2. There are two types of mechanisms for epoxide openings. Use the examples below to: Describe the two pathways for epoxide opening (when do they usually occur? What should you look for? Etc.) a. Explain why two different products are formed in these two examples. Include mechanisms for both reactions. b. Pathway 1: Pathway 2: HCI OCH3 NaOCH3 OH HO H3CO CH3OH CH3OH

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.42P
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Can you help me understand the two pathways for epoxide and its mechanism?

2.
There are two types of mechanisms for epoxide openings. Use the examples below to:
Describe the two pathways for epoxide opening (when do they usually
occur? What should you look for? Etc.)
Explain why two different products are formed in these two examples.
Include mechanisms for both reactions.
a.
b.
Pathway 1:
Pathway 2:
HCI
LOCH3
NaOCH3
HO
H3CO
HO
CH3OH
CH3OH
CHON
Transcribed Image Text:2. There are two types of mechanisms for epoxide openings. Use the examples below to: Describe the two pathways for epoxide opening (when do they usually occur? What should you look for? Etc.) Explain why two different products are formed in these two examples. Include mechanisms for both reactions. a. b. Pathway 1: Pathway 2: HCI LOCH3 NaOCH3 HO H3CO HO CH3OH CH3OH CHON
Expert Solution
Step 1 Analysis

Given: Reactions 

To find: The mechanism of the above reactions and give out a reason why the products formed are different. 

Solution: Epoxide is a cyclic ether. In both the Reactions opening of epoxide ring takes place . 

In the above reaction if the Epoxide ring opening takes place in presence of strong acid then the attack takes place from backward side and the group which is on dash will go on wedge. 

But if the Epoxide ring opening takes place in presence of base than the attack takes place from same side and the group which is on dash will remain on dash or which remain on wedge will remain on wedge only.

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