Question

Many drugs are sold as their hydrochloride salts (R$_2$NH$_2{^+}$ Cl$^-$), formed by reaction of an amine (R$_2$NH) with HCI. a. Draw the product (a hydrochloride salt) formed by reaction of acebutolol with HCI. Acebutolol is a $\beta$ blocker used to treat high blood pressure. b. Discuss the solubility of acebutolol and its hydrochloride salt in water. c. Offer a reason as to why the drug is marketed as a hydrochloride salt rather than a neutral amine.

Name: Problem 48, Chapter 3: Organic Chemistry
Uploaded: 2019-03-24T01:20:26-08:00
Duration: 1 min 50 s
Channel: Chloe Schroeder

   Many drugs are sold as their hydrochloride salts (R$_2$NH$_2{^+}$ Cl$^-$), formed by reaction of an amine (R$_2$NH) with HCI.
a. Draw the product (a hydrochloride salt) formed by reaction of acebutolol with HCI. Acebutolol is 
a $\beta$ blocker used to treat
high blood pressure.
b. Discuss the solubility of acebutolol and its hydrochloride salt in water.
c. Offer a reason as to why the drug is marketed as a hydrochloride salt rather than a neutral amine.

Organic Chemistry

Janice Gorzynski… 4th Edition

Chapter 3, Problem 48

Instant Answer

Solved by Expert Chloe Schroeder

03/24/2019

Step 1

The most basic site on acebutolol is the lone pair of electrons on the oxygen atom. This site will attack the hydrogen in HCl, forming a protonated compound. The structure of this compound can be represented as follows: R$_2$NH$_2{^+}$ Cl$^-$ where R represents Show more…

Show all steps

Thanks for your feedback!

Many drugs are sold as their hydrochloride salts (R$_2$NH$_2{^+}$ Cl$^-$), formed by reaction of an amine (R$_2$NH) with HCI. a. Draw the product (a hydrochloride salt) formed by reaction of acebutolol with HCI. Acebutolol is a $\beta$ blocker used to treat high blood pressure. b. Discuss the solubility of acebutolol and its hydrochloride salt in water. c. Offer a reason as to why the drug is marketed as a hydrochloride salt rather than a neutral amine.