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MCAT Org. Chem Ch. 5
| Question | Answer |
|---|---|
| Alcohols | Have the general form, ROH, and are named with the suffix, -ol. If they are not the highest priority present, they are given the prefix, hydroxy- |
| Phenols | Benzene rings with hydroxyl groups. They are named for the relative positions of the hydroxyl groups. (ortho, meta, para) |
| Ortho- | Adjacent carbons |
| Meta- | Separated by one carbon |
| Para- | On opposite sides of the ring |
| Properties Of Alcohol | They can hydrogen bond, raise their boiling and melting points relative to corresponding alkanes. |
| Hydrogen Bonding And Solubility Of Alcohols | H-bonding increases the solubility of alcohols. |
| Reason Why Phenols Are More Acidic | They are more acidic because the aromatic ring can delocalize the charge of the conjugate base. |
| Reason Why Electron-donating Groups (like Alkyl Groups) Decrease Acidity | Because they destabilize negative charges. |
| Reason Why Electron-withdrawing Groups (ex: Electronegative Atoms and Aromatic Rings) Increase Acidity | Because they stabilize negative charges. |
| Pyridnium Chlorochromate (PCC) | Only substance used to oxidize primary alcohols to aldehydes. Otherwise, the primary alcohols will be oxidized all the way to carboxylic acids by stronger oxidizing agents. |
| How Secondary Alcohols Can Be Oxidized To Ketones | This can be done by any common oxidizing agent. |
| Why Alcohols Are Converted To Mesylates Or Tosylates | To make them better leaving groups for nucleophilic substitution reactions |
| Mesylates | Contain the functional group, -SO3CH3, which is derived from methanesulfonic acid. |
| Tosylates | Contain the functional group, -SO3C6H4CH3, which is derived from toluenesulfonic acid. |
| How Aldehydes or Ketones Can Be Protected | Convert them into acetals or ketals |
| Process Of How Aldehydes Or Ketones Can Be Protected | 1. Two equiv's of alcohol or a dialcohol are reacted with carbonyl to form the acetal or ketal |
| Acetal | Primary carbon with two -OR groups and a hydrogen atom |
| Ketal | A secondary carbon with two -OR groups. |
| Note About Other Functional Groups In The Aldehyde / Ketone Compound During Acetal or Ketal Rxn | They can be reacted without having effects on the newly formed acetal or ketal |
| Deprotection | Process of converting an acetal or ketal back to a carbonyl by catalytic acid |
| Quinones | Synthesized through oxidation of phenols. They are resonance-stabilized electrophiles. |
| Phylloquinone | Vitamin K1, an example of a biochemically relevant quinone |
| Menaquinone | Vitamin K2, an example of a biochemically relevant quinone |
| Hydroxyquinones | Produced by oxidation of quinones, adding a variable number of hydroxyl groups |
| Ubiquinone (Coenzyme Q) | A biologically active quinone that acts an electron acceptor in Complexes I, II, and III of the electron transport chain. |
| Ubiquinol | Reduced form of Ubiquinone. |
Created by:
SamB91
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