Why does diethyl malonate undergo alkylation?

Why does diethyl malonate undergo alkylation?

The a hydrogen atom of diethyl malonate is sufficiently acidic to be deprotonated by ethoxide ion. Subsequent alkylation with a primary or secondary alkyl halide yields an alkylated malonate ester. Acid catalyzed hydrolysis of the alkylated product yields a malonic acid that decarboxylates when heated.

Can be prepared from diethyl malonate?

Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes….Diethyl malonate.

ChemSpider 13863636
ECHA InfoCard 100.003.006
EC Number 203-305-9
MeSH Diethyl+malonate

How is diethyl malonate synthesis discuss?

The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha (directly adjacent) to both carbonyl groups, and then converted to a substituted acetic acid.

What is the use of diethyl malonate?

Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital.

Which of the following is necessary for the synthesis of diethyl malonate *?

To prepare compound (I), 3,4,6-trifluoro-5-methoxybenzoyl chloride (1) is reacted with diethyl malonate (2) in a mixture of absolute ethanol and toluene in the presence of magnesium ethoxide as a base to give diethyl (3,4,6-trifluoro-5-methoxybenzoyl)-malonate as a crude product, followed by partial hydrolysis and …

How does malonate affect cellular respiration?

It decreases cellular activity. Malonate is a competitive inhibitor of the enzyme succinate dehydrogenase: it binds to the active site of the enzyme without reacting, and so competes with succinate, the substrate of the enzyme. Thus chemical malonate decreases cellular respiration.

What is the mechanism of action of malonate?

Malonate induces mitochondrial potential collapse, mitochondrial swelling, cytochrome c (Cyt c) release and depletes glutathione (GSH) and nicotinamide adenine dinucleotide coenzyme (NAD(P)H) stores in brain-isolated mitochondria.

How does malonate affect ATP production?

Malonate has been shown to cause dose-dependent neurotoxicity both ‘in vivo’ and ‘in vitro’ by inhibition of succinate dehydrogenase and depletion of striatal ATP (Beal et al., 1993; Greene & Greenamyre, 1995; Stokes et al., 2001, Van Westerlaak et al., 2001) resulting in neuronal depolarization and secondary …