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70 Cards in this Set
- Front
- Back
R or S? |
R |
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R or S? |
S |
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What is a Functional Group? |
Group of atoms in a molecule with characteristic behavior |
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What are ADMET properties? |
Adsorption, distribution, metabolism, excretion, toxicity |
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Which intermolecular forces have dipole? (3) |
- ion dipole - hydrogen bonding - dipole-dipole |
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Which is the weakest intermolecular force? |
VDW forces |
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What do VDW forces depend on ? (2) |
- Dipole-dipole (H-bonds) - Ion- dipole |
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Which force can happen between salts and Acids and Bases? |
Ion- ion bonding |
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Which force increases lipophilicity (hydrophobicity)? |
VDW forces |
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What is the bioactive enatiomer called? |
Eutomer |
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E or Z? |
Z/ cis |
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E or Z? |
E/ trans |
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What is the only type of bonding for aliphatic compounds? |
VDW |
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what rxn is happening here to metabolize this alkane? |
beta oxidation |
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What type of intermolecular forces can aromatic rings use? |
VDW and stacking |
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what is this rxn called to metabolize aromatic rings? |
aromatic hydroxylation |
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Do covalently bound halogens make organic compounds more lipophilic or hydrophilic? |
lipophilic |
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what are the functional groups in blue? |
alcohols |
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what type of alcohol is this? |
primary |
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what type of alcohol is this? |
tertiary |
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If an alcohol bonds to itself, what will happen to the BP? |
it increases |
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In general, alcohols are stable. Except when they are in the presence of what? |
oxidizing agents |
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Primary alcohols break down into what? |
aldehydes and then acids |
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Secondary alcohols form? |
Ketones |
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What do tertiary alcohols break down to form? |
They do not react |
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What are the 2 phases of alcohol metabolism? |
Phase 1 = oxidation Phase 2 = conjugation/ glucuronidation/ sulfonation |
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R or S? |
S |
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Which of the following is the most significantintermolecular bonding between twomolecules of alkyl bromides? |
VDW |
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R or S for 7 stereocenters |
1. S 2. R 3. R 4. R 5. S 6. R 7. S |
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What is this functional group? |
phenol |
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If an OH is added to a phenol, how does this affect its solubility? |
more hydrophilic |
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If a methyl is added to a phenol, what happens to its solubility? |
its more lipophilic |
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What makes a phenol more acidic when it reacts with water? |
resonance |
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what is the definition of an acid |
BL: donates a proton L: accepts a lone pair of electrons |
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If an EDG is added to a phenol and it reacts with water, will the pKa be acidic or basic? |
basic, more electron density on the conjugate base anion is not stabilizing therefore it is not acidic |
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What type of aromatic substitution as the best resonance stability? |
para substitution |
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These are examples of what types of groups? |
EDG, they have lone pairs on adjacent pi systems |
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These are examples of what types of groups? |
EWG, they have multiple bonds or have a formal charge that can accept electron density |
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Phenols are weak acids, will they react with weak bases? |
no |
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When phenols react with strong bases they form salts. What type of intermolecular forces will they use? |
ion-dipole |
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phenols are prone to ____________ in air |
oxidation |
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what type of rxn is this? |
oxidation |
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Phase 1 metabolism for phenols consists of waht rxn? |
hydroxylation |
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Phase 2 metabolism for phenols consists of what rxn? |
conjugation with sugars or sulfur atoms OR methylation (MAKES MORE LIPOPHILIC) |
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what type of functional groups are these? |
ethers and thioethers |
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Do pure ethers have high BPs? |
no because they only do VDW forces |
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What type of reaction is this? |
dealkylation/ demethylation |
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Are thioethers more hydrophilic or lipophilic? |
lipophilic b/c sulfur is a strong nucleophile, R groups are non-polar, and sulfur is a large atom |
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What are the different types of thioether metabolism? |
- S-oxidation - S-dealkylation |
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rxn? |
S-oxidation |
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rxn? |
S-dealkylation |
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Functional groups? |
aldehyde and ketone |
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rxn? |
keto-enol tauterism |
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name each of the intermediates |
aldehyde, hemiacetal, acetal |
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name each of the intermediates |
ketone, hemiketal, ketal |
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how are ketones and aldehydes metabolized? |
mainly oxidized with enzymes |
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functional group? |
amine |
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do amines act like acids or bases? |
bases because the lone pair of electrons on the nitrogen act as a proton acceptor |
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If the R groups on an amine are EDGs, does that make the amine more acidic or basic? |
more basic because they add electron density onto the nitrogen and allow it to better accept hydrogen/ donate electrons |
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Without any steric hinderance rank primary secondary and tertiary amines on their basicity |
1<2<3 |
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With steric hinderance rank primary secondary and tertiary amines on their basicity |
1<3<2 |
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What happens in phase 1 metabolism of amines? |
dealkylation |
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What happens in phase 2 metabolism of amines? |
glucuronidation, sulfonation, acetylation |
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rxn? |
acetylation |
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rxn? |
sulfation |
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functional group? |
corboxylic acid |
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when carboxylic acids are in this solvent their solubility increases |
ethanol |
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when the R group on a carboxylic acid is electron withdrawing, what happens to its acidity? |
increases |
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What happens in phase 1 metabolism of carboxylic acids? |
beta-oxidation |
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What happens in phase 2 metabolism of carboxylic acids? |
glucuronidation, amino acid conjugation |
