Bonds Functional Groups

Question 1

Van der Waals important for

Answer 1

Hydrocarbons, lipophiic/hydrophobic molecule

Question 2

Common metabolism of alkene

Answer 2

Epoxidation catalyzed by P450

Question 3

Common metabolism of Alkane

Answer 3

Mostly non-reactive, but w-hydroxylation by cytochrome P450 (CYP) could occur

Question 4

Common metabolism of aromatic hydrocarbon

Answer 4

Aromatic Hydroxylation

Question 5

There is a permanent dipole between C-X, but dipole-dipole interaction is weak except for

Answer 5

C-F

Question 6

In general, van der waals is more important for

Answer 6

halogneated hydrocarbons and increases with larger halogen

Question 7

Periodic size trend

Answer 7

Bottom left is biggest size

Question 8

Aliphatic alcohol

Answer 8

Neutral under physiological conditions: non-ionizable

Question 9

Phenol

Answer 9

Much more acidic OH group, but still neutral at pH = 7.4…. Hydrogen bonding acceptor and donor

Question 10

Hydrogen bond donor and acceptor

Answer 10

Question 11

Keto-enol tautomerism

Answer 11

Question 12

Hemiacetal hemiketal

Answer 12

Question 14

Amines

Answer 14

Question 15

Why are aryl amines not very basic?

Answer 15

Aryl amines are not very basic due to aromatic delocalization of lone-pair electrons

Question 16

Quarternary Ammonium Salts

Answer 16

Permanently postively charged

Not an acid or base

Does not participate in acid or base reactions

Question 17

Carboxylic Acids

Answer 17

Easily ionizable at pH = 7.4

Multiple sites of Hydrogen bonding (increased water solub)

ion-dipole interaction for the ionized form (Increased water solub)

Question 19

Ester

Answer 19

H-bond acceptor

Hydrolyzed easily

Esters are often prodrugs

Question 20

Amide

Answer 20

Does not hydrolyze easily

h-Bond donor

High water solub

Amide is neutral as N is not basic (resonance spreads lone-pair electrons)

Question 21

Carbonates, Carbamates, Urea

Answer 21

Question 22

Amidines and guanidines

Answer 22

Question 23

Sulfonic acids and sulfonamides

Answer 23

Question 24

Nitrate Nitrite

Answer 24

Question 25

Oxime and Hydrazone/hydrazine/hydrazide

Answer 25

Question 26

5 and 6 member rings. Which ones are basic

Answer 26