The C-H bond in acetone, , has a of 19.2. Draw two resonance structures for its conjugate base.
Then, explain why acetone is much more acidic than propane, .
Acetone is more acidic than propane as its conjugate base is resonance stabilized.
The structures that depict the bonding/delocalization of electrons in a molecule are named resonance structures.
The higher the number of resonance structures of a molecule, the higher will be its stability.
The species obtained after removing or losing a proton from a molecule (acid) is its conjugate base.
The acid’s strength can be predicted by considering the stability of its conjugate base. The higher is the stability of the conjugate base, the greater is the strength of the acid.
The removal of a hydrogen atom from acetone generates its conjugate base.
The conjugate base of acetone has two resonance structures. The removal of a proton from propane yields its conjugate base (propyl anion).
The propyl anion has only one Lewis structure, and it does not participate in resonance.
The conjugate base of acetone is more resonance stabilized than that of propane. Thus, acetone is more acidic than propane.
Compounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes. In which form will amphetamine pass through a cell membrane?
Amino acids such as glycine are the building blocks of large molecules called proteins that give structure to muscle, tendon, hair, and nails.
a. Explain why glycine does not actually exist in the form with all atoms uncharged, but actually exists as a salt called a zwitterion.
b. What product is formed when glycine is treated with concentrated HCl?
c. What product is formed when glycine is treated with NaOH?
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