Doc Brown's Chemistry  Revising Organic Chemistry

 The molecular structure and naming of ALDEHYDES and KETONES - including nomenclature of some isomers

Revision notes for GCE Advanced Subsidiary Level AS Advanced Level A2 IB Revise AQA GCE Chemistry OCR GCE Chemistry Edexcel GCE Chemistry Salters Chemistry CIE Chemistry revising courses for pre-university students (equal to US grade 11 and grade 12 and Honours/honors level courses)

Examples of displayed formula of aldehydes and ketones, graphic formula, molecular formula, skeletal formula, structural formula of this homologous series

Summary of Organic Functional Groups * Notes * Quiz

summary of organic chemistry id tests

Structure & Naming of Alcohols & Ethers notes and quizzes

Structure & naming of carboxylic acids-derivatives & quiz

Naming aldehydes or ketones QUIZ: multiple choice or type in name quiz

and (iii) notes on comparing alcohol and phenol structures and

  oxidation sequence: alcohol ==> aldehyde/ketone ==> carboxylic acid

• Aldehydes and ketones are a group of compounds containing the carbonyl group, C=O.
• Aldehydes always have a hydrogen atom attached to the carbon of the carbonyl group, so the functional group is -CHO (see diagram). The functional group is shown by using 'al' in the suffix part of the name e.g. methanal, ethanal, propanal etc.
• Ketones always have two carbon atoms attached to the carbon atom of the carbonyl group, so the functional group is C-CO-C (see diagram). The functional group is shown by using 'one' in the suffix part of the name e.g. propanone, butanone, hexan-3-one etc.
• The substituent numbers are based on giving the C=O carbon the lowest number e.g. 2-methylbutanal ('al' position = 1). The number position of the C=O group in ketones needs to be specified for carbon chains of over 4, or less, if substituents present e.g. 3-methylbutan-2-one, heptan-2-one, heptan-3-one and heptan-4-one (there is no heptan-1-one, this is heptanal!).
• For the same 'carbon number', aldehydes and ketones are structural and functional group isomers based on e.g. for aliphatic carbonyl compounds C_nH_2nO.

• The shapes and bond angles of simple molecules - section on bond angles in organic molecules

1. methanal (formaldehyde), , ,

2. ethanal (acetaldehyde), , , ,

3. propanal (propionaldehyde), , , ,

4. 2-methylpropanal (2 not strictly needed but advisable, 2-methypropionaldehyde),

   • , ,

5. butanal (butyraldehyde), , ,

6. 2-methylbutanal (2-methylbutyraldehyde), ,

7. 3-methylbutanal (3-methylbutyraldehyde), ,

8. pentanal (old name 'valeraldehyde'), ,

9. benzaldehyde (benzenecarbaldehyde), and 2-hydroxybenzaldehyde

1. propanone (acetone, dimethyl ketone, DMK), , , ,

2. butanone (or butan-2-one, but 2 not strictly needed, methyl ethyl ketone, MEK, 2-butanone),

   • , , ,

3. 3-methylbutan-2-one (2 and 3 not strictly needed BUT advisable, 3-methyl-2-butanone),

   • ,

4. pentan-2-one (2-pentanone), , ,

5. pentan-3-one (3-pentanone), , ,

6. 1-phenylethanone

7. 2-hydroxyphenylethanone

Other examples of substituted ketones e.g. iodoketones

1. to 3., 5. to 6. and 10. are formed by the reaction of the parent ketone with iodine in the presence of an acid (e.g. HCl_(aq), because H⁺_(aq) catalyses the reaction)

1. iodopropanone (1-iodopropanone, 1- not really needed)

2. 1-iodobutanone (1-iodobutan-2-one, -2- not really needed, 1-iodo-2-butanone)

3. 3-iodobutanone (3-iodobutan-2-one, -2- not really needed, 3-iodo-2-butanone)

4. 4-iodobutanone (4-iodobutan-2-one, -2- not really needed, 4-iodo-2-butanone)

5. 1-iodopentan-2-one (-2- needed, 1-iodo-2-pentanone)

