Term
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Definition
Amphoteric - act as acid and base
All have chiral center (x/ glycine)
L is the natural occurig form (NH2 on L)
In neutral solution form zwitterion - dipolar ion at pI (isoelectric pH) |
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Term
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Definition
Equimolar
Mole [OH-] added = Mole [H+] present |
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Term
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Definition
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Term
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Definition
1. COOH deprotonated before NH3
2. 2 moles of base for 1 mole of a.a
3. Buffer capacity is greatest at pKa1 and pKa2 but smallest at pI
4. pH of equivalent point is not usually 7
5. Indicator (weak acid-not involved in rxn) - best when closest to equi. pH
HA(color 1) + H2O -> H3O + A- (color 2)
* if [H3O] > Ka, sln will be color 1 |
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Term
| HENDERSON- HASSELBALCH EQUATION |
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Definition
| pH = pKa - log [con. BASE]/ [con. ACID] |
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Term
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Definition
| EXOthermic rxn -> formation of something stable
Always give Salt and Water
pH DOES NOT equal to 7
Depends on the acidity/basicity of the salt |
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Term
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Definition
1. Weak Acid and salt of its conjugate base or
2. Weak Base and salt of its conjugate acid
3. Use acid with pKa close to pH that you want to maintain
4. Increase [buffer] = Increase Efficiency |
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Term
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Definition
R = CHO, Hydrophobic,↓solubilty, INSIDE or at core of proteins or transmembrane to avoid H2O
Alanine, Valine, Leucine, Isoleucine, Proline, Phenyl alanine, Glycine, Thryptophan |
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Term
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Definition
R= Polar, Uncharged
HydroPHILIC, ↑ solubility, on SURFACE of protein
Methioninine, Serine, Theroine, Cystein, Tyrosine, Asparagine, Glutamine |
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Term
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Definition
| R = COOH group
- at Physiological pH = 7.4
Have 3 distinct pKa's - 3 mole of base is needed for neutralization
Important in substrate binding sites of enzymes |
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Term
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Definition
| R= NH2
+ at physiological pH = 7.4
3 moles of acid is needed to neutralize 1 mole of base
Arginine, Lyscine, Histidine |
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Term
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Definition
| Amino Acid subunits
Peptide bond= Amide bond formed via condensation (water is loss)
Rotation about the C-N bond is limited because resonance give C-N a partial double bond character |
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Term
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Definition
| 1° = sequence of a.a
2° = local structure of neighboring a.a due to H-bonding
α helix (keratin) β pleated sheet
3°= 3D shape of protein due to hydrophilic/Hydrophobic interaction between R groups of a.a
Disulfide bond → loops in protein chain
Proline can't fit into α helix → kink in chain
Fibrous = sheets/long strands (collagen)
Globulous = spherical (myoglobin>
4° = Arrangement of polypeptide subunit (Hemoglobin = 4 subunits) |
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Term
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Definition
| Attached to prosthetic group (organic molecules or metal) |
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Term
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Definition
Loss of 3D (3° structure → random coil state- disruption of INTERmolecular forces)
Due to detergent, change in pH, Temp, [solute]
Some protein can REnature |
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Term
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Definition
| Different in configuration at ONLY ONE carbon |
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Term
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Definition
| Differ in conjugation ONLY at the newly formed chiral center |
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Term
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Definition
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Term
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Definition
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Term
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Definition
Allow α → α + β
or
β → α + β |
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Term
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Definition
| [image]
Hemiacetal + Alcohol → Acetal
Both α and β linkages are formed |
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Term
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Definition
Due to glycosidic linkages between C1-C4, C1-C6 or C1-C2
α or β
In body, enzymes ar eneeded to ensure the right glysidic bond is form.
