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CHY412: Advanced Organic Chemistry

Instructor: Dr. Basudev Sahoo (SoC, IISER TVM)


Problem Set-2

Problem-1: Write the structures of the product A, B and C with proper


stereochemistry. Write the mechanism for the product B and C formation.

[Hint: Class note; Enders Tetrahedron 2002, 58, 2253]


Problem-2: Write the structures of the product A, B and C with proper
stereochemistry. Write the mechanism for the product B and C formation.

[Hint: Enders Tetrahedron 2002, 58, 2253]


Problem-3: Select the suitable hydrazine-based auxiliary for (R)-Lilial synthesis. Write
the structures of the product A and C with proper stereochemistry. Write the
mechanism for the 2nd and 3rd steps.

[Hint: Enders Tetrahedron 2002, 58, 2253]


Problem-4: Write the structures of the product A and B with proper stereochemistry.
Write the mechanism for the product A formation.

[Hint: Class note]


Problem-5: Write the structures of the product A and B with proper stereochemistry.
Write the mechanism for the product A and B formation.

[Hint: Class note; Organic Chemistry Book - Clayden]


CHY412: Advanced Organic Chemistry
Instructor: Dr. Basudev Sahoo (SoC, IISER TVM)
Problem Set-2

Problem-6: Write the structures of the product A and B with proper stereochemistry.
Write the mechanism for the product A formation.

[Hint: Class note for similar DA reaction; Organic Chemistry Book - Clayden]
Problem-7: Write the structures of the compound A and B with proper stereochemistry
and explain the origin of stereoselectivity.

[Hint: Class note for similar alkylation reaction; Organic Chemistry Book - Clayden]
Problem-8: Write the structures of the product I with proper stereochemistry and
explain the origin of stereoselectivity.

[Hint: Class note; Oppolzer, Pure & Appl. Chem. 1990, 62, 1241]
Problem-9: Write the structures of the product A with proper stereochemistry and
explain the origin of stereoselectivity.

[Hint: Class note]


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