4. (a) Consider the reaction scheme below: OH Ph HO -OEt HO OEt HO Step 1 HO AcO- (i) Provide reagents for BOTH Step 1 and Step 3. (ii) Provide a curved arrow mechanism for Step 1. HO Step 2 Ph AcO- BnO Aco -OEt Step 3 OH Aco OEt
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.
![4.
(a) Consider the reaction scheme below:
OH
HO
-0
-OEt
HO
-OEt
HO
Step 1
HO
-0
ACO
ACO
(i) Provide reagents for BOTH Step 1 and Step 3.
(ii) Provide a curved arrow mechanism for Step 1.
(b) Provide a curved arrow mechanism for the following reaction and
explain the stereochemical outcome.
OH
BzO
Bz0
OBz
OBZ
Bz0
BZO SEt
HO
BZ0-
820
OMe
TIOH
CH₂Cl₂
4 A molecular sieves
BzO
Bz0
Step 2
BzO
Ph
0-
Aco
BnO
B20-
BZO
ACO
OH
-OEt
Step 3
Bzoome
-OEt](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fcd3095a6-c4b4-49ee-8698-92fdaab6a2f1%2F276afacf-ae7b-4d48-b7eb-94e141a52e70%2F5fke51_processed.jpeg&w=3840&q=75)
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