TUTORIAL 1

CHEMICAL BONDING

1. Complete the table below.

No molecular structural formula skeletal formula condensed formula

formula
H H
1
H C C H

H H

2 C4H10

3 HOCH2CH2COCH3

4 O

5 OH

6 CH3CH2COOH

7 C2H5CN

2. Determine the functional groups for compounds below.

a) d)

b) e)

c) f)

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

3. (a) Based on structure below:

b
2

1 c

3
a

(i) Determine the hybridization, bond angle, and geometry for (a), (b), and (c).
(ii) Determine number of σ bond and π bond for (1), (2), and (3).

4. Draw the resonance structure for the following compounds.

a) f)

b) g)

c) h)

d) i)

e) k)

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 2
STEREOCHEMISTRY

1. Draw all the possible structural isomers of:

a) C4 H10 b) C5 H10 c) C6 H12 d) C6 H14

2. a) Draw Sawhorse representation of ethane in:

i) staggered conformation
ii) eclipsed conformation
b) Draw Newman projection of propane in:
i) staggered conformation
ii) eclipsed conformation
c) Draw Newman and Sawhorse projections of butane through C1-C2 bond in
staggered conformation
d) Draw Newman and Sawhorse projections of butane through C2-C3 bond in
eclipsed conformation
e) Draw the most stable conformation of butane in Newman projection.
f) Draw the least stable conformation of butane in Sawhorse projection.

3. Classify each compound as a cis isomer, a trans isomer, or neither.

a) b) c)

4. In each of these questions, decide whether the structure drawn is the E- or Z- isomer.

a) b) c)

5. Identify the chiral carbon atoms by an asterisk (*) in each of the following structures. If no chiral
carbons are present, write achiral.

a) b) c)

d) e)

6. For each of the following compounds;

a) b) c)

i) Draw the mirror image

ii) Assign R or S configurations
iii) Draw the Fisher projections

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 3
ALKANES & ALKYL HALIDES

1. Draw the structural formula for the following:

a) 2-methylnonane
b) 4-ethyloctane
c) 3,3-dimethylpentane
d) 3-ethyl-2-methylpentane
e) 2-ethyl-1,1,3,3-tetramethylcyclopentane
f) isopropylcyclohexane
g) tert-butylcyclopentane
h) sec-butylcylobutane
i) 3-ethyl-1,1-dimethylcyclohexane

2. Give the IUPAC name of the following compounds:

a) b) c)

d) e) f)

g) h) i)

j) k) l)

3. Predict the reagent/product of each of the following reactions.

+ Zn/CH3COOH →
a) X

b) X Y

c) + X

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

4. Give one example of primary, secondary and tertiary alkyl halide.

5. Draw the structural formula of the following compounds.

a) 2-bromopentane
b) 5-chloro-2-iodoheptane
c) 2-fluoro-5-methylheptane
d) 1,3-dichloro-2-methylpropane
e) bromocyclopentane
f) 6-bromo-1-chloro-3-methylcyclohexane
g) 2-chloro-3,3-dimethylpentane
h) 1,1-dichloro-4-isopropylcyclohexane
i) 3-bromo-3-ethylhexane
6. Give the IUPAC name of the following compounds.

a) b)

c) d)

e) f)

g) h) i)

7. Predict the reagent/product of each of the following reactions.

a) X

b)
X

c) X

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 4
ALCOHOLS & ETHERS

1. Draw the structural formula of the following compounds and indicate whether the alcohol is primary,
secondary, or tertiary.

a) 3,3-dimethyl-1-butanol e) Cyclopropanol
b) 4-neopentylcyclohexanol f) 2-bromo-4-cyclopentanol
c) 2-ethyl-1-pentanol g) 1,3-cyclohexadiol
d) 3-bromo-2,3-dimethyl-2-pentanol h) 1,2,3-propanetriol

2. Give the IUPAC name of the following compounds.

a) b) c) d)

e) f) g) h)

i) j)

3. Predict the reagent/product of each of the following reactions.

a) X

b) X

c) X Y

d) X Y

e) X

X
f)

g) X

NaBH4
h) X

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 i)
X

j) X (major) + Y (minor)

X
k)

X
l)

m)

