TUTORIAL 16: CARBONYL COMPOUNDS

16.1 Introduction to carbonyl compounds

At the end of the topic, students should be able to:
a) Give the general formula of aldehyde and ketones.
b) Draw the structures and name the carbonyl compounds for aldehyde and ketones (parent chain
C10) according to IUPAC nomenclature.
c) Explain the preparation of carbonyl compounds through:
i. Ozonolysis of alkene
ii. Friedel-Crafts acylation to produce aromatic ketone
iii. Oxidation alcohol.

1. Give the IUPAC name for each of the following aldehydes and ketones:
(a) CH3
CH3 CH2 CHC O
H
(b) Cl CH3
H3C C CH2 C C O
CH2 CH3 H H
(c) Br
CH3 CH CHC O
CH3 CH3
(d)
O

(e)
C O
CH3
(f)
CH2 C O
CH3

2. Draw the structural formula for each of the following compounds:

(a) 2-ethyl-3-methylpentanal
(b) 4-chloro-2-methyl-3-hexanone
(c) acetone
(d) acetaldehyde

3. Draw the structural formulae and give IUPAC names for

(a) seven isomeric carbonyls with the molecular formula of C5H10O.
(b) aldehydes and ketones with molecular formula of C8H8O containing a benzene
ring.

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16. 4 Chemical properties of carbonyl compounds

At the end of the topic, students should be able to:
a) Explain the chemical properties with reference to:
i. Nucleophilic addition with KCN/H+ or NaCN/H+, water, alcohol, sodium bisulphate, NaHSO3
and Grignard reagent.
ii. Reduction to alcohol using LiAlH4 followed by H3O+ or NaBH4 in methanol or H2/catalyst.
iii. Condensation reaction ammonia derivatives such as hydroxylamine, hydrazine,
phenylhydrazine and 2,3-dinitrophenylhydrazine(2,4-DNPH) as identification test for carbonyl
compounds.
iv. Oxidation with KMnO4/H+ or C2O72-/H+.
v. Explain the identification tests to differentiate aldehyde from ketone using Tollen’s, Fehlings’,
Benedict’s and Schiff’s reagent.
vi. Iodoform test to identify methyl carbonyl group CH3C=O

4. There are many similarities in the reactions of aldehydes and ketones with a wide
variety of reagents. However, they can be readily distinguished by the way they react
with oxidising agents. Suggest a chemical test to distinguish them.

5. Give a chemical test to distinguish between:

(a) benzaldehyde from benzyl alcohol
(b) hexanal from 2-hexanone
(c) 2-pentanone from 3-pentanone

6. Show how propanal can be synthesised from

(a) 1-propanol
(b) 3-hexene

7. Draw structural formula for the products formed when propanal reacts with
(a) NaBH4 in aqueous NaOH
(b) C6H5MgBr followed by hydrolysis

8. Compound X has the molecular formula of C5H10O. It does not react with Fehling’s
solution but can be reduced to an alcohol with LiAlH4. Draw all the possible
structural formula of X.

9. Show how the following conversions can be carried out:

(a) propanone to…
I. propene
II. 2-chloropropane
(b) cyclohexanone to cyclohexane-1,2-diol

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10. Complete the following reactions:

(a) CN
HCN
BA C OH
A

CH3
(b) CH3 CH3 H
BD
CH3 C CH2 CH2 OH A CH3 C CH2 C O
OH OH
(c) O
C2H5COCl
EC C C 2 H5
A

A
AlCl3
A

(d) O +
K2Cr 2O7, H
CH3 CH2 CH2 C H D
F
A

(e)
O + H2N NH NO2 E
G

O2N

11. Complete the following reaction scheme and write the structural formulae of A to E.
Specify the reagents I to III.
E

conc. H2SO 4

I
CH3 CH2 CH2 OH CH3 CH2 CH2 Br

[O]
O
i) LiAlH4 in ether i. CH3CH 2MgBr II
A CH3 CH2 CHO + B CH3 CH2 C CH2 CH3
ii) H3O+ ii. H2O, H
-
i. KMnO4, OH , 
III +
ii. H3O

CH 3OH, conc. H2SO 4

CH3 CH2 CH2 Cl C D


12. Propanone can be converted to various compounds as shown in the following reaction
scheme.

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i. CH3CH2MgBr O HCN H3O+

C A B
ii. H3O+ CH3 C CH3

i. LiAlH4 in ether
conc. H2SO4,  +
ii. H3O

D E
(major product)

(a) Draw the structural formulae of A, B, C, D and E.

(b) What is the rule used to predict the structure of D?
(c) One of the chemical tests that can distinguish D from E is by using Br2 in
CH2Cl2. State the observation and write the chemical equation.
(d) State the type of reaction involved in the formation of E.

13. Compounds W and X have the molecular formula of C8H8O. W reacts with hot
Fehling’s solution producing a red precipitate. X gives negative result towards
Fehling’s test but it reacts with LiAlH4 followed by hydrolysis to form alcohol Y.
Both X and Y react with iodine in NaOH solution to yield a yellow precipitate.
Determine the structural formulae of W, X and Y.
Give the products of the reactions between W and LiAlH4/H+, and acidified potassium
dichromate solution respectively.

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OBJECTIVE QUESTIONS

1. Acrolein has the following structural formula:

H2C CH CH
O
Which of the following is not true with regards to acrolein?
A. It does not exhibit stereoisomerism.
B. All the bond angles in the molecule are approximately 90.
C. It undergoes electrophilic and nucleophilic addition reactions.
D. It decolourises aqueous bromine and acidified potassium dichromate solution.

2. Choose the suitable Grignard reagent that can be used to prepare 2-methyl-3-pentanol
from propanal.
A. (CH3)3CMgBr
B. CH3CH2MgBr
C. (CH3)2CHMgBr
D. CH3CH2CH2MgBr

3. Butanal can be distinguished from butanone by using the following reagents EXCEPT
A. Schiff’s reagent
B. Tollens’ reagent
C. Iodoform test
D. Bromine water

4. Which of the following would attack the carbon atom in the carbonyl group?
A. Nucleophile
B. Electrophile
C. Free radical
D. Carbocation

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5. A compound P reacts with

 sodium hydroxide solution
 2,4-dinitrophenylhydrazine
 phosphorus(III) chloride
P could be
(a)
HO COCH 3

(b)
OCOCH 3

(c)
HOOC CH3

(d)
HO C CH2OH
O

Summary of options
A B C D
I only I and II only II and III only I, II, and III

6. 2-Hexanone and hexanal can be distinguished by

I. Brady’s reagent
II. Tollens’ reagent
III. Iodoform test

7. Compound Y gives an orange precipitate with 2,4-dinitrophenylhydrazine and shows

a positive iodoform test.
Y could be
I. Ethanal
II. Propanone
III. 2-Propanol

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