7. (4 pts.) The final product and the starting cyclohexanone are similar, and by

Question

7. (4 pts.) The final product and the starting cyclohexanone are similar, and by looking at the structures you may wonder how you would be able to tell that reaction actually occurred by comparing the infrared spectra of the cyclohexanone and the final product without looking at the fingerprint region. However, the infrared spectra are sufficiently different even above 1500 cm-1 that they can readily be distinguished. O: O: ON O: H+ cat. 2-acetylcyclohexanone cyclohexanone This is because of a perhaps unexpected structural feature of the final product, intramolecular hydrogen bonding. Draw a structure of the final product that illustrates this intramolecular hydrogen bonding and how it arises

Explanation / Answer

If the hydrogen bond is present between two atoms of the same molecule, then it is known as intramolecular hydrogen bonding.

This arises in the final product due to shifting of electron cloud within the molecule.

For example, the product is CH3C=OC6H9(=O), in linear form.

After intramolecular hydrogen bonding it will be CH3C-O=C6H9(=O).

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