2 Basic Organic & Medicinal Chemistry Flashcards Preview

AS - N927 Chem/Physics > 2 Basic Organic & Medicinal Chemistry > Flashcards

Flashcards in 2 Basic Organic & Medicinal Chemistry Deck (27)
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1

Hydrocarbon

Alkane or Alkyl group (single bond) C-C-C
Alkenes - unable to rotate Ø chiral (double bond) C=C
Alkynes (triple bond) C≡C
Aromatic or phenyl group
Benzene ring
C+H equal sharing d/t similar electronegativity
Non-polar covalent
No hydrogen bonding
Longer chain ↑ Van der Waals ↑ attraction ↑ IMF
Insoluble (hydrophobic/lipophilic)

2

Chemical Structure Naming

1 Meth-
2 Eth-
3 Prop-
4 But-
5 Pent-
6 Hex-
7 Hept-
8 Oct-
9 Non-
10 Dec-

3

Ether

R-O-R
CH3-O-CH2-CH3
Slightly polar (dipole)
Electronegativity O (3.44) C (2.55)
Soluble

4

Aldehyde

(-al)

ll
R-C+-H
Carbonyl group C=O
Polar (dipole)
Soluble

5

Ketone

(-one)

ll
R-C+-R
Polar (dipole)
Soluble

6

Ester

(-oate)

ll
R-C+-O¯-R+
Alcohol & carboxylic acid
Polar (dipole)
Soluble

7

Amine

(-ine)
Nitrogen
R-NH-R
NH3 (Ammonia)
NH4 (Ammonium)
1° 2° 3°
Quaternary - permanent + charge (hydrophilic)
Polar (hydrophilic/lipophobic)
1° & 2° hydrogen bonding
N-H dipole
Weak base - accepts H+ ion
↑ lipophilicity w/ each C attached to N
3° most lipophilic d/t unable to H+ bond

8

Alcohol/Phenol

(-ol)
R-O¯-H+
OH > electronegativity than NH
1° 2° 3°
Polar (dipole)
Hydrogen bonding
↑ BP/MP
Soluble
Phenyl w/ -OH (hydroxyl group)

9

Carboxylic Acid

(-oic acid)

ll
R-C+-O¯H+
Carbonyl & alcohol
Polar (dipole)
Hydrogen bonding
Soluble

10

Amide


ll
R-C+-NH2
Carboxylic acid derivative
Nitrogen replaces hydroxyl group
Polar (dipole)
Hydrogen bonding
Soluble

11

Polarity/Solubility

Polar
Most polar / highest BP / Most soluble
↑ BP/MP
↑ length ↓ solubility
Impacted by pH (H+ ion concentration)

12

INTERmolecular Bonds

Hydrogen
Van der Waals (London dispersion forces)
Dipole-dipole

13

Hydrogen Bonding

INTERmolecular bond
Between like molecules or H2O
H+ bond w/ group 7 halogens → dipole
Unequal sharing
Form weaker bond w/ atom¯
Influences BP/MP and therefore solubility

14

Van der Waals

INTERmolecular bond
aka London dispersion forces
Momentary dipoles
Not technically bonds
Longer chain - VdW more likely to form
↑ BP/MP (more likely to be in solid state)

15

Dipole-dipole

INTERmolecular bond
When e¯ spends majority time around one atom over the other
δ¯ δ+

16

INTRAmolecular Bonds

Covalent - polar/non-polar
Ionic

17

Ionic Bond

INTRAmolecular bond
Complete valence e¯ transfer
+/- charge
> 1.8 electronegativity difference
NaCl (3.04-0.9=2.19)

18

Covalent Bond

INTRAmolecular bond
Share e¯ between atoms (electronegativity)
Polar/non-polar

19

Polar Covalent

Unequal e¯ sharing or dipole
0.4 - 1.8 electronegativity difference
C-O (3.44-2.55=0.89)

20

Non-polar Covalent

Equal e¯ sharing
< 0.4 electronegativity difference
C-H (2.55-2.2=0.35)

21

Bond Strengths

Strongest = Covalent
Ionic
Hydrogen
Hydrophobic
Weakest = Van der Waals
↑ # bonds ↓ distance b/w atoms ↑ strength
3 > 2 > 1

22

Phase 1

OIL RIG
Oxidation lose e¯
Reduction gain e¯
Hydrolysis (occurs in blood)
Goal: ↑ polarity

23

Phase 2

Conjugate compound w/ another

24

# Bonds

C = 4
N = 3 or 4
S = 2, 4, 6
O = 2

25

FON

Fluorine
Oxygen
Nitrogen
Polar ჻ soluble

26

Acids in Alkaline Solution

Alkaline solution ↓ H+ concentration
Acid more likely to donate H+ (or dissociate)
↑ polarity ↑ solubility

27

Bases in Acidic Solution

Acidic solution ↑ H+ concentration
Bases more likely to accept H+ (or associate)