Because they are so often used as protecting groups in organic synthesis, the choice of which acetal to form metimes hinges upon how easily it can be removed by hydrolysis. This is because the longer it takes to protect and the harsher the necessary conditions, the more likely it is that unwanted side reactions will occur. eally an acetal protecting group should be easily formed and easily removed. For this reason, methylene etals like the one shown below are not ideal, as their rates of hydrolysis are quite slow. Acetonides, which u encountered in the practice problems, are often better choices. Fill in the boxes below with the expected drolysis products in each case. Then, using your knowledge from part (b) and clearly-drawn resonance uctures, briefly explain this observed difference in rates of hydrolysis. H30* H3C `CH3 (relatively slow) methylene acetal Hydrolysis Products H3C CH3 H3O* (relatively fast) H3C° CH3 acetonide Hydrolysis Products
Because they are so often used as protecting groups in organic synthesis, the choice of which acetal to form metimes hinges upon how easily it can be removed by hydrolysis. This is because the longer it takes to protect and the harsher the necessary conditions, the more likely it is that unwanted side reactions will occur. eally an acetal protecting group should be easily formed and easily removed. For this reason, methylene etals like the one shown below are not ideal, as their rates of hydrolysis are quite slow. Acetonides, which u encountered in the practice problems, are often better choices. Fill in the boxes below with the expected drolysis products in each case. Then, using your knowledge from part (b) and clearly-drawn resonance uctures, briefly explain this observed difference in rates of hydrolysis. H30* H3C `CH3 (relatively slow) methylene acetal Hydrolysis Products H3C CH3 H3O* (relatively fast) H3C° CH3 acetonide Hydrolysis Products
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
Question
please answer part c and d!
Transcribed Image Text:d. Because they are so often used as protecting groups in organic synthesis, the choice of which acetal to form
sometimes hinges upon how easily it can be removed by hydrolysis. This is because the longer it takes to
deprotect and the harsher the necessary conditions, the more likely it is that unwanted side reactions will occur.
Ideally an acetal protecting group should be easily formed and easily removed. For this reason, methylene
acetals like the one shown below are not ideal, as their rates of hydrolysis are quite slow. Acetonides, which
you encountered in the practice problems, are often better choices. Fill in the boxes below with the expected
hydrolysis products in each case. Then, using your knowledge from part (b) and clearly-drawn resonance
structures, briefly explain this observed difference in rates of hydrolysis.
H30*
H3C
(relatively
slow)
`CH3
methylene
acetal
Hydrolysis Products
H3C CH3
H30*
H;C
(relatively
fast)
`CH3
acetonide
Hydrolysis Products
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