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Example Questions
Example Question #1 : Using Potassium Permanganate
What is the product when 1-propanol is treated with potassium permanganate?
Propanal
Propanoic acid
None of these
1-propanone
No reaction occurs
Propanoic acid
Potassium permanganate is a strong oxidizing agent. It can convert secondary alcohols to ketones. It can also convert primary alcohols to carboxylic acids. 1-propanol has a hydroxy group on carbon 1, so it is primary; thus it will be converted to propanoic acid.
Example Question #2 : Organic Oxidizing Agents
What is the product when 2-butanol is treated with PCC?
2-butanone
1-butanol
2-butanol
1-butanone
None of these
2-butanone
PCC is an oxidizing agent. It converts alcohols to ketones, but is not strong enough to convert primary alcohols to carboxylic acids. 2-butanol has a hydroxy group on its carbon 2. The addition of PCC will convert this hydroxy group into a carbonyl, producing 2-butanone.
Example Question #1 : Using Pcc
What is the product of 1-pentanol when it is treated with PCC?
1-pentanone
2-pentanol
No reaction occurs
Pentanal
None of these
Pentanal
PCC is an oxidizing agent. It converts alcohols to carbonyls, but is not strong enough to convert a primary alcohol into a carboxylic acid. It only converts primary alcohols to aldehydes, and secondary alcohols to ketones. 1-pentanol is a primary alcohol so it will be converted to the aldehyde pentanal.
Example Question #1 : Using Pcc
Which reagent is best-suited to accomplish the given reaction?
PCC
PCC
PCC is an oxidizing agent that reacts with primary and secondary alcohols. However, it is less reactive than potassium permanganate and chromic acid. PCC differs from chromic acid by oxidizing primary alcohols to aldehydes, whereas chromic acid oxidizes primary alcohols and aldehydes to carboxylic acids. The desired product of the reaction given requires that the primary alcohol be oxidized to an aldehyde, so PCC is the best option. is a reducing agent and would have the opposite effect than what is desired, yielding an alkane.
Example Question #2 : Using Pcc
Which reagents are required to drive the given reaction?
This is a two step reaction. In the first step, an alcohol is substituted for the bromine via an reaction. Next, the alcohol is oxidized into a ketone with , a strong oxidizing agent used almost exclusively for converting alcohols into carbonyls.
Example Question #4 : Using Pcc
Which of the following is not true regarding the reagent ?
can oxidize secondary alcohols into ketones
can oxidize primary alcohols into aldehydes
None of these
can oxidize aldehydes into carboxylic acids
can oxidize aldehydes into carboxylic acids
has the capability of oxidizing primary alcohols into aldehydes and secondary alcohols into ketones. However, it cannot oxidize aldehydes into carboxylic acids. To do that, we would need a stronger oxidizing agent such as .
Example Question #2 : Organic Oxidizing Agents
What is the product of the reaction shown?
II
V
I
III
IV
III
First step: PCC oxidizes the primary alcohol to acetaldehyde
Second step: Grignard reagent attacks carbonyl carbon
Third step: Neutralization of the anion forms isoproyl alcohol
Example Question #2 : Using Pcc
Which of the following compounds is not a reducing agent?
is the only compound listed that is not a reducing agent. Pyridinium chlorochromate is a weak oxidizing agent and is often used to oxidize alcohols into carbony compounds. All of the other compounds are similar in that they function as reducing agents.
Example Question #1 : Using Pcc
What would be the product of the given reaction?
The reaction given would give an aldehyde. This type of reaction is called an oxidation reaction. Oxidation of a primary alcohol as in the reaction given by PCC (pyridinium chlorochromate) in (dichloromethane) solvent yields an aldehyde. Like chromic acid, PCC oxidizes alcohols. However, PCC only oxidizes primary alcohols one step up to aldehydes and secondary alcohols to ketones. Chromic acid is a harsher oxidant because it will oxidize aldehydes to carboxylic acids. Below is the mechanism for this reaction:
Example Question #7 : Using Pcc
What would be the product of the given reaction?
The reaction given would give an aldehyde. This type of reaction is called an oxidation reaction. Oxidation of a primary alcohol as in the reaction given by PCC (pyridinium chlorochromate) in (dichloromethane) solvent yields an aldehyde. Like chromic acid, PCC oxidizes alcohols. However, PCC only oxidizes primary alcohols one step up to aldehydes and secondary alcohols to ketones. Chromic acid is a harsher oxidant because it will oxidize aldehydes to carboxylic acids. Below is the mechanism for this reaction: Below is the mechanism:
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