Frequent Mistakes Flashcards
What is an acetyl group?
CH3-C=O-R
What are STP? When are these used?
0 T, 1 atm
used for gas law calculations
What are standard conditions? When are these used?
25 T, 1 atm, 1 m
used in thermochemistry
Which have the highest boiling/melting point: saturated or unsaturated fatty acids?
Saturated!
What is the ONLY reaction element that will be changed by an enzyme?
ENZYMES WILL NEVER CHANGE THE POTENTIAL ENERGY, INITIAL STATE, AND FINAL STATE OF A REACTION. THEY WILL ONLY CHANGE THE ACTIVATION ENERGY OF A REACTION (by lowering the energy of the transition state)
What happens when you heat an alcohol?
Dehydration
How does temperature affect KMnO4?
hot KMnO4 → VERY strong oxidizing agent → would break double bonds. VS cold KMnO4 → would just add OH groups to the double bond.
How do H bonds affect boiling/melting points?
H bonding –> stronger intermolecular forces –> stronger surface tension –> higher melting/boiling point
What element is lead?
Pb
What does inert mean?
Cannot react with anything!
What are the 5 conditions for a compound to be aromatic?
- Cyclic
- Planar
- Conjugated
- 4n + 2 pi electrons
- the ring needs at least one unhybridized p-orbital
What to do when asked which molecule will have the highest melting point ?
Imagine what they would be like at room temperature
Which has the highest melting/boiling point: covalent or ionic compounds? Why?
Ionic because they have stronger intermolecular interactions
What is the exact thermochemistry definition of the boiling point?
The temp at which the vapor pressure of the liquid equals the ambient pressure
Which compounds have extremely low boiling points?
Noble gases
Which compounds have very high melting and boiling points?
Transition metals
What does denaturation mean?
Loss of tertiary structure
What are the 2 types of denaturation?
- Heat
2. Solutes
What happens during heat denaturation?
The kinetic energy of the protein increases and overcomes the hydrophobic interactions holding the protein together, so it unfolds
What happens during solute denaturation?
The solute interferes with the forces that hold the protein together directly in the secondary, tertiary, and quaternary structures
What is the effect of SDS on a protein?
Denaturation by solubilizing proteins
What are the 6 factors contributing the a protein’s tertiary structure?
- Disulfide links (cysteine)
- Ionic interactions between acidic and basic side chains
- H bonds
- Van der Waals
- Hydrophobic side chains pushed inside
- Proline kinks
What bonds does urea break in proteins?
H bonds
What bonds do salts or pH changes break in proteins?
Ionic bonds
What bonds does mercaptoethanol break in proteins?
Disulffide links
What bonds do organic solvents break in proteins? What are 2 examples?
Hydrophobic forces
Ethanol and methanol
How to determine the limiting reagent?
Need to identify the reactant with the least amount of moles at the beginning of the reaction
What is the equil constant for gases equal to?
Kp = (Pc)^c x (Pd)^d / (Pa)^a x (Pb)^b
What is the equil constant equal for in terms of rate constants? Where are the rate constants from?
Kc = k1 x k2 x k3 / k-1 x k-1 x k-1
For the rate equations
How does a decrease in pressure affect a reaction’s equilibrium?
The side with more moles of gas will be favored
How does a decrease in volume affect a reaction’s equilibrium?
The side with less moles of gas will be favo`red
Does an increase in k1 mean an decrease in k-1?
No because a catalyst could increase both reactions
How do I know if a compound is an acid or a based based on its Ka?
Ka>10^-7 = acid
What is NH3?
A base!
What is an imine group?
C=N
What does aliphatic mean?
Not aromatic
What is tautomerization?
The movement of an alpha H and movement of a double bond
What is the purpose of the Benedict’s reagent? How does it work? What is its formula?
To detect the presence of a reducing sugar –> red precipitate of Cu2O
Cu(OH)2
What is a reducing sugar?
A carbohydrate that is able to be oxidized meaning it contains a hemiketal or hemiacetal
What is a lactone? How is it formed? What is lost
A cyclic ester with a carbonyl on the anomeric C
Formed through intermolecular esterification of a molecule with a carboxylic acid and alcohol group
The carboxyl OH is lost, forming H2O
What is the purpose of the Tollen’s reagent? How does it work? What is its formula?
To detect the presence of a reducing sugar
Precipitate of silver (s)
Ag(NH3)2+
What is the purpose of a Grignard reagent? What is the formula? What is a required condition for this to happen?
