CHM257 (ORGANIC CHEMISTRY 1)

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TUTORIAL 1
CHAPTER 1: INTRODUCTION TO ORGANIC CHEMISTRY
1) What kind of hybridization do you expect for each carbon atom in the following
molecules?

a) Acetic acid c) acrylonitrile



b) 3-buten-2-one d) butane
CH
3
CH
2
CH
2
CH
3


2) Draw a line-bond structure for propene, CH
3
CH=CH
2
; indicate the hybridization
of each carbon; and predict a value of each bond angle.
3) Predict the hybridization, geometry and bond angles for bold atom in
a) CH
3
CH=CHCH
3

b) CH
2
=NCH
3

c) HCOH
d) CH
3
C(CH
3
)
2
CH
2
CH
2
CH
3


4) Referring to the structure shown below:





a) Draw a complete Lewis structure by showing all valence electrons and any
positive or negative formal charge.
b) Identify the functional groups present in the structure.





C H
3
C
O
OH
C C CH
3
O
CH
2
H
C C
H
C N
H
H
NH
2
O
CHM257 (ORGANIC CHEMISTRY 1)
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5) Consider the following organic compound.




a) For each carbon atom labelled X and Y determine,
i) types of hybridization
ii) bond angle
iii) geometric form
b) Give two functional groups present in the above molecule.
c) How many sigma and pi bonds present in the above molecule.
d) Determine the molecular formula for this organic compound.
6) Draw a complete Lewis structure with formal charges for the following
compounds.
a) ammonia, NH
3

b) nitrate ion, NO
3
-

7) Draw resonance structure of these compounds:
a) NO
3
-
b) ClO
3
-
8) Classify the following species as free radical, electrophile or nucleophile.
a) Cl
2
f) NH
3

b) Br
-
g) HBr
c) Cl h) AlCl
3

d) H
2
O i) SiCl
4

e) CH
3
+
j) Cl
+

9) Define and give two examples of Lewis acids and Lewis bases.

CH
2
CH
O
HO
X Y
CHM257 (ORGANIC CHEMISTRY 1)
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10) Identify the Lewis acids and Lewis bases in the following reactions:
a) CH
3
OH + H
+
CH
3
OH
2
+

b) CH
3
OH + NH
2
-
CH
3
O
-
+ NH
3

c)

11) Draw all possible isomers for these following molecules:
a) C
4
H
8

b) C
3
H
5
Br
c) C
2
H
2
Br
2

12) For each of the following compounds, write the (i) expanded formula and (ii)
skeletal formula.
a) CH
3
CH
2
CH(OH)CH
2
CH
3

b) CH
3
CH(Cl)CH
2
CH
3

c) CH
3
CH
2
COOH
d) CH
3
CHCHCH(CH
2
CH
3
)CH
2
CH
2
CH
3

13) For each of the following molecules, identify the homologous series and the
functional group to which it belongs.
a) CH
3
CH=CH
2

b) CH
3
CH
2
COCH
3

c) CH
3
CH
2
COOH
d) CH
3
CH
2
CH
2
NH
2

e) CH
3
CH
2
COH

14) The structural formulae of some organic compounds are given below:
a) CH
3
CH(OH)CH
2
OH
b) C
2
H
5
CH(CH
3
)CH(NH
2
)CONH
2

c) CH
3
CH(Br)CH(CH
3
)CH
2
Br
Write the expanded formula for each of these molecules and mark the chiral
carbon or stereogenic centre in each of the molecule with an asterisk (*). Which
of the compounds are optically active?
CH
3
C
O
H ZnCl
2
CH
3
C
O
H
ZnCl
2
CHM257 (ORGANIC CHEMISTRY 1)
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15) Draw the structure for each molecule:
a) trans-4-octene, CH
3
CH
2
CH
2
CH=CHCH
2
CH
2
CH
3

b) cis-1,2-dichloropropene, CH(Cl)C(Cl)CH
3

c) trans-2-pentene, CH
3
CHCHCH
2
CH
3

d) cis-1,3-dimethylcyclohexane,