Organic chemistry Lecture

Question 1

Define functional groups

Answer 1

Key components of a drug that allow the drug molecule to be a drug
Ones that can be interconverted to something else

Question 2

What do FGs control?

Answer 2

Critical properties: solubility, route of administration, binding (potency), mode of action, metabolism, duration and adverse effects

Question 3

What is the electronic effects of FGs?

Answer 3

Measured by its ability to either donate electrons to a neighbor or pull electrons away from its neighbor

Question 4

Define resonance

Answer 4

occurs when electrons are shared between a group of atoms that have adjacent double bonds and lone pairs of electrons

Question 5

Define inductive effects

Answer 5

Depends on the overall electonegativity of an atom
Defines how easily an atom or functional group can attract electrons from another atom or FG and onto itself
Measures how easily the atom can hold a negative charge
—-> Creates an unequal distribution of charge and results in a dipole

Question 6

Define resonance structure

Answer 6

Form either within a functional group or by donating or withdrawing electrons from a neighboring atom
Driving force is stability

Question 7

What are key points of the inductive effect?

Answer 7

F, O, Cl and N have the highest electronegativities of all atoms and are commonly encountered in drug molecules
Oxygen will inductively attract (withdraw) electrons from all other atoms (except F)
O, N, and the halogens will inductively attract electrons from C
C will attract from H

Question 8

Is oxygen ALWAYS an electron withdrawing group?

Answer 8

Depends on the functional group it is attached to

In general, if the oxygen is in a linear chain not next to resonance capable groups it will be EW

Question 9

What are can donate electrons to an aromatic ring?

Answer 9

FGs that contain an atom with a lone pair of electrons

Question 10

What are usually electron donating groups?

Answer 10

Electronegative atoms with lone pairs attached to a phenyl ring
(excluding alkyl grops)
Hydrogens

Question 11

Common EWGs?

Answer 11

Halogens, CF3 and positively charged functional groups
Hydroxyl, sulfhydryl and ether groups when NOT adjacent to a aromatic or double bond
Ether, amide, ester, aldehyde, alcohol, thiol, nitro, nitrile, sulfonamide

Question 12

Common EDGs?

Answer 12

Ethyl

Question 13

Define solvation

Answer 13

uniform distribution of a compound in solvent and is achieved by separation of charge

Question 14

Define overall solubility

Answer 14

Sum of contributions from all the FGs

Question 15

What contributes to Water solubility?

Answer 15

Ability of a FG to ionize or form H-bonds

Question 16

Define acid

Answer 16

proton donor

more positive the H the more acidic

Question 17

Define base

Answer 17

proton acceptor

the more electron density (negative charge) on an atom the more basic

Question 18

Adding bulky groups to a drug molecule can have a number of benefits such as?

Answer 18

Increased selectivity
Enhanced binding interactions
Alteration of rate of metabolism

Question 19

Free rotation vs locked?

Answer 19

Free rotation in a drug means that it will be active only part of the time when it is in the active conformation
Locked in a drug means that it will be active all the time because of the inability to change its conformation

Question 20

Steric hindrance and metabolism

Answer 20

Metabolism of a drug requires it to interact with an enzyme that catalyzes its metabolism
Steric hindrance is a strategy used to block of slow a specific pathway

Question 21

What is another name for stereocenters?

Answer 21

Chrial centers

Asymmetric carbons

Question 22

Define stereocenter

Answer 22

Carbon atom with four bonds to different substituents
Non-super imposable mirror images
R: clockwise
S: counterclockwise