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Q8.5(ii):
Draw structures of the following derivatives. (ii) Cyclopropanone oxime

Solution :

Step 1: Structural Identification of the Parent Carbonyl

The parent molecule is cyclopropanone. Cyclopropanone consists of a three-membered carbon ring where one carbon atom is part of a carbonyl group ($C=O$).

  • Molecular Formula of Cyclopropanone: $C_3H_4O$.
  • Functional Group: Ketone moiety at the $C_1$ position of the cyclopropane ring.

Step 2: Mechanism of Oxime Formation

An oxime is formed via the nucleophilic addition-elimination reaction between a carbonyl compound and hydroxylamine ($NH_2OH$). [Per the Nucleophilic Addition Mechanism to Carbonyls].

The reaction proceeds as follows:

$\text{R}_2C=O + H_2N-OH \rightarrow \text{R}_2C=N-OH + H_2O$

In the case of cyclopropanone, the oxygen atom of the carbonyl is replaced by the $=N-OH$ (oxime) group while maintaining the cyclic structure.

Step 3: Geometrical Configuration

The oxime functional group exhibits $sp^2$ hybridization at the carbon atom. The nitrogen atom is double-bonded to the ring carbon and single-bonded to a hydroxyl group ($-OH$). The structure is planar at the imine bond.

Step 4: Structural Representation (SVG)

N OH Cyclopropane Ring

Step 5: Chemical Formula and Structural Summary

The structure consists of a cyclopropane ring substituted at the $1$-position with an $=N-OH$ group.

Component Description
IUPAC Name Cyclopropanone oxime
Chemical Formula $C_3H_5NO$
Hybridization (C=N) $sp^2$

Final Solution: The structure of cyclopropanone oxime is a three-membered cyclopropane ring containing a $C=N-OH$ functional group at the carbon formerly bonded to the carbonyl oxygen.


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