Without enzymes, reactions are NONspecific and never stopping at disaccharide level |
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Term
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Definition
Cellulose = β 1,4 Structure components of PLANT
Starch = α 1,4(some 1,6) Stored energy in PLANT
Glycogen= α 1,4 (some 1,6) Stored energy in ANIMAL
* Cellulose can't be ingested by human |
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Term
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Definition
| Measure vibrations
- Stretching, bending and rotation of a molecule
- Stretching and bending can be Symmetric or Asymmetric
Light → excited state (3500-300 cm-1 |
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Term
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Definition
| 400-1500 cm-1
Characteristic of a molecule, frequently used to identify a substance |
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Term
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Definition
| DO NOT show in IR because no net change in dipole moment |
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
C-H 2900-3100
C-C 1475-1625 |
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Term
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Definition
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Term
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Definition
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Term
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Definition
(0)C-H 2700-2900
C=O 1725-1750 |
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Term
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Definition
C=O 1700-1750
O-H (broad) 2900-3300 |
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Term
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Definition
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Term
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Definition
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Term
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Definition
Larger sample
NO coupling except between carbons and hydrogens directly attached to them
Spin decoupling: record without coupling of adjacent protons
Show: # of C's with relative chemical environment
# of H's (spin coupling NMR's) |
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Term
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Definition
Pass light, observe Absorbance
Beer Law
A= ebc
Most useful for studying compound wit double bonds and heteroatoms with lone pairs |
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Term
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Definition
Pass light, measure mass of particle
Sample is ruined afterward
1. cation radical decompose → mass/charge ratio
2. base peak = tallest peak (% of 100)
3. Molecular ion peak = highest m/e peak |
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Term
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Definition
| - suffix - ate
1. Polar
2. Able to form H-bond
3. Greater bp than alcohol
4. Acidity is due to resonance stabilization of conjugate base
5. β H's are extremely acidic because its loss → stable carbanion
6. Acidity can be enhanced by adding EN gr. or other potential resonance structre |
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Term
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Definition
| aka CYANIDE
has CN- group = good [NUC-] for 1°, 2° SN2 reactions |
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Term
| SYNTHESIS OF CARBOXYLIC ACID |
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Definition
| 1. Oxidation of alcohol (using KMNO4)
2. Ginard reagents (1 additional C)
3° alkyl halide → carboxylic acid
3. Hydrolysis of nitriles (1 additional C)
CH3Cl → CH3CN→ CH3COOH + NH4- |
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Term
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Definition
| RCOOH + NaOH → ROO-Na+ (soap) + H2O
Soap tends to rearrange into micelles (like mb) with polar head outward and nonpolar tails inward to dissolve grease
Micelle (as a whole) is soluable in water because of polar shell |
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Term
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Definition
| Acyl halide > anhydrides> Esters> Amindes |
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Term
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Definition
= without water
2 ACID → condensation→ Anhydrides |
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Term
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Definition
| [image]
Form from 1° or 2° amine |
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Term
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Definition
| Amides → 1° with loss of carbon[image] |
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Term
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Definition
| ACID + ALCOHOL → ESTER
[image] |
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Term
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Definition
| Fats( triacylglycerols) are hydrolyzed under basic condition |
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Term
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Definition
| prefix amino-
Boiling point is lower than alcohol because N has lower EN
3° amine can't H-bond thus have lower bp than 1° and 2°
sp3 - able to
undergoes nitrogen inversion (low Ea - 6 kcal/mol)
* optically active if inversion is hindered
Weak Acid |
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Term
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Definition
| Nitroglycerine relaxants: relieve coronary arteries spasms for chest pain
Nitrous oxide relaxants : dental anesthetic |
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Term
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Definition
| Primary Akyl halide → 1° amine (no side products)
[image] |
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Term
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Definition
| aka Hoffmann Elimination [image] |
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Term
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Definition
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Term
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Definition
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Term
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Definition
Most Different
Different in MOLECULAR FOMRMULA |
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Term
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Definition
Chiral = nonsuperimposable
Achiral - super imposable
*rotation doesn't change chirality
Differences in chirality can produce enantiomers (nonsuperimposed mirror images) or diastereomers ( diff, in chirality but not mirror images) |
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Term
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Definition
Different around DOUBLE BOND
cis vs. trans
Different in physicial properties (mp or bp)
Similar Reactivity |
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Term
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Definition
| Chiral molecules
Identical properties but different in optical activity |
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Term
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Definition
| Chiral but not optical active because of internal plane of symmetry |
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Term
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Definition
Ability to rotate plane in polarized light
+ dextrorotary - R
- Levorotary - L
α (angle of rotation) - observed oration/ [] g/ml x leight dm |
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Term
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Definition
| Mixture of equal concentration of + and = enantiomers |
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Term
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Definition
2+ chiral centers
Different in chirality but not mirror images
R,S vs. R,R |
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Term
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Definition
| Different ONLY by rotation about 1 or more single bond
"gauche" vs " eclipse" |
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Term
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Definition
↑ chain length → ↑ bp, mp , density
&branching → ↓ bp, mp, density
Stablity of carbocation and free radical
3° > 2° > 1° > methyl |
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Term
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Definition
Molecules is broken down by heat
aka: craking → radicals |
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Term
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Definition
1. Basicity
RO-> HO->RCO2-> ROH> H2O
2. Size and Polarity
- Protic solution (able to H-bonding)
CN-> I-> RO-> HO-> Br-> Cl-> F-> H2O
- Aprotic solution
F-> Cl> Br> I
3. Larger atom = better Nuc |
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Term
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Definition
Weak acid = best
I> Br > Cl > F |
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Term
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Definition
| Rate is dependant on the formation of carbocation
Condition is chosen so that the second step is IRREVERSIBLE
rate = k[S] |
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Term
| ACCELERATE FORMATION OF CARBOCATION |
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Definition
| 1. Structural factors: more subs → more stable carbocation → better SN1
2. Solvent effect: Polar Solvent (better at surrounding and isolating ions)
Protic polar is best (solvation stabilize intermediate)
3. LG : weak bases dissociate more easily |
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Term
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Definition
| Well defined species with a finite lifetime |
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Term
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Definition
| Theoretical structure used to define mechanism |
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Term
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Definition
SN1
2 steps
Favored : polar PROTIC solvent
3>2>1
racemic products (loss of optical activity)
Favored the use of bulky [Nuc]
SN2
1 step - concerted
Favor: polar APROTIC solvent
1>2>3
rate = k[RX][Nuc]
Optically active / inverted products |
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