X
n)

o)
X

p) X

4. Draw the structural formula of the following compounds.

a) Ethoxycyclohexane
b) 1-bromo-2-methoxycyclohexane
c) 2-methoxy-1-cyclohexanol
d) 1-ethoxy-4-methoxybutane
e) 3-ethoxyhexane
f) 3-bromo-1,1-dimethoxycyclopentane
g) methyl propyl ether
h) 1,3-dimethoxypropane

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

5. Give the IUPAC name of the following compounds.

a) b) c)

d) e) f)

g) h) i)

6. Predict the reagent/product of each of the following reactions.

a) X

b) X

c) X

X
d)

e) X + Y

f) X + Y

g) X

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 5
AMINES

1. Draw the structural formula of the following compounds and indicate whether the alcohol is primary,
secondary, or tertiary.

a) 3-hexanamine
b) 2-methyl-1-butanamine
c) Trimethylamine
d) N-ethylcyclohexylamine
e) 1,5-pentanediamine
f) 5-chloro-N-ethyl-N,3-dimethyl-1-pentanamine
g) Diisopropylamine
h) Dicyclopentylamine

2. Give the IUPAC name of the following compounds.

a) b) c) d)

e) f) g) h)

i) j) k)

3. Predict the reagent/product of each of the following reactions.

a) X

X
b)

c)
X

d) X

X
e)

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 6
ALKENES

1. Give the IUPAC name of the following compounds.

a) b)

c) d)

2. Draw the structural formula of the following compounds.

a) 3-Ethyl-2-pentene e) 4-Isopropyl-1-nonene
b) cis-3-Octene f) 1-Bromo-3-methylcyclohexene
c) (Z)-1,2-difluoro-cyclohexene g) 3,7,7-Trimethyl-4-octene
d) 1,2-Diethyl-cyclopentene h) (Z)-3-Methyl-2-hexene

3. Give the cis, trans, (E) or (Z) naming of the following compounds.

Br C2H5 Cl Cl Br C2H5 Cl I
C C C C C C C C
C2H5 Br CH3 CH3 CH3 Cl CH3 CH3OH
(a) (b) (c) (d)

4. Give the structures of the products of the reactions of 3-methylpent-2-ene with each of the
following reagents.

(i) Br2/CCl4
(ii) HBr
(iii) H2SO4
(iv) KMnO4
(v) H2/Pt
(vi) O3, H2O (Zn)

5. Outline how the following compounds can be synthesised.

(i)
CH3CH2CH2CH2OH CH3CH2CH CH2
(ii)
CH3CH2CH2CH3 CH3CH2CH CH2
(iii) CH3CH2CH CH2
CH3CH2CH2CH2Br
(iv)
CH3CH2CHBrCH2Br CH3CH2CH CH2

O
(v)
CH3CH CH2 CH3 C
H
(vi) CH3CH CH2 CH3CH2CH2OH
(vii) CH3CH CH2 CH3CH(OH)CH3
(ix) CH3CH CH2 CH3CH(OH)CH2OH

SKO1013 Introduction to Organic Chemistry Sem 1_2018/2019

 TUTORIAL 7
ALKYNES

1. Give the IUPAC name of the following compounds.

a) b)

c) d)

2. Draw the structural formula of the following compounds

a) 3,3-dimethyl-1-butyne
b) 4,4,5 – trimethyl-2-hexyne
c) 3,4,6-triethyl-5,7-dimethyl-1-nonyne
d) trans-2,2,4-trimethyl-5-propyl- 3-octene

3. Give the names and the structures of the products the reactions of 1-butyne with the
following reagents.

(i) 1 mole H2/Ni

(ii) 2 moles H2/Ni
(iii) 1 mole Br2/CCl4
(iv) 2 moles Br2/CCl4
(v) 1 mol HCl
(vi) 2 moles HCl
(vii) 1 mol HBr/H2O2
(viii) 2 moles HBr/H2O2
(ix) KMnO4, (acidic and heat)
(x) NaNH2, NH3

4. Suggest the synthesis of the following compounds.

(i)
CH3C CH CH3C CCH2C(CH3)3
(ii)
CH3C CH CH3CCH3
O
(iii)
CH3CH2CH2Br CH3C CH
(iv)
CH3CHBrCH2Br CH3C CH

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 8
ALDEHYDES & KETONES

1. Give the IUPAC name of the following compounds.

a) e)

b) f)

c) g)

d) h)

