. proton transfer, nucleophilic attackd. nucleophilic attack, proton transfer
a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of thetetrahedral intermediate):
b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of thetetrahedralintermediate).
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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- Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating a. similarities. b. differences. 1. acid-catalyzed formation of a hydrate 2. acid-catalyzed conversion of an aldehyde to a hemiacetal 3. acid-catalyzed conversion of a hemiacetal to an acetal 4. acid-catalyzed hydrolysis of an amidearrow_forward1) The first mechanistic step of an acid catalyzed nucleophilic addition to a polar pi bond when the nucleophile is weak is which of the following? a. A nucleophile addition b. A proton transfer to the nucleophile c. A proton transfer from the nucleophile d. A proton transfer to the carbonyl e. A proton transfer from the carbonylarrow_forward6. Circle the structure with the most nucleophilic double bond. Put a box around the structure with the least nucleophilic double bond. OHarrow_forward
- 1. For the following reaction step, indicate which pattern of arrow pushing it represents. a. proton transferb. rearrangementc. loss of a leaving group2. Melphalan, a drug used in chemotherapy, reacts with itself in the body before binding with its target, as illustrated in the mechanism below. What is the first pattern of arrow pushing seen in this reaction? a. rearrangementb. loss of a leaving groupc. nucleophilic attackarrow_forwardIndicate who acts as nucleophile and electrophile in the reaction and draw the hemiacetal product.arrow_forwardFor each reaction, write the letter corresponding to the type of reaction (before the number) and draw the MAJOR product (in the product side). A. Nucleophilic Addition B. Nucleophilic Condensation C. Nucleophilic Acyl Substitutionarrow_forward
- Specify the reaction conditions to favour the indicated elimination mechanism. a. Strong base, such as hydroxide, an alkoxide, or equivalent b. Water or alcohol or equivalent weak base with heat c. Weak acid, such as formic acid, or equivalent d. Strong base, such as hydroxide, an alkoxide, or equivalentarrow_forward1. Attack the alkyl chloride with the stronger nucleophile. 2. Deprotonated to form the productarrow_forwardexplain why carbonyl compounds are so attractive to both nucleophiles and electrophilesarrow_forward
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