Novocain, a local anesthetic, is the ammonium salt of procaine.
a. Draw the condensed structural formula for the ammonium salt (procaine hydrochloride) formed when procaine reacts with HCl. (Hint: The tertiary amine reacts with HCl.)

Question

Novocain, a local anesthetic, is the ammonium salt of procaine.

Condensed structural formula of procaine, a local anesthetic, showing its chemical structure.

a. Draw the condensed structural formula for the ammonium salt (procaine hydrochloride) formed when procaine reacts with HCl. (Hint: The tertiary amine reacts with HCl.)

Accepted Answer

Welcome back everyone. Benzocaine, a topical anesthetic reacts with hydrochloric acid to form its hydrochloride salt. It contains an ester group and the primary amino group through the condensed formula for benzocaine hydrochloride, hint the nitrogen atom reacts with HCL. Now, if we're interested in the condensed formula, we want to recall that this is generally a one line formula which only involves text. But the problem here is that we have a six member ring. And if we try to use a text formula, we will distort the identity of the compound and we will not be able to recreate it, right. So essentially what we want to do whenever there is benzene is simply draw out the benzene ring itself, not changing the positions of those substituents write and only use the rules for condensed formulas for the side chains. Otherwise, if we were to write C six H four, for example, we would not be able to tell where the substituents are. So first of all, we are going to take the ester group and turn it into a condensed formula because as we understand, according to the hand, it's the nitrogen atom that reacts with HCL which means that the ester group is unaffected. So we are going to take those atoms as we can see, we have carbon, which is implicit double bonded to oxygen, single bonded to oxygen. And then we have c another c and of course, if we have two bonds, there must be two hydrogen atoms. If we have one bond, there must be three implicit hydrogens. And now we can simply combine those into coo ch two ch three. So we just list all of those elements in sequence, see 00 C two C three. As you can see, we're not adding any bonds, we're just listing all of those elements in sequence. And now let's focus on the amino group. I mean, a group essentially reacts with HCL. Now, what does that mean? Well, Ngen has a long pair of electrons and we are observing an acid base reaction. So nitrogen is capable of accepting the acidic hydrogen from HCL. And it simply becomes NH three with a positive charge on nitrogen, right? And essentially what we're going to do is draw square brackets because we are going to observe an ionic compound. And knowing that nitrogen has a formal positive charge, we either add it to nitrogen to make it really, really explicit or we can add that positive charge outside of the square brackets. And now the counter ion is the chloride anion cl with a negative charge. And that's how we get our structure in order not to have a duplicate charge, we can simply remove that positive charge from nitrogen. We can clearly see that the only element that can have a positive charge in the structure is nitrogen itself, right? So we have got the representation off Benzo came hydrochloride salt. Thank you for watching.

Novocain, a local anesthetic, is the ammonium salt of procaine.

a. Draw the condensed structural formula for the ammonium salt (procaine hydrochloride) formed when procaine reacts with HCl. (Hint: The tertiary amine reacts with HCl.)

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Key Concepts

Ammonium Salts

Condensed Structural Formula

Tertiary Amines