Question Details

Total number of possible isomers (both structural as well as stereoisomers) of cyclic ethers of molecular formula C4H8O is:

Options

A

6

B

8

C

10

D

11

Show Answer

Correct Answer :

Option C

10

10

Solution :

The correct option is 10.

To determine the total number of cyclic ether isomers for the molecular formula C4H8O (including both structural and stereoisomers), we can proceed step-by-step as follows:

Step 1: Calculate the Degree of Unsaturation (Double Bond Equivalent, DBE)
The formula for DBE is:

DBE=C+1-H2

For C4H8O:

DBE=4+1-82=1

Since the isomers must be cyclic ethers, the ring accounts for the 1 degree of unsaturation. Therefore, the molecules will contain a single ring with no double bonds.

Step 2: Classify by Ring Size
We can have cyclic ethers with 5-membered, 4-membered, and 3-membered rings containing oxygen.

1. 5-Membered Ring (Oxolane / Tetrahydrofuran ring)
A 5-membered ring consists of 4 carbon atoms and 1 oxygen atom.

  • Tetrahydrofuran (THF): There are no substituents, and no chiral centers. This gives 1 isomer.

2. 4-Membered Ring (Oxetane ring)
A 4-membered ring consists of 3 carbon atoms and 1 oxygen atom. The remaining 1 carbon atom is present as a methyl substituent.

  • 2-Methyloxetane: The methyl group is at carbon position 2. This carbon is chiral because it is bonded to -H, -CH3, -O-CH2-, and -CH2-CH2-. This gives a pair of enantiomers:
    • (R)-2-methyloxetane
    • (S)-2-methyloxetane
    This contributes 2 isomers.
  • 3-Methyloxetane: The methyl group is at carbon position 3. Carbon-3 is symmetric (not chiral). This contributes 1 isomer.
Total for 4-membered rings = 3 isomers.

3. 3-Membered Ring (Oxirane / Epoxide ring)
A 3-membered ring consists of 2 carbon atoms and 1 oxygen atom. The remaining 2 carbon atoms can be attached in two ways:

  • Case A: One ethyl substituent
    Ethyloxirane: The carbon attached to the ethyl group is chiral. This gives a pair of enantiomers:
      - (R)-ethyloxirane
      - (S)-ethyloxirane
    This contributes 2 isomers.
  • Case B: Two methyl substituents
    2,2-Dimethyloxirane: Both methyl groups are attached to the same ring carbon. There are no chiral centers. This contributes 1 isomer.
    2,3-Dimethyloxirane: Each ring carbon has one methyl group. Both ring carbons are chiral centers:
      - cis-2,3-dimethyloxirane (meso compound, optically inactive due to internal symmetry): 1 isomer.
      - trans-2,3-dimethyloxirane (chiral, exists as a pair of enantiomers, (2R,3R) and (2S,3S)): 2 isomers.
Total for 3-membered rings = 2 (ethyloxirane) + 1 (2,2-dimethyloxirane) + 3 (2,3-dimethyloxirane) = 6 isomers.

Step 3: Total Count
Adding up all the structural and stereoisomers:
Total=1 (5-membered)+3 (4-membered)+6 (3-membered)=10

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