3. Complete the following assigned problem from the textbook. [24 pts] hint: The addition of the first phenol to formaldehyde creates an intermediate that forms a resonance- stabilized cation. 16.65 Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = CH3), a reagent used to harden some plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways. R R H₂SO4 H₂O H H HO HO OH For full credit, bisphenol F • Use 'curly arrows' to denote electron flow. R=H Show all resonance forms of the intermediate cation described in the hint (above). Do not abbreviate structures. Show mechanisms for protonation and deprotonation steps.
3. Complete the following assigned problem from the textbook. [24 pts] hint: The addition of the first phenol to formaldehyde creates an intermediate that forms a resonance- stabilized cation. 16.65 Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = CH3), a reagent used to harden some plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways. R R H₂SO4 H₂O H H HO HO OH For full credit, bisphenol F • Use 'curly arrows' to denote electron flow. R=H Show all resonance forms of the intermediate cation described in the hint (above). Do not abbreviate structures. Show mechanisms for protonation and deprotonation steps.
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
Related questions
Question
![3. Complete the following assigned problem from the textbook. [24 pts]
hint: The addition of the first phenol to formaldehyde creates an intermediate that forms a resonance-
stabilized cation.
16.65 Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used
in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = CH3), a reagent used to harden some
plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways.
R R
H₂SO4
H₂O
H
H
HO
HO
OH
For full credit,
bisphenol F
•
Use 'curly arrows' to denote electron flow.
R=H
Show all resonance forms of the intermediate cation described in the hint (above).
Do not abbreviate structures.
Show mechanisms for protonation and deprotonation steps.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F39f6380b-55e3-47ff-8091-2f92e2b304db%2F2bf9aa4e-c4ea-405e-b49f-d9f69bad7e9a%2F1c89ktg_processed.jpeg&w=3840&q=75)
Transcribed Image Text:3. Complete the following assigned problem from the textbook. [24 pts]
hint: The addition of the first phenol to formaldehyde creates an intermediate that forms a resonance-
stabilized cation.
16.65 Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used
in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = CH3), a reagent used to harden some
plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways.
R R
H₂SO4
H₂O
H
H
HO
HO
OH
For full credit,
bisphenol F
•
Use 'curly arrows' to denote electron flow.
R=H
Show all resonance forms of the intermediate cation described in the hint (above).
Do not abbreviate structures.
Show mechanisms for protonation and deprotonation steps.
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 1 images
Recommended textbooks for you
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning