Skip to main content
Ch.17 Carboxylic Acids and Their Derivatives
McMurry - Fundamentals of General, Organic, and Biological Chemistry 8th Edition
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoMcMurry 8th EditionCh.17 Carboxylic Acids and Their DerivativesProblema 64
Capitolo 17, Problema 64

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.

Guida verificata passo dopo passo
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.
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.
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).
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).
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.

Concetti chiave

Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.

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.
Video consigliato:
Percorso guidato
2:43
Oxidoreductases Concept 4

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.
Video consigliato:
Percorso guidato
02:16
Gamma Emission Reaction Example

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.
Video consigliato:
Percorso guidato
02:16
Gamma Emission Reaction Example
Pratica correlata
Domanda del libro di testo

Household soap is a mixture of the sodium or potassium salts of long-chain carboxylic acids that arise from saponification of animal fat.

b. Draw the structures of the soap molecules produced in the following reaction:

641
views
Domanda del libro di testo

Give systematic names for the following structures and structures for the names:

a. 3-Methylpentanamide

756
views
Domanda del libro di testo

Give systematic names for the following structures and structures for the names:

b. N-Phenylacetamide

759
views
Domanda del libro di testo

When both the carboxylic acid and the amine are in the same molecule, amide formation produces lactams. A lactam is a cyclic amide, where the amide group is part of the ring. Draw the structure of the product(s) obtained from acid hydrolysis of these lactams.

a.

756
views
Domanda del libro di testo

A simple polyamide can be made from ethylenediamine and oxalic acid (Table 17.1). Draw the polymer formed when three units of ethylenediamine reacts with two units of oxalic acid.

713
views