Alcohols Flashcards
Which has a lower pKa Phenols or non aromatic alcohols?
Phenols have a increased acidity due to resonance and the electron-withdrawing character of the phenol aromatic ring.
Greater acidity=
Lower pKa and Higher Ka
2 groups on adjacent carbons are called?
Ortho- or o-
2 groups separated by a carbons are called?
Meta- or m-
2 groups on opposite sides are called?
Para- or P-
What will happen to a primary and secondary alcohols in the presence of a strong oxidizing agent?
Primary- oxidize completely to carboxylic acid
Secondary- Convert to a ketone
What are examples of strong oxidizing agents
(Na2Cr2O7 or K2Cr2O7)/ H2SO4
Jones Oxidation: CrO3, H2SO4/ Acetone
How can a primary alcohol be oxidized to aldehydes?
PCC (pyridinium chlorochromate)
What is the purpose of mesylate and tosylate?
They are used to convert an alcohol into a better leaving group and used a protecting groups
How can Aldehydes and ketones be protected using alcohols?
turn them into acetals or ketals and then converted back via deportation
Mesylates contain the functional group
-SO3CH3 which is derived from methanesulfonic acid
Tosylates contain the functional group
-SO3C6H4CH3 which is derived from toluenesulfonic acid
Acetals
Primary C with 2 -OR group and H
Ketals
Secondary C with 2 OR groups
How are quinones generally produced?
Oxidation of Phenols
How are hydroxyquinones produced?
Produced by oxidation of quinones, adding a variable number of additional hydroxyl groups
What chemical properties of ubiquinone allow it to carry out its biological functions?
Ubiquinone has conjugated rings, which stabilize the molecule when accepting electrons. Additionally, the long alkyl chain in the molecule allow for lipid solubility, which allows the molecule to function in the phospholipid bilayer.
What is the reduced form of ubiquinone
Ubiquinol
Examples of biochemically relevant quinones
Vitamin K1 (Phylloquinone) and Vitamin K2 (menaquinones)
