Isomerism, Alkanes, Alkenes

Isomerism, Alkanes and Alkenes

Question 1

(i) State the terms chain isomerism, positional isomerism and functional group isomerism.
(ii)State the type of isomerism in the following compounds

Compound A Compound B

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

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Question 2

(i) Explain how geometric isomerism arises in organic compounds.

(ii) State which compounds below exhibit geometric isomerism. State whether the particular
compound drawn is this cis or trans configuration.

Compound A Compound B

Compound C Compound D

Compound E Compound F

Compound G Compound H

Question 3

(i) Explain how optical isomerism arises in organic compounds.

(ii) State which compounds below exhibit optical isomerism. Draw the mirror images of the
enantiomers for compound D.

Compound A Compound B Compound C

Compound D Compound E Compound F

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Question 4

State the total number of stereoisomers for the compounds below. In addition, state the total
number of , and sp hybridized carbons.

Compound A Compound B

Question 5

Explain why alkanes such as ethane are chemically inert while alkenes are able to react with
reagents such as bromine.

Question 6

When propane reacts with chlorine, a mixture of products is obtained. Only a flash of UV light is
required to start the reaction.

(i) Give the structural formula of the isomers formed, assuming that only monochlorinated
isomers are formed.

(ii) Estimate the ratios of the isomers formed in (i), giving a reason for your answer.

(iii) An alkane, 2,3-dimethylbutane is isolated from the mixture of products above. Describe the
mechanism for this reaction to show the formation of 2,3-dimethylbutane.

(iv) Explain the need for UV light.

(v) Explain why only a flash of UV light is required.

A student suggested the free radical substitution followed the following step.

(vi) State if you agree with his suggestion. Explain your reasoning.

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Question 7

Alkenes can be prepared in the laboratory by using the apparatus shown below.

(a)(i) Give the structural formula of alcohol Q that can be used to prepare but-2-ene.

(a)(ii) Write a balanced chemical equation