☰ Contents · Chemistry (Organic chemistry)

Ketones

Lessons 25 · 1 lessons · A. Mutalibov, E. Murodov, S. Masharipov, H. Islomova. Organic Chemistry, Grade 10, 1st edition. G‘afur G‘ulom Publishing House, Tashkent, 2017
25

Ketones: preparation and properties

Textbook: pp. 99–102
GoalState the structure, naming, preparation and properties of ketones and tell them apart from aldehydes.
New words
ketones · ketonlaracetone (propanone) · aseton (propanon)secondary alcohol · ikkilamchi spirtcarbonyl group · karbonil guruh
Explanation

Compounds in which the carbonyl group is bonded to two hydrocarbon radicals are ketones; the general formula is CₙH₂ₙO (n ≥ 3), so they are interclass isomers of aldehydes with the same carbon number: C₃H₆O — propanal CH₃CH₂CHO and propanone CH₃COCH₃. The rational name consists of the radicals plus “ketone” (dimethyl ketone, methyl ethyl ketone), the systematic name is the alkane name plus “-one” with the number of C=O: propanone, butanone, pentanone-2. Preparation: oxidizing secondary alcohols (CH₃–CH(OH)–CH₃ + CuO → CH₃–CO–CH₃ + Cu + H₂O), hydrating alkynes other than acetylene (CH₃–C≡CH + H₂O → CH₃–CO–CH₃), hydrolyzing 2,2-dihaloalkanes. Ketones are reduced by hydrogen to secondary alcohols: CH₃COCH₃ + H₂ → CH₃CH(OH)CH₃. Unlike aldehydes they do not give the silver mirror and do not reduce Cu(OH)₂; only strong oxidants such as KMnO₄ or K₂Cr₂O₇ oxidize them, with breaking of the chain. Acetone is a colourless volatile liquid with a characteristic smell (b.p. 56 °C), highly flammable, miscible with water in any ratio, and a solvent for paints and lacquers; breathing much of its vapour or using it near a flame is dangerous.

Worked examples
Ketones of C₅H₁₀O: pentanone-2, pentanone-3, 3-methylbutanone-2 (3). Oxidizing propanol-2 (60 g/mol) gives acetone (58 g/mol): 60 g of alcohol gives 58 g of acetone.
Hydrogenating acetone gives propanol-2: 58 g of acetone + 2 g of H₂ → 60 g of propanol-2. Propyne + water → acetone: hydrating propyne, unlike acetylene, gives a ketone, not an aldehyde.
Class activity

Make a table comparing acetone and ethanal: formula, functional group, silver mirror (yes/no), reduction product. Acetone is highly flammable: never use it near a flame; nothing is used in class.

Practice
1
What are the functional group and general formula of ketones?
2
How many ketones fit C₅H₁₀O?
3
How many grams of acetone form when 120 g of propanol-2 (M = 60) are fully oxidized (M(acetone) = 58)?
4
Why does acetone not give the silver mirror reaction?