Tutorial 2 Carbonyl Compounds

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TUTORIAL 2: CARBONYL COMPOUNDS (ALDEYDE AND KETONE)

1. Write the IUPAC names for these carbonyl compounds.


a) CH3CH(CH3)CH(Cl)CH2CH2CHO

b) CH3-CH2-CH2-CH=CH-CHO

c) O O
CH3 C CH2 CH2 CH2 C H

d)

O
e)
O

O
f)
O

g)
O

h)

CHO
2. Draw the structural formula for the following organic compounds.
a) 4-methyl-4-pentenal
b) cis-3-tert-butylcyclohexanecarbaldehyde
c) 3,5-dinitrobenzaldehyde
d) 1-chloro-2-hydroxy-3-hexanone
e) 4-heptene-2-one
f) phenyl propyl ketone

3. Give the products formed when propanal and propanone reacts with following
reagents:
a) NaBH4
b) K2Cr2O7/H2SO4
c) 2,4-dinitrophenylhydrazine
d) CH3CH2MgBr, then H3O+

COMPILATION OF QUESTIONS FROM PAST YEAR


JULY 2023
QUESTION 8

Compound O: Propanal
Compound P: Propanone
Compound Q: Benzaldehyde

Predict the expected observation for compound O, P and Q when treated with the following
chemical reagent.

a) Tollen’s reagent
(2 marks)

b) Fehling’s solution
(3 marks)
QUESTION 2

Consider the following reaction.

Compound X

Li+-AlH(O-t-Bu)3

PCC/ CH2Cl2 O
Compound W 2,4-DNP
H Compound Y

2-cyclohexyl ethanal

CH3MgBr

Compound Z

a) Illustrate the structural formula for compound W and X.


(2 marks)

b) Write the balanced chemical equation when 2-cyclohexyl ethanal produces compound Y.

(3 marks)

c) Nucleophilic addition reaction of 2-cyclohexyl ethanal produces compound Z. Outline a


stepwise mechanism for this reaction.
(5 marks)

FEBRUARY 2023
QUESTION 6

Consider the following compounds.

a) Give the IUPAC name for compound K and compound L.

(3 marks)

b) Predict the product formed when compound L reacts with acidic potassium permanganate.

(2 marks)
QUESTION 2

a) Outline the synthetic pathway to produce aniline from benzaldehyde.

(6 marks)

b) Compound T is a ketone with molecular formula of C5H10O can be prepared from oxidation
of 3-methyl-2-butanol. Compound T will react with hydrogen cyanide to produce compound
U. Compound U then reacts with water and yield compound V. In other reaction, compound
T undergoes condensation with hydrazine and produce compound W. Determine the
structural formula for compound T, U, V and W.
(4 marks)

JULY 2022
QUESTION 2

a) Suggest the structural formula for the following compounds.

i) Oct-4-ene-2-one
ii) 4-benzylcyclohexanecarbaldehyde
(3 marks)

b) Explain a chemical test to differentiate 2-propanone and propanal.


(2 marks)
QUESTION 1

Consider the following reaction scheme.

Compound Q

phenylhydrazine

O O O
Reagent I Reagent II
Cl H OH
3-methylbutanal

Zn/Hg, HCl
MgBr

Compound M
Compound N

a) Predict suitable reagents for Reagent I and II.


(2 marks)

b) Illustrate the chemical structures for compound M, N and Q.


(6 marks)

c) Sketch the product formed when 3-methylbutanal reacts with water.


(2 marks)
FEBRUARY 2022
QUESTION 2

a) Give the IUPAC name for compound A and B.


O
NO2
H

O
NO2

Compound A Compound B
(3 marks)

b) Suggest two chemical tests to differentiate propanal and 3-pentanone.


(2 marks)

QUESTION 1

Consider the following scheme

a) Illustrate the chemical structures for compound R, S and T.


(6 marks)

b) Predict the suitable reagents for X and Y.


(2 marks)

c) Show a stepwise mechanism for the conversion of compound Q to compound R.

(2 marks)
DECEMBER 2019
DECEMBER 2018
JUNE 2019
JUNE 2018
JAN 2018

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