11_Isomers_structure_formulae WS3 Total 30

Name_________________________

1. Predict the molecular formula of an alkane with 13 carbon atoms.

.......C13H28......................................................................................................................
.....
[Total 1 mark]

2. Draw the skeletal formula for 2-methylpentan-3-ol.

[Total 1 mark]

3. Cylcohexane and cyclohexene are both cyclic hydrocarbons.

H
H H
H H H
C C H
C C C C
H H H
H H H H
C C C C
C C
H H H H
H H H H

cyclohexane cyclohexene

(i) What is the molecular formula of

(ii) What is the empirical formula of cyclohexene? ....................CH2..........................

(iii) Calculate the percentage, by mass, of carbon in cyclohexene. Give your answer
to two significant figures.

answer .........................85.71%......................
[2]

4. Butan-2-ol and 2-methylpropan-2-ol are structural isomers.

Strathallan school 1
 (i) What is meant by the term structural isomer?

Structural isomers are molecules with the same molecular formula but have
different structural arrangements of atoms

[1]

(ii) Draw another structural isomer of these two alcohols.

[1]
[Total 2 marks]

5. Oil companies process hydrocarbons, such as octane, into branched and cyclic
hydrocarbons that promote efficient combustion in petrol.

Draw the skeletal formulae of a branched hydrocarbon and a cyclic hydrocarbon, each
containing eight carbon atoms.

[Total 2 marks]

6. In this question, you are asked to suggest structures for several organic compounds.

Compounds F, G and H are unbranched alkenes that are isomers, each with a relative
molecular mass of 70.0.

Compounds F and G are E/Z stereoisomers.

Compound H is a structural isomer of compounds F and G.

• Explain what is meant by the terms structural isomer and stereoisomer.

• Explain why some alkenes have E/Z isomerism.

• Analyse this information to suggest possible structures for compounds F, G and

Strathallan school 2
 In your answer you should make clear how each structure fits with the information
given above.

Structural isomers are molecules that have the same molecular formula but have
different structural arrangements of atoms, which causes them to have different
physical and chemical properties. Stereoisomer is another type of isomer, which have
the same molecular and structural formula but have but that differ in the special
arrangements of the same atoms. A type of stereoisomer is the E/Z isomers that only
form with alkenes because of the carbon=carbon double bond that restricts the rotation
about the planar C=C. The position of the groups bonded to the carbons in the double
bond cannot be interchanged, therefore different isomers are possible. With all the
information given I think a possible molecular formula is C5H10 because at least one of
the carbons has a double bond so a 1:2 ratio of carbon to hydrogen should be in the
formula and the relative atomic mas is 70 so with a little of trail and error you find it to
be C5H10. Now with the molecular formula I was able to figure out some possible
structure for F, G and H. For F and G some possible structures are cis-2-Pentene and
trans-2-pentene. For H the possible isomers are Pent-1-ene, Pent-2-ene, 2-Methyl-1-
butene, 3-Methyl-1-butene, and 2-Methyl-2-butene.
[Total 11 marks]

7. In this question, one mark is available for the quality of use and organisation of
scientific terms.

Name and give examples of the types of isomerism in compounds with formula C4H8.
Explain how each type of isomerism arises.

C4H8 has two position isomers, one cis/trans, one chain isomer, and two cyclic
isomers. So, there are six isomers in total. The position isomers are a type of structural
isomers, which this type of isomer is caused by the different positions of the same
functional groups around the structure. C4H8 can form the position isomers of But-1-
ene and But-2-ene. It can also form the cis/trans isomers, cis-But-2-ene and trans-But-
2-ene, which are a type of stereoisomer that is caused by the different arrangements of
groups attached to double bonded carbon atoms, which this restricts rotation and so
there’s two isomers possible. Chain isomers can also be formed which are a type of
structural isomer, the isomer formed is 2-Methylprop-1-ene. The last two isomers
possible are Cyclobutane and Methylcyclopropane, which are Cyclic isomers that are a
type of stereoisomers, which have no carbon double bonds and are cyclic molecules.

[8]
Quality of Written Communication [1]
[Total 9 marks]

Strathallan school 3