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Basic Information

Property	Value
Common name	2‑butanone (also called methyl ethyl ketone, MEK, or simply "butanone")
Molecular formula	C₄H₈O
Molar mass	72.11 g mol⁻¹
Boiling point	79.6 °C (173.7 °F)
Melting point	–107 °C (–162 °F)
Density (20 °C)	0.791 g cm⁻³
Solubility in water	100 % at 25 °C (miscible)

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1. What is Butanone?

Butanone, or butan-2-one, is the simplest α‑keto compound that has four carbon atoms and a methyl group on the second carbon. Its structure can be written as:


CH3–CO–CH2–CH3

The "α‑ketone" means the carbonyl (C=O) is directly adjacent to a methylene group (–CH₂–). This placement gives butanone its unique reactivity.

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2. Chemical Properties

Property	Detail
Molecular formula	C₄H₈O
Boiling point	~56 °C
Density	0.81 g cm⁻³ (at 20 °C)
Solubility	Miscible in water, ethanol, acetone; soluble in most organic solvents
Odor	Sweet, fruity, slightly resinous
Stability	Stable under normal conditions; decomposes at high temperatures (>250 °C).
Reactivity	Acts as a mild carbonyl (aldehyde) compound. Reacts with nucleophiles forming addition products.

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3. Applications of 4‑Methyl‑1,2‑oxazole

Field	Typical Uses	How 4‑Me‑Oxy is Incorporated
Organic Synthesis	Synthetic building block – used to generate heterocycles, lactones, or to mask a reactive aldehyde.	The oxazole ring can be opened (via nucleophilic attack) to give a substituted aldehyde or amide after reduction/oxidation.
Pharmaceuticals	Lead compounds for anti‑inflammatory, antiviral, anticancer agents.	Many drug candidates incorporate the oxazole core due to its metabolic stability and ability to form hydrogen bonds with protein targets.
Materials Science	Conductive polymers or optical materials.	Oxazoles can contribute to electron delocalization in polymer backbones, improving conductivity and optical properties.

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3. Key Reactions Involving the Oxazole Ring

Below are some typical transformations that convert an oxazole into a functional group of interest. For each, a concise mechanism is provided.

Transformation	Product	Mechanism Overview
N‑Oxidation → N–oxide	1‑Hydroxy‑2‑(alkyl)oxazoline	Oxidant (e.g., mCPBA, H₂O₂) forms a peracid or peroxide that attacks the nitrogen lone pair, creating an N‑oxide.
Ring‑Opening by Nucleophiles	1‑Hydroxy‑2‑(alkyl)oxazoline → β‑hydroxy alcohol + amine	Protonation of the oxazole oxygen makes it a good leaving group; nucleophile attacks at C‑3, leading to cleavage.
Acidic Hydrolysis	Oxazole → Carboxylic acid + amine	Strong acids protonate the ring, facilitating water addition at C‑2 or C‑3 and subsequent rearrangement to open the ring.
Reduction (LiAlH₄)	Oxazole → β‑hydroxy alcohol + secondary amine	LiAlH₄ reduces both the heteroaromatic ring and the C=O bond, leading to cleavage of the C–N bond.

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3. Detailed Mechanism for Hydrolysis of a Representative Oxazole

Substrate (example):

A simple 2‑(methyl)‑oxazole:


O
/ \
|   |
|   N
\ /
CH3

Step‑by‑Step

Step	Transformation	Electron Flow	Key Intermediates/Factors
1. Protonation of the ring oxygen (acidic medium)	Oxazole becomes an oxazolium ion	H⁺ adds to O, pushing electrons onto N and C	Increases electrophilicity at C‑2 (adjacent to protonated O)
2. Nucleophilic attack by water at C‑2	Water attacks electrophilic C‑2, opening the ring	Lone pair of H₂O attacks C‑2; electrons shift from N=C bond to N, breaking N–C(=O) bond	Forms tetrahedral intermediate with –OH on former C‑2
3. Proton transfer and collapse of intermediate	Intermediate collapses, www.worl.com restoring aromaticity and generating a carboxylate group	Loss of proton from N (or H₂O), re-aromatization; cleavage of N–C bond yields an amide or acid depending on conditions	Produces a substituted benzoic acid derivative with –OH at position 2
Final product	The ring is opened, yielding a phenolic carboxylic acid with substituents determined by the original alkyl groups	The overall process is a reductive cleavage of the C–N bond in the aromatic system	This transformation yields an open-chain benzoic acid derivative that can be further functionalized