Organic Chemistry: Alcohols, Carbohydrates, Carboxylic Acids, and Lipids

Flashcards covering the key concepts of oxidation of alcohols, carbohydrates, carboxylic acids, and lipids.

What are the common reagents that act as strong oxidants for alcohol oxidation?

H₂O₂, Na₂Cr₂O₇/K₂Cr₂O₇ (+ H₂SO₄), CrO₃ (+ H₃O⁺), KMnO₄, O₃, nitric acid, hypochlorite, perchlorate/chlorate, persulfate.

What is the product of oxidizing a primary alcohol (1°) under strong oxidizing conditions?

Primary alcohol oxidizes to aldehyde, then to carboxylic acid.

What is the oxidation outcome of a secondary alcohol (2°)?

Secondary alcohol oxidizes to a ketone.

What happens to a tertiary alcohol (3°) when oxidized?

No reaction occurs; tertiary alcohols do not oxidize.

What does the oxidation of a hemiacetal lead to?

The hemiacetal behaves like a primary alcohol and oxidizes to an ester.

How do primary alcohols usually eliminate when dehydrated?

They typically undergo E2 elimination to form terminal or internal alkenes.

What is the major product formed from the dehydration of a secondary or tertiary alcohol?

The major product is the most substituted alkene (Zaitsev product).

What is Markovnikov's rule regarding the hydration of alkenes?

In hydration, hydrogen adds to the carbon with more hydrogen atoms, and hydroxyl (OH) adds to the more substituted carbon.

What is formed when an alcohol reacts with phosphoric acid?

A phosphate ester is formed, with the structure RO–P(=O)(OH)₂.

In the formation of glycosidic linkages, what determines if the linkage is α or β?

The orientation of the glycosidic -OR group at the anomeric carbon relative to the CH₂OH group; cis is β and trans is α.

How do you determine the D or L configuration in Fischer projections?

Find the chiral center farthest from the carbonyl; if the OH is on the right, it is D; if on the left, it is L.

What type of reaction occurs during Fischer esterification?

Carboxylic acid reacts with an alcohol in the presence of acid to form an ester and water.

What is the result of acid-catalyzed hydrolysis of an ester?

The ester is converted back into a carboxylic acid and an alcohol.

What is saponification in the context of ester hydrolysis?

Saponification is the base hydrolysis of an ester, resulting in a carboxylate salt and an alcohol.

What is the outcome of acidic hydrolysis of triacylglycerol (TAG)?

TAG is hydrolyzed to form glycerol and three fatty acids.

What happens during the hydrogenation of unsaturated triacylglycerols?

The double bonds in fatty acyl chains are reduced to single bonds, resulting in fully saturated chains.