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Correct answer: 5
The user wants to find the total number of cyclic isomers for a hydrocarbon with the molecular formula .
Step 1: Calculate the Degree of Unsaturation (DBE)
The degree of unsaturation (also known as the double bond equivalent) for a hydrocarbon with the formula is calculated using the formula: For , we have and . A DBE of 2 implies that the molecule can have one of the following combinations:
- Two double bonds
- One triple bond
- Two rings
- One ring and one double bond
Since the question asks for cyclic isomers, we only need to consider structures that contain at least one ring. This leaves two possibilities:
- One ring and one double bond.
- Two rings (bicyclic compounds).
Step 2: Enumerate Isomers with One Ring and One Double Bond
We consider different ring sizes for the carbon skeleton.
Case 2a: Four-membered ring
- If the skeleton is a four-membered ring (a cyclobutane derivative), we need to introduce one double bond to satisfy the formula . The parent saturated ring is cyclobutane ().
- Placing a double bond inside the ring gives cyclobutene. Due to the symmetry of the ring, there is only one possible position for the double bond.
Isomer 1: Cyclobutene
Case 2b: Three-membered ring
- If the skeleton is a three-membered ring (a cyclopropane derivative), one carbon atom must be a substituent (a methyl group). The parent structure is methylcyclopropane ().
- We need to introduce one double bond to get to the formula .
- The double bond is inside the ring (endocyclic): The cyclopropene ring has two sp² hybridized carbons and one sp³ hybridized carbon. The methyl group can be attached to either type.
- If the methyl group is on one of the double-bonded carbons, we get 1-methylcyclopropene.
- If the methyl group is on the non-double-bonded carbon, we get 3-methylcyclopropene.
- The double bond is outside the ring (exocyclic): The double bond can be formed between the ring and the substituent carbon. This gives a methylidene group () attached to a cyclopropane ring, which is methylidenecyclopropane.
So, from the three-membered ring skeleton, we get three isomers: Isomer 2: 1-Methylcyclopropene Isomer 3: 3-Methylcyclopropene Isomer 4: Methylidenecyclopropane
Step 3: Enumerate Isomers with Two Rings
- These are bicyclic compounds. With four carbon atoms, we are looking for bicyclobutane isomers.
- A possible structure is formed by fusing two three-membered rings along a common C-C bond. This results in a structure with two bridgehead carbons and two bridges of length 1, and a zero-length bridge (direct bond between bridgeheads).
- This structure is called bicyclo[1.1.0]butane. Let's check its formula. It has 4 carbons. The two bridgehead carbons are each bonded to 3 other carbons, so they each have one hydrogen. The other two carbons are each bonded to 2 carbons, so they each have two hydrogens. Total hydrogens = . The formula is , which is correct.
- No other bicyclic or spirocyclic structures are possible for .
Isomer 5: Bicyclo[1.1.0]butane
Step 4: Final Count
By systematically analyzing all possibilities, we have found the following 5 unique cyclic structural isomers:
- Cyclobutene
- 1-Methylcyclopropene
- 3-Methylcyclopropene
- Methylidenecyclopropane
- Bicyclo[1.1.0]butane
Note: The question asks for the total number of cyclic isomers. This can sometimes include stereoisomers. In this set, 3-methylcyclopropene is chiral and exists as a pair of enantiomers. If stereoisomers were included, the total count would be 6. However, for integer-type questions in JEE, it is common to ask for the number of structural isomers unless specified otherwise. Since 5 is the number of structural isomers and it matches the provided answer, this is the intended interpretation.
The total number of cyclic isomers is 5.
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