Lactones are cyclic esters in which the carboxylic acid part and the alcohol part are connected to form a ring. One of the most notorious lactones is gamma-butyrolactone (GBL), whose hydrolysis product is the 'date-rape' drug GHB. Draw the structure of GHB.

Verified step by step guidance

1. Understand the problem: Gamma-butyrolactone (GBL) is a cyclic ester (lactone). Hydrolysis of a lactone involves breaking the ester bond by adding water, resulting in a carboxylic acid and an alcohol group.
2. Identify the structure of GBL: GBL is a four-membered ring containing an ester functional group. The ring consists of three carbon atoms and one oxygen atom, with the ester bond connecting the carbonyl carbon to the oxygen in the ring.
3. Apply hydrolysis: During hydrolysis, the ester bond in GBL is broken. The carbonyl carbon forms a carboxylic acid group (-COOH), and the oxygen in the ring forms a hydroxyl group (-OH).
4. Determine the structure of GHB: After hydrolysis, the resulting molecule is gamma-hydroxybutyric acid (GHB). It has a four-carbon chain with a hydroxyl group (-OH) on the gamma carbon (the fourth carbon from the carboxylic acid group).
5. Draw the structure of GHB: Represent the molecule with a carboxylic acid group (-COOH) at one end, a hydroxyl group (-OH) on the gamma carbon, and the remaining carbons forming a straight chain. Ensure the correct placement of functional groups to reflect the hydrolysis product.

Key Concepts

Lactones

Lactones are a class of cyclic esters formed when a carboxylic acid reacts with an alcohol, resulting in a ring structure. They are characterized by their unique cyclic formation, which influences their chemical properties and reactivity. Lactones can vary in size and complexity, with gamma-butyrolactone (GBL) being a notable example due to its significance in both chemistry and pharmacology.

Gamma-Butyrolactone (GBL)

Gamma-butyrolactone (GBL) is a specific type of lactone that is a colorless, odorless liquid with a variety of industrial and pharmaceutical applications. It is known for its ability to hydrolyze into gamma-hydroxybutyric acid (GHB), a substance that has gained notoriety for its use as a recreational drug and in cases of drug-facilitated sexual assault. Understanding GBL's structure and properties is crucial for comprehending its transformation into GHB.

Gamma-Hydroxybutyric Acid (GHB)

Gamma-hydroxybutyric acid (GHB) is a naturally occurring neurotransmitter and a psychoactive substance that is often associated with illicit drug use. It is known for its sedative and euphoric effects, which can lead to misuse and dangerous situations, particularly in social contexts. The structural relationship between GBL and GHB is essential for understanding their chemical behavior and the implications of their use.