Author: Anonymous

Part1: Consider the structure of the drug NICOTINE and the pKa table shown here.  Drug HA BH+ Nicotine  — N1=3.12 N2=8.02 *** a) Explain the differences in pKa values for N1 and N2. [blank1] (e.g., the pKa for N1 is greater/less than pKa for N2 because…) *** b) At what pH would nicotine be sufficiently protonated to have a total +2 charge? [blank2] (e.g. pH = ##) Part 2: Nicotine (in nicotine gum) is sometimes flavored with artificial sweeteners such as acesulfame, an acidic compound shown here: *** c) The acidic group in acesulfame is a sulfonamide. Which point(s) on the molecule (a-f) include the sulfonamide functional group? [blank3] (e.g. a to b; b to f; a-c; etc…) *** d) Assuming nicotine is completely ionized (+2, see b above)…If nicotine and acesulfame reacted to form a salt, what would be the ratio of nicotine to acesulfame? [blank4] (e.g. 2:3 or 2 to 3) Considering either functional group N1 or N2 in nicotine, use the Henderson-Hasselbalch equation to determine the molar ratio and % IONIZED, %UNIONIZED for Nicotine at pH 7.4  Possibly helpful equations:   pH = pKa + log(A-)/(HA)    -or-     pH = pKa + log(B)/(BH+) *** e) Please specify N1 or N2 and then your percentages: [blank5] (e.g. N1: %I = ##.#; %UI = ##.#)

The following statements are ALL FALSE. CORRECT THE STATEMENTS *** Alkaloids like quinine are biologically active amine-containing compounds typically found in animals [blank1] *** The DNA/RNA base shown here is categorized as a pyrimidine [blank2]

Consider the drugs PB and AU shown here. Which compound(s) is/are susceptible to ester hydrolysis? Select all that apply…

Consider the drugs PB and AU shown here. Which drug could form a salt by reacting with NaCl?

The drugs cephalosporin, cefipime, and ceftriaxone all contain a beta-lactam pharmacophore; therefore the are likely to exhibit similar biological and/or pharmacological activity.

Consider the compound Elamipretide shown here. ENTER A, B, C, D, E or NONE to complete the blanks… *** a) Identify a region that is considered POLAR [blank1] *** b) Identify a region that is considered lipophilic [blank2] *** c) Identify a region that includes that amino acid Phenylalanine [blank3] *** d) Identify a region that can ionize greater than 50% at pH 7.4 [blank4] *** e) What types of bonds present in Elamipretide would readily hydrolyze under acidic conditions? Briefly explain… [blank5]

Consider the compound Efegatron shown here. ENTER A, B, C, D, or NONE to complete the blanks… *** a) Identify a region that is considered NONPOLAR [blank1] *** b) Identify a region that is considered hydrophilic [blank2] *** c) Identify a region that includes that amino acid Glutamic acid [blank3] *** d) Identify a region that can ionize greater than 50% at pH 7.4 [blank4] *** e) What types of bonds present in Efegatron would readily hydrolyze under acidic conditions? Briefly explain… [blank5]  

Ascorbic acid (Vitamin C) has two pKas, see figure below *** Which is the stronger acid? [blank1] *** Briefly explain your answer… [blank2]  

Consider the panel of amines.  – Select the amine group that is least likely to behave as a hydrogen bond acceptor.

Question 11 (24 points). Provided below is the structure of (+)-xylose. Non-bonding electrons have been omitted for clarity. Re-draw the structure of (+)-xylose on paper.  To preview the image: Click HERE Identify ALL of the chiral/asymmetric centers in (+)-xylose and indicate them with a * symbol. Assign the absolute configuration for each chiral/asymmetric center in (+)-xylose. Draw the structure of (-)-xylose and assign the configuration for each chiral/asymmetric center in (-)-xylose.