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CHEMISTRY DEPATMENT
CH110 Tutorial Sheet 8 - Organic Chemistry

1. Give the IUPAC name of the following hydrocarbons:

a) CH3CH2C(CH3)2CH2CH2CH2CH3

b) i)

c)
j)

d)

k)

e)

j)

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 l)

m) p)

q)
n)

r)

o)

s)

2. For each of the substances in question 1, identify whether it is saturated or unsaturated.

3. Draw the structures of each of the following:

a) 2,3,5,6-tetramethyloctane.
b) cis-3,4-dimethyl-3-hexene
c) 1-ethyl-3-methylcycloheptane
d) 4,4-dimethyl-2-pentyne
e) 6-methyl-2,4-nonadiene
f) ethylcyclopentane
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 g) 2,3-dimethyl-1,3-butadience
h) trans-2-butene
i) 2,3,3-trimethyl-1-hexene
j) 2-tert-butylpentane
4. a) Draw four possible structures for the compounds with the formula C5H8
b) Why are such compounds called isomers?

5. Draw and name all the structural isomers of each of the following:
a) C5H12
b) C6H14
c) C7H16

6. Predict the products of the following reactions:

a) Pentane + O2
b) 2-methylpropane + Br2
c) 2,3-dimethylhexane + O2  
hv

d) 3-ethyl-5-methylheptane + Cl2 

hv

7. Reagents such as HCl, HBr, and HOH (H2O) can add across carbon–carbon double and
triple bonds, with H forming a bond to one of the carbon atoms in the multiple bond and
Cl, Br, or OH forming a bond to the other carbon atom in the multiple bond. In some
cases, two products are possible. For the major organic product, the addition occurs so
that the hydrogen atom in the reagent attaches to the carbon atom in the multiple bond
that already has the greater number of hydrogen atoms bonded to it.
a) What is the name of the ruled followed in this description?
b) With this rule in mind, draw the structure of the major products for each of the
following reactions:
𝑃𝑡
i) CH3CH2CH=CH2 + H2O →
ii) CH3CH2CH=CH2 + HBr →
iii) CH3CH2C≡CH + 2HBr →

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 iv)

H+

8. Using appropriate reactants, alcohols can be oxidized into aldehydes, ketones, and/or
carboxylic acids. Primary alcohols can be oxidized into aldehydes, which can then be
oxidized into carboxylic acids. Secondary alcohols can be oxidized into ketones, while
tertiary alcohols do not undergo this type of oxidation.
a) Draw the structure of the compound with three carbon atoms that belongs to each of
the following families of organic compounds:
i) Alcohols iv) Carboxylic acids
ii) Aldehydes v) Esters
iii) Ketones vi) Ammines
9. Give the structure of the product(s) resulting from the oxidation of each of the following
alcohols.
i) 3-methyl-1-butanol vi)
ii) 3-methyl-2-butanol
iii) 2-methyl-2-butanol
iv) Propanal
vii)
v) 2,3-dimethyl pentanal

10. The relationship between the following two structures is:

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(A) Enantiomers (B) diastereomers (C) structural isomers (D) identical (E) none of the above

11. Which of the following molecules is chiral?

12. Bromination of alkanes is a much slower reaction than chlorination. Which of the following
is expected to be the major organic product when 2-methylbutane is allowed to react with Br2
in the presence of light or heat?

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13. The major monobromination product in the following reaction is

14. Determine the relationship between the two molecules shown:

a. constitutional isomers
b. enantiomers
c. diastereomers
d. identical molecules

15. The hybridization of the central carbon in CH3C≡N and the bond angle CCN are
a. sp2, 180°.
b. sp, 180°.
c. sp2, 120°.
d. sp3, 109°.

16. Which of the following statements about an sp hybridized carbon is FALSE?

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a. It is divalent.
b. It forms bonds that are linear.
c. It has two p orbitals.
d. It always forms triple bonds to carbon.

17. Which molecule has the largest dipole moment?

a. HCl
b. CCl4
c. H2S
d. CO2

18. What are the hybridizations of carbons 1 and 2 respectively in the following structure?

a. sp3 and sp2

b. sp2 and sp3
c. sp3 and sp
d. sp2 and sp2

19. What are the hybridizations of atoms 1 and 2 respectively in the following structure?

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a. sp3 and sp2
b. sp2 and sp3
c. sp3 and sp
d. sp2and sp

20. Identify the orbital hybridization at the two indicated carbons in the molecule below

a. C1: sp; C2: sp

b. C1: sp2; C2: sp2
c. C1: sp; C2: sp2
d. C1: sp2; C2: sp

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21. The following compounds are used as indicators/dyes in most experiments in the
laboratory. State the hybridization of each carbon atom in each the following compounds:

Esterification (Preparation of Esters). The process of esterification involves the reaction of a

carboxylic acid with an alcohol in the presence of an acid catalyst. Water is also a product in
this reaction.

22. Complete the following esterification reaction:

a.

b.

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23. What carboxylic acid and alcohol are required to produce the following ester?

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