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11 / proble
Problem
Compound X is optically inactive and has the formula C16H16Br2. On treatment with strong base,
X gives hydrocarbon Y, C16H14. Compound Y absorbs 2 equivalents of hydrogen when reduced
over a palladium catalyst and reacts with ozone to give two fragments. One fragment, Z, is an
aldehyde with formula C7H6O. The other fragment is glyoxal, (CHO)2. Write the reactions
involved, and suggest structures for X, Z, and Z. What is the stereochemistry of X?
Step-by-step solution
Step 1 of 7
Compound X is:
Comment
Step 2 of 7
Compound Y is:
Comment
Step 3 of 7
Compound Z is:
Comment
Step 4 of 7
Reactions:
(1)
Comment
Step 5 of 7
(2)
Comment
Comment
Step 7 of 7
Stereochemistry of compound X:
In this compound ‘X’ two chiral centers are present but this compound is optically inactive due to
plane of symmetry (meso-compound).
Comment