30. There is another approach to predicting the stereochemistry of electrocyclic ring closures. One simply looks at the ends of the HOMO to conclude the proper direction for rotation of the bond by creating in-phase interactions during closure. Show that this method also predicts conrotatory closure for butadiene and disrotatory closure for hexatriene. 31. Predict the thermally allowed products of the following two mraction

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...
icon
Related questions
icon
Concept explainers
Question
30. There is another approach to predicting the stereochemistry of electrocyclic ring closures. One simply looks at the ends
of the HOMO to conclude the proper direction for rotation of the bond by creating in-phase interactions during closure.
Show that this method also predicts conrotatory closure for butadiene and disrotatory closure for hexatriene.
31. Predict the thermally allowed products of the following two reactions.
2 D
O
32. The following reaction is known as the Carroll rearrangement. Write a mechanism for this reaction. What pericyclic
reactions involved?
RR
H
Base
Heal
O
33. At first glance, the following reaction appears to be a [2 + 2] cycloaddition of a single double bond from cyclopentadiene
with the C=C double bond of diphenylketene. However, it has been experimentally shown that the product actually
results from two more conventional pericyclic reactions. Show by writing an alternative mechanism what these two
reactions must be.
I
Ph
Ph
Ph
Ph-
CO₂
O
34. The retroene reaction is, as the name implies, the reverse of an ene reaction. Show how the following reaction conforms to
this name. Explain the cis stereochemistry in the product.
A
35. A rare, but sometimes observed, class of pericyclic reactions is called atom transfer or group transfer reactions. A single
example is given below, where two hydrogens are transferred to an alkene in a concerted single-step reaction. Using ethyl-
ene and ethane as models for the alkene and alkane portion of this reaction, draw an orbital correlation diagram for this
reaction. Is it allowed or forbidden? Similarly, analyze the reaction using an FMO approach, and lastly examine aromatic
transition state theory and the generalized pericyclic selection rule.
Ring-opening
36. Figure 15.9 defined suprafacial and antarafacial interactions of a lone pair in ap orbital (called an o component).
Using these definitions, predict if the ring-opening of the cyclopropyl anion shown below will occur in a conrotatory
or disrotatory fashion. What will be the stereochemistry of the product?
arrow pushing shows a cvelic
Transcribed Image Text:30. There is another approach to predicting the stereochemistry of electrocyclic ring closures. One simply looks at the ends of the HOMO to conclude the proper direction for rotation of the bond by creating in-phase interactions during closure. Show that this method also predicts conrotatory closure for butadiene and disrotatory closure for hexatriene. 31. Predict the thermally allowed products of the following two reactions. 2 D O 32. The following reaction is known as the Carroll rearrangement. Write a mechanism for this reaction. What pericyclic reactions involved? RR H Base Heal O 33. At first glance, the following reaction appears to be a [2 + 2] cycloaddition of a single double bond from cyclopentadiene with the C=C double bond of diphenylketene. However, it has been experimentally shown that the product actually results from two more conventional pericyclic reactions. Show by writing an alternative mechanism what these two reactions must be. I Ph Ph Ph Ph- CO₂ O 34. The retroene reaction is, as the name implies, the reverse of an ene reaction. Show how the following reaction conforms to this name. Explain the cis stereochemistry in the product. A 35. A rare, but sometimes observed, class of pericyclic reactions is called atom transfer or group transfer reactions. A single example is given below, where two hydrogens are transferred to an alkene in a concerted single-step reaction. Using ethyl- ene and ethane as models for the alkene and alkane portion of this reaction, draw an orbital correlation diagram for this reaction. Is it allowed or forbidden? Similarly, analyze the reaction using an FMO approach, and lastly examine aromatic transition state theory and the generalized pericyclic selection rule. Ring-opening 36. Figure 15.9 defined suprafacial and antarafacial interactions of a lone pair in ap orbital (called an o component). Using these definitions, predict if the ring-opening of the cyclopropyl anion shown below will occur in a conrotatory or disrotatory fashion. What will be the stereochemistry of the product? arrow pushing shows a cvelic
Expert Solution
steps

Step by step

Solved in 5 steps with 5 images

Blurred answer
Knowledge Booster
IR Spectroscopy of Organic Molecules
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Pushing Electrons
Pushing Electrons
Chemistry
ISBN:
9781133951889
Author:
Weeks, Daniel P.
Publisher:
Cengage Learning