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Exam 26: Orbitals and Organic Chemistry: Pericyclic Reactionse

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Question 21

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Classify the following reaction.

A) electrocyclic reaction
B) cycloaddition
C) sigmatropic rearrangement

D) A) and C)
E) A) and B)

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Question 22

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Exhibit 30-6 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 30-6. Explain the stereochemistry of product C.

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Step 2 is a thermal [1, 5] sig...

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Question 23

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Exhibit 30-2 Consider the reaction below to answer the following question(s): -Refer to Exhibit 30-2. Has this reaction taken place in a conrotatory manner or in a disrotatory manner?

Exhibit 30-7 Consider the Sommelet-Hauser rearrangement below to answer the following question(s): -Refer to Exhibit 30-7. Would you expect the Sommelet-Hauser rearrangement to be antarafacial or suprafacial? Explain.

Exhibit 30-6 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 30-6. Show how C is formed from B.

Under photochemical conditions, the following substance will undergo:

Define a pericyclic reaction.

Exhibit 30-7 Consider the Sommelet-Hauser rearrangement below to answer the following question(s) : -Refer to Exhibit 30-7. The Sommelet-Hauser rearrangement is an example of a [2, 3] sigmatropic rearrangement. How many pairs of electrons are involved in this reaction?

Exhibit 30-4 Consider the reaction below to answer the following question(s): -Refer to Exhibit 30-4. Explain the stereochemistry of this reaction.

Exhibit 30-6 Consider the reaction sequence below to answer the following question(s): -Refer to Exhibit 30-6. Explain the stereochemistry of product B.

Exhibit 30-6 Consider the reaction sequence below to answer the following question(s) : -Refer to Exhibit 30-6. Step 1 is an example of:

Classify the following reaction.

Exhibit 30-8 Classify each of the following sigmatropic reactions by order [x, y]. 26. ANSWER: [3, 3] POINTS: 1 27. ANSWER: [1, 7] POINTS: 1 28. ANSWER: [1, 5] POINTS: 1 Exhibit 30-9 Vitamin D₃, cholecalciferol, is synthesized under the skin by the photochemical pericyclic process shown below. Answer the following question(s) about these reactions. -Refer to Exhibit 30-9. The first step in this process is a(n) :

To answer the following question(s), consider the π molecular orbitals of a conjugated diene shown below: -Draw the product(s) you would expect to obtain from photochemical cyclization of (2Z, 4E)-hexadiene.

To answer the following question(s) , consider the π molecular orbitals of a conjugated diene shown below: -Refer to Exhibit 30-1. Which molecular orbital of a conjugated diene contains two nodes between nuclei?

Which of the following is not an electrocyclic reaction?

For an odd number of electron pairs (double bonds) , for cycloadditions reactions which of the following rules is correct?:

Exhibit 30-5 To answer the following question(s) , consider the reaction below: -Refer to Exhibit 30-5. What type of pericyclic reaction is involved in this transformation?

Exhibit 30-5 To answer the following question(s), consider the reaction below: -Refer to Exhibit 30-5. Propose a mechanism for the reaction that fully accounts for the formation of both products.

Exhibit 30-3 To answer the following question(s), consider the reaction below: -Refer to Exhibit 30-3. Two pericyclic reactions are involved in this synthesis of compound Y. Draw the structure of intermediate X and name it using IUPAC nomenclature.