Alcohols and Phenols Flashcards
Put the following in order from most to least acidic: Propanoic acid Propanone Propanethiol Propanol
Propanoic acid Propanethiol Propanol Propanone
True or False: Thiols are more acidic than alcohols
True
True or False: Ketones are more acidic than alcohols
False, they are less acidic
gain of bonds to oxygen (as in the conversion of a secondary alcohol to a ketone) or the loss of bonds to hydrogen
Oxidation
the loss of bonds to oxygen or the gain of bonds to hydrogen
reduction
processes in which two substituents are lost from a molecule; this typically forms a double bond in their place
Elimination
specific kind of elimination in which a water molecule is removed
Dehydration
True or False: Carboxylic acids only form from the oxidation of primary alcohols
True
True or False: You can form a carboxylic acid by oxidizing cyclohexanol
False, cyclohexanol is a secondary alcohol, Carboxylic acids only form from the oxidation of primary alcohols
A primary alcohol reacts with pyridinium chlorochromate. The product of this reaction will have a carbon-oxygen bond order that is _____ higher than that of the original alcohol.
A primary alcohol has one bond between carbon and oxygen. Reaction with pyridinium chlorochromate (PCC) will convert this alcohol into an aldehyde, which has two carbon-oxygen bonds (in the form of a double bond). Since the product has one more carbon-oxygen bond than the alcohol reactant, the product’s bond order is one higher than the reactant’s bond order, and one is our answer.
True or false: Ubiquinol is more oxidized than ubiquinone.
This statement is false. Ubiquinol is a benzenediol while ubiquinone is a dicarbonyl compound. In other words, ubiquinol is identical to ubiquinone, except that ubiquinol has two -OH groups instead of =O functionalities on the benzene ring. Since R-OH (an alcohol) is more reduced than R=O (a carbonyl), ubiquinol is in fact more reduced – or less oxidized – than ubiquinone. Even if you were uncertain of the structure of ubiquinol, you should know that alcohols have the suffix -ol, and alcohols are more reduced than their analogous ketone carbonyl-containing compounds, whose suffix is -one.
True or False: Ortho substituted phenols have more steric hindrance than their meta and para counterparts due to the closeness of the hydroxyl group to the ortho substituent.
True
How do the hydrogen bonds in alcohols impact melting and boiling points?
The intermolecular interactions tend to raise the melting or boiling point
Which will have a higher boiling point and why?
1,3,5-pentanetriol will have a hihger BP due to increase h-bonds
True or False: In acid base chemistry, adding electron withdrawing groups can make an acid stonger while adding electron donating groups make it a weaker acid
True
How does the presence of chlorine impact the acidity of the alcohol depicted?
It will increase the acidity of the alcohol.
Chlorine is an electron withdrawing group meaning that it draws electron density towards it making it more likely for the alcoholic oxygen to deprotonate. It makes oxygen less negatively charged and more stable so the chlorine helps stabilize the conjugate base!
How does the presence of the methyl group impact he acidity of the alcohol depicted?
It decreases the acidity of the alcohol.
