Tutorial 7 Chapter 7: Carbonyl Compounds: Chm207 (Organic Chemistry)

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CHM207 (ORGANIC CHEMISTRY )

TUTORIAL 7
CHAPTER 7: CARBONYL COMPOUNDS
1)

Name the following ketones and aldehydes.


a) CH3CO(CH2)4CH3
b) CH3(CH2)2CO(CH2)2CH3
c) CH3(CH2)5CHO
d)

O
C

e) CH3CH2CH2CHO
f) CH3CH2CHBrCH2CH(CH3)CHO
g)

O
CH3

h)

C CH2 CH3

i)

CH3 C CH2 CH2 CH2 C H

j)

2)

CH3-CH2-CH2-CH=CH-CHO

Draw the structures for the following compounds:


a) 4-methyl-3-pentanone
b) isobutyl methyl ketone
c) hepta-4-one
d) 4-methyl-4-pentenal
e) 2-hydroxypentanal
f) 4-methylcyclohexanone
1

CHM207 (ORGANIC CHEMISTRY )

3)

Arrange the following compounds in order of increasing boiling point.


a) ethanal, propane, ethanol, 1-propanol
b) 2-propanone, 2-butanone, 1-butanol, butane-1,2-diol

4)

Give the products formed when ethanal reacts with following reagents:
i) NaBH4
ii) K2Cr2O7/H2SO4
iii)LiAlH4
iv) HCN
v) 2,4-dinitrophenylhydrazine
vi) KMnO4 / H+ / heat
vii)Ag(NH3)2 / OHviii) NaOH / I2

5)

Predict the products formed when cyclohexanone reacts with reagents in


question (4) above.

6)

Give the reagents for the reactions below:


a)

OH

O
from

b)

O
CH3

c)

from

O
CH3CH2CH2 C OH

d)

CH3CH(OH)CH2CH3

O
from CH3CH2CH2 C H
O
from CH3CCH2CH3

CHM207 (ORGANIC CHEMISTRY )

7)

How you distinguish each of the following compounds by using chemical


test?
a) acetaldehyde and acetone (propanone)
b) phenyl methyl ketone and ethyl phenyl ketone
c) propanal and 1-propanol
d) 2-butene and 2-butanone

8)

Compound A with molecular formula C5H10O give the reactions as below:


a) A + 2,4-DNP : POSITIVE
b) A + Tollens Reagent: NEGATIVE
c) A + NaBH4 give compound B
d) B + CH3COOH
e) B

H+

H+

C + H2O

alkenes (2 products) (C5H10)

Compound A give positive results in iodoform test. Give the structures for
compound A, B, C and alkenes.
9)

A reaction sequence is shown below.

SOCl2
CH3CH2OH
pyridine

HCN/KCN

H3O+

LiAlH4
R

Draw the structures of the products P, Q, R and S.

10)

Show how to convert each of the following products using a suitable


reagents and condition.
a)
butanone to 2-butene
b)
chloroethane to ethanoic acid
c)
ethanol to 2-hydroxypropanoic acid.

11)

The ozonolysis of an alkene P gives CH3CH2CHO and HCHO. Draw the


structure of P and give name of the compound.

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