2. Draw the structural formula of the following compounds

a) 3-ethyl-2-pentanone
b) 2,4,6-trimethylheptanal
c) 3-ethylcyclopentanone
d) 4-chloro-2-phenylpentanal
e) 4-methyl-2-pentanone
f) 3,3-dimethylcycloheptanone
g) 3-chlorocyclopropanone
h) 3-cyclopentyl-4-methylhexanal

3. Give a chemical test to differentiate between aldehydes and ketones.

4. Please complete the following reactions by either providing the reactants, products or
starting materials.

L
H H2SO4
B G
KMnO4
H2O, H+ B2H6,
OH
O H2O2
NaCN, HCl C
A H2SO4
H D
Zn (Hg) O3,
HCl, H2O H2Cr2O7 Zn,
LiAlH44 H3O+
K I E+F
J

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 9
CARBOXYLIC ACIDS & DERIVATIVES

1. Give the IUPAC name of the following compounds.

a) e)

b) f)

c) g)

d) h)

2. Draw the structural formula of the following compounds

a) 2-methylpropanoic acid f) butanadioic acid

b) 2,2,5-trimethylhexanoic acid g) 1,2-Dibromocyclopentanecarboxylic acid
c) 2-bromo-benzoic acid h) 3-Fluoropentanoic acid
d) 3-phenyl-2-propenoic acid i) 4-isopropyl-2,4-heptadienoic acid
e) 2-isobutyl-5,5-dimethylhexanoic acid

3. Please complete the following reactions by either providing the reactants, products or
starting materials.

P
I L M
KOH PCl3 HBr
KMnO4 Cu, CrO3 H2SO4 O3, Zn, H3O+
Br
A B J K N+O

KMnO4
F

E O H+ / H2O NaCN
BrMg
D C
HO
Q
LiAlH44 OH LiAlH44

NaOH
S
G H
R
H2, Pt

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

4. Please complete the following reactions.

5. Give the IUPAC name of the following compounds.

a) g)
O

N
b) h)
O

Cl
c) i)
O O O

d) O j) O

e) k)

f) l)

6. Draw the structural formula of the following compounds

a) 3-bromobutanamide g) benzoyl chloride

b) 3-chlorobenzamide h) 2-ethylpentanoyl chloride
c) N,N-dimethylpentanamide i) 3-bromo-2-ethylbutanoyl fluoride
d) methyl pentanoate j) ethanoic propanoic anhydride
e) ethylhexanoate k) pentanoic anhydride
f) Methyl benzoate l) benzoic butanoic anhydride

7. Please complete the following reactions by either providing the reactants, products or
starting materials.

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 C + D
R + S LiAlH4

H O
N H2O N
B H
E + F
Q
J OH DIBAH
O
LiAlH4 NH2 A O
P O
Cl OH
G + H
O OH

LiAlH4
ONa
K I

N H2O

L + M

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

 TUTORIAL 10
BENZENE AND DERIVATIVES

1. Give the IUPAC name of the following compounds.

a) h) o)

b) i) NO2 p)

c) j) q)

d) k) r)

e) l) s)

f) m) t)

g) n)

2. Draw the structural formula of the following compounds

a) 3-chloro-2-nitroaniline e) o-Bromotoluene
b) 2-bromo-4-chlorotoluene f) o-Nitrobenzaldehyde
c) 1-iodo-2,4-dinitrobenzene g) m-Nitrobenzoic acid
d) 1-bromo-2-ethylbenzene h) 2-fluoro-4-chlorotoluene

SKO3013_Basic Organic Chemistry Sem 1_2018/2019

3. Give the products of the following reactions with benzene, followed by (the products) reaction
with HNO3/H2SO4.

a) HNO3/H2SO4
b) SO3/H2SO4
c) Br2/FeBr3
d) CH3CH2Cl/AlCl3
e) PhCOCl/AlCl3 (Ph = phenyl)

4. Starting from benzene, propose efficient synthetic routes (multiple steps) for transformations
shown below. For each synthesis, clearly indicate the reagent used.

a)

b) O2N
OH

Cl

c)
HO OH

O O

SKO3013_Basic Organic Chemistry Sem 1_2018/2019