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    19 Aldehydes and Ketones

    Methandrostenalone

    In this chapter, we begin to study the reactions of functional groups that contain a carbonyl group
    (C=O). Functional groups that contain a carbonyl group include aldehydes, ketones, carboxylic
    acids and their derivatives, and many classes of cellular molecules. These compounds have some
    common chemistry, but there are many variations. We will consider the reactions of carboxylic acids
    and their derivatives in greater detail in Chapters 20–23.

    19.1 A carbonyl group consists of a double bond linking a carbonyl carbon atom and a carbonyl oxygen
    THE CARBONYL GROUP atom. The carbonyl oxygen atom shares two of its six valence electrons with the carbonyl carbon atom.
    Its remaining four valence electrons remain as two sets of electron lone pairs. The carbonyl carbon
    atom shares two of its four valence electrons with the carbonyl oxygen atom, and its remaining two
    electrons form two single bonds to other atoms. Formaldehyde (CH₂O) is the simplest compound
    with a carbonyl group.
    H
    C O C O
    H
    formaldehyde

    The carbonyl carbon atom, which is sp2-hybridized, contributes one electron to each of the three
    hybrid orbitals, forming three s bonds. Formaldehyde has two s bonds with hydrogen atoms and
    one s bond with the carbonyl oxygen atom. These coplanar bonds lie at approximately 120° to each
    other. The fourth electron of the carbonyl carbon atom occupies a 2p orbital perpendicular to the
    plane of the three sp2-hybrid orbitals. The carbonyl oxygen atom, also sp2-hybridized, contributes
    one of its six valence electrons to the sp2-hybrid orbital that forms a s bond with the carbonyl car-
    bon atom. Four valence electrons remain as two sets of nonbonded electron pairs in the other two
    sp2-hybrid orbitals. They lie in the same plane approximately 120° to each other and to the carbon–
    oxygen bond (Figure 19.1). The last valence electron occupies a 2p orbital perpendicular to the plane
    of the sp2-hybrid orbitals. The 2p orbitals of the carbon and oxygen atoms overlap to form a π bond.
    The three atoms or groups of atoms bonded to the carbonyl carbon of an aldehyde or a
    ketone are not equivalent, but the bond angles around the carbonyl carbon atom in aldehydes and
    ketones come close to the idealized 120° bond angles of an sp2-hybridized carbon atom, as shown
    for formaldehyde and acetone.

    121.7o 121.4o
    H CH3
    116.5o C O 117.2o C O
    H CH3
    formaldehyde acetone

    Organic Chemistry. https://doi.org/10.1016/B978-0-12-812838-1.50019-0 Copyright © 2018 Elsevier Inc. All rights reserved. 561

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