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1. a. tertiary amine
c. Some O functional groups involve an -OH group; these cannot possibly have the O heterocyclic, since O can only form two bonds. Similarly, groups with >C=O cannot have the O heterocyclic. Thus the only O groups that can have a heterocyclic O are those with the O attached to two C atoms. These include the ether, hemiacetal, acetal, ester and anhydride. If you are using the Ouellette book, all of these have been introduced by the time we get to amines.
d. Morphine has a phenol group, which has been replaced by an ether in codeine. Inspection of the structures shows -OH in morphine vs -OCH3 in codeine. [Calling the -OH group in the morphine an alcohol is not so good; simply calling it an -OH is evading the point. The -OCH3 in codeine is a methoxy group, but the general class is ether.]
e. The phenolic -OH is weakly acidic; the amino N is basic.
f. In acid, the N will be protonated, to produce the corresponding ammonium ion. In base, the phenol group will ionize, giving off H+ and leaving the phenolate ion.
2. a. The one on the right. Aliphatic amines are stronger bases than aromatic amines.
There are two key steps in answering this. First, you need to recognize that the amine on the left is an aromatic amine, and the one on the right is aliphatic. Second, you then realize that aliphatic amines are stronger bases than aromatic amines.
|b. The structures are shown at the right. Both the "common" chemical names and the biochemical names are given. Indeed, the vitamin niacin is related to nicotine, by the reaction described in this question. However, that is not how it is made biologically. The biosynthesis of niacin is from the amino acid tryptophan. (Niacinamide is part of the hydrogen-carrying cofactor NAD, nicotinamide adenine dinucleotide. See Metabolism chapter. Also, both niacin and NAD(H) are mentioned in passing by Ouellette; see index.)|
3. A 7-membered ring.
4. and 5.
The one stereocenter is marked with an * (just below it). This C, C#3 of the numbered chain, has four different groups: Cl, H (not shown explicitly), and two C-based units. One of the C-based units has one C, the other is large.
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Last update: August 16, 2011