To add the R group to a molecule: CO2, carbonyl (C=O –> C-OH)
RMgX (halide)
No water, or else the reagent would react with it
What is the Henderson-Hasselback equation?
pH = pKa + log [base]/[acid] pOH = pKb + log [HB+]/[B]
What is a lactam?
A cyclic amide
What is a transesterification?
The swapping of the R(-O) group between an alcohol and an ester
What is saponification?
The mixing of fatty acids with NaOH or KOH resulting in a salt
What is a fatty acid?
Long chain carboxylic acid
What kind of compounds can decarboxylate when heated? What is happening here?
Beta keto acids and beta dicarboxylic acids
One of the carbonyl Os takes the H from the other carboxylic acid
How are esters formed?
Nucleophilic acyl substitution with carboxylic acids and alcohols
What is a nucleophilic acyl substitution?
Nucleophilic attack at the carbonyl –> opening of the carbonyl –> elimination of the leaving group –> carbonyl reformation
What is an esterification reaction?
Condensation reaction between a carboxylic acid and an alcohol
What is the formula of an ether?
R-O-R’
In what type of solution are nucleophilic acyl substitutions favored?
Basic and acidic solutions
What happens when a carboxylic acid reacts with ammonia (NH3)?
Amide formation (condensation)
What happens when you heat dicarboxylic acids or 2 carboxylic acids? Explain the mechanism
Anhydride formation (condensation) One OH group attackks the carbonyl of the other
Should a nucleophile be more or less substituted?
LESS
What is LDA?
A strong base
What is the least reactive carboxylic acid derivative?
Amides
What happens when you mix an amide and water? What if you add a base?
NADA! Not reactive enough. Need for a base or acid –> it will become a carboxylic acid
Water + ester = ?
Carboxylic acid
What does [something]dimer mean?
Two of the same [something]
What is the chemical basis of Markovnikov’s rule?
When adding H2O to a double bond: creating the most stable carbocation → addition of the Nu to the most substituted C.
How can you test if a molecule is polar?
Try to dissolve it in water
What is a benzyl group?
Benzene right with a methyl group
What is toluene?
A benzyl = nonpolar solvent
What solvent is needed in Grignard reactions? 2 options
THF
What is DMF?
Dimethylformamide = polar aprotic solvent
Is chloroform a polar or nonpolar solvent?
Nonpolar!
Is diethyl ether a polar or nonpolar solvent?
nonpolar
How is polarity measured? 2 ways
- Dielectric constant = permitivity
2. Measuring the dipole moment
What are polar protic solvents
They contain O-H or N-H bonds
How does one form a Grignard reagent?
Alkyl halide + Mg in diethyl ether
What is the structure of acetone? Is it a polar or nonpolar solvent?
CH3-C=O-CH3
Polar
What is DMSO?
Dimethylsulfoxide = polar aprotic solvent
What is MeCN?
Acetonitrile = polar aprotic solvent
What kind of solvent is needed in nucleophile/electrophile reactions?
Polar aprotic solvents
What types of solvents are most likely to participate in reactions?
Polar protic solvents
What kind of compounds are polar protic solvents? 4 examples
NH3, alchohols, carboxylic acids, and H2O
What are the 3 characteristics of an SN1 reaction? What is another name for it?
- 2 steps (1st one is rate-limiting and the leaving group leaves)
- Product: racemic mixture
- More substituted C → the more reactive
Unimolecular
What are the 4 characteristics of an SN2 reaction? What is another name for it?
- 1 step = concerted reaction
- back-side attack
- Less substituted C → the more reactive
- Inversion of relative configuration
Bimolecular
How to order from highest to lowest nucleophilicity?
- Between molecules with the same attacking group: will parallel basicity: the most basic and the most negative will be the better nucleophile
- Between molecules with different attacking groups: compare the groups by relative electronegativities of the central atom: the less electronegative, the better nucleophile
How to order from highest to lowest electrophilicity?
The better electrophile will have a better leaving group:
- weak bases = conjugate bases of strong acids
- the more electronegative, the better the leaving group
How can one protect aldehydes and ketones from reacting?
By using diols
How does replacing an O for an N affect the oxidation state?
Remains the same!
How to compare the boiling points of different alcohols?
Longer C chain = more H bonds = more Van der Walls forces = higher boiling point
What is the oxidation order of phenols?
hydroquinone (with OH groups)
quinone (with C=O groups)
hydroxyquinone (with both)
What is a geminal diol?
two OHs on 1 C!
What does imines tautomerize to? Which is the more common tautomer?
Enamines
Imines