An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the following sequence of reactions in which Q is an intermediate organic compound.
The structure of the compound Q is:
An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the following sequence of reactions in which Q is an intermediate organic compound.
The structure of the compound Q is:
The correct option is B
This is a reverse engineering problem. A fantastic clue is the number associated with the structure of acetone - 2. In other words, we have two molecules of acetone. This makes working backwards easy somewhat. The technical term used for “working backwards” or reverse engineering is called retrosynthetic analysis.
In the first step of the above reaction, dehydration happens. The dehydrated product, on ozonolysis yields two molecules of acetone. Observe the following retrosynthetic step:
The alkene is the product of dehydrating Q.
What are the possible structures of Q now? Also, the starting compound P and the final result - 2 molecules of acetone - retain the same number of carbons - 6!
Now think in terms what on dehydration would give the alkene shown above?
In this retrosynthetic analysis, the structure α - a tertiary alcohol - could not be the structure of Q. This is because Q is the product of NaBH4 reduction – a process that by itself, cannot yield a tertiary alcohol. Hence, Q is β.
This is a reverse engineering problem. A fantastic clue is the number associated with the structure of acetone - 2. In other words, we have two molecules of acetone. This makes working backwards easy somewhat. The technical term used for “working backwards” or reverse engineering is called retrosynthetic analysis.
In the first step of the above reaction, dehydration happens. The dehydrated product, on ozonolysis yields two molecules of acetone. Observe the following retrosynthetic step:
The alkene is the product of dehydrating Q.
What are the possible structures of Q now? Also, the starting compound P and the final result - 2 molecules of acetone - retain the same number of carbons - 6!
Now think in terms what on dehydration would give the alkene shown above?
In this retrosynthetic analysis, the structure α - a tertiary alcohol - could not be the structure of Q. This is because Q is the product of NaBH4 reduction – a process that by itself, cannot yield a tertiary alcohol. Hence, Q is β.