6. 3-iodopentan-2-one (-2- needed, 3-iodo-2-pentanone)

7. 4-iodopentan-2-one (-2- needed, 4-iodo-2-pentanone)

8. 5-iodopentan-2-one (-2- needed, 5-iodo-2-pentanone)

9. 1-iodopentan-3-one  (-3- needed, 1-iodo-3-pentanone)

10. 2-iodopentan-3-one (-3- needed, 2-iodo-3-pentanone)

11. Phenylketones e.g.

    • C₆H₅CH₃COCH₂CH₃  is 1-phenylbutan-2-one (1-phenyl-2-butanone)

    • CH₃COCH(C₆H₅)CH₃  is 3-phenylbutan-2-one (3-phenyl-2-butanone)

    • CH₃COCH₂CH₂C₆H₅  is 4-phenylbutan-2-one (4-phenyl-2-butaone)

12. ?

Alcohols can be readily oxidised to aldehydes and ketones and aldehydes are easily oxidised further to carboxylic acids. The reagent can potassium dichromate(VI) K₂Cr₂O₇ , acidified with diluted sulphuric acid H₂SO_4(aq) (colour change is orange to green).

However the oxidation products depend on the original structure of the alcohol. The alcohol functional group -OH in aliphatic alcohols is classified into primary, secondary and tertiary types (see below). When the -OH is attached directly to a benzene ring the molecule is called a phenol.

Primary aliphatic alcohols R-OH, R is H or alkyl: When oxidised they form aldehydes and then further oxidation gives a relatively stable carboxylic acid e.g.

1. ==>==>

   • ethanol ==> ethanal ==> ethanoic acid

2. ==>==>

   • 2-methylpropan-1-ol ==> 2-methylpropanal ==> 2-methylpropanoic acid

3.  ==> ==>

   • butan-1-ol ==> butanal ==> butanoic acid

4. ==>==>

   • pentan-1-ol ==> pentanal ==> pentanoic acid

Secondary aliphatic alcohols R-CH(OH)-R', R or R' are both alkyl (can be aryl): When oxidised they form relatively stable ketones (see NOTE below) e.g.

1.  ==> , propan-2-ol ==> propanone

2.  ==> , butan-2-ol ==> butanone (butan-2-one)

3.  ==> , pentan-3-ol ==> pentan-3-one

Tertiary aliphatic alcohols RR'R"C-OH, where R,R' or R" are all alkyl (or aryl): These are relatively stable to oxidation (see NOTE 1. further down) e.g.

1. 2-methylpropan-2-ol , or

2. 2-methylbutan-2-o l, or

3. 3-methylpentan-3-o l, or

1. Ketones and carboxylic acids are relatively stable to further oxidation because a strong C-C bond must be broken in the process. Prolonged oxidation with H₂SO_4(aq)/K₂Cr₂O₇ or using a more powerful oxidising agent, results in the formation of carbon dioxide, water and carboxylic acids of shorter carbon chain length than the original alcohol or ketone.

2. When a primary alcohol is oxidised to an aldehyde, the oxidation to the carboxylic acid is rapid. If the aldehyde formed first is the desired product, it must be immediately distilled off to prevent further oxidation.

Phenols ROH, R=aryl (i.e. the -OH group is directly attached to a benzene ring): Some are quite stable to oxidation, but others, like phenol itself, are quite readily oxidised to complex aromatic products. Examples of phenols …

1.  , , , phenol (for more Aromatic compounds)

2. 2-chlorophenol  (the phenol group is given position '1')

3. 3-methylphenol, and 2,5-dichloro-4-methylphenol

4.  , 2-hydroxybenzoic acid or 2-hydroxybenzenecarboxylic acid (it is both a phenol and a carboxylic acid BUT the -COOH group is 'higher ranking' so the phenol group is quoted as a substituent).

CH2O HCHO C2H4O CH3CHO C3H6O CH3CH2CHO CH3COCH3 C4H8O CH3CH2CH2CHO CH3COCH2CH3 C5H10O CH3CH2CH2CH2CHO CH3COCH2CH2CH3 CH3CH2COCH2CH3

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