5. Explain why 1-phenylpropan-2-ol undergoes skeletal rearrangement when treated with concentrated hydrochloric acid to yield (1-chloropropyl)benzene. CI conc. HCI ÕH 1-phenylpropan-2-ol (1-chloropropyl)benzene Note: it might be confusing that this molecule undergoes rearrangement because both carbon's 1 and 2 of the propane chain have secondary substitution. Problem solving tip: start by drawing the complete curved-arrow mechanism for this transformation (SN1 with a skeletal rearrangement!). Then, consider the relative energies of the two secondary carbocations in the mechanism.
5. Explain why 1-phenylpropan-2-ol undergoes skeletal rearrangement when treated with concentrated hydrochloric acid to yield (1-chloropropyl)benzene. CI conc. HCI ÕH 1-phenylpropan-2-ol (1-chloropropyl)benzene Note: it might be confusing that this molecule undergoes rearrangement because both carbon's 1 and 2 of the propane chain have secondary substitution. Problem solving tip: start by drawing the complete curved-arrow mechanism for this transformation (SN1 with a skeletal rearrangement!). Then, consider the relative energies of the two secondary carbocations in the mechanism.
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
Hello I’m having hard understanding it’s mechanism and it’s skeletal rearrangements. Can you help explain the conjugation and relative energies of species involved?
Transcribed Image Text:2B,kclass 3-problems, MO conjugated pi systems.pdf (196 KB)
base stability (recall Organic Chemistry 1).
5. Explain why 1-phenylpropan-2-ol undergoes skeletal rearrangement when treated with
concentrated hydrochloric acid to yield (1-chloropropyl)benzene.
CI
conc. HCI
1-phenylpropan-2-ol
(1-chloropropyl)benzene
Note: it might be confusing that this molecule undergoes rearrangement because both carbon's 1 and
2 of the propane chain have secondary substitution.
Problem solviņng tip: start by drawing the complete curved-arrow mechanism for this transformation
(SN1 with a skeletal rearrangement!). Then, consider the relative energies of the two secondary
carbocations in the mechanism.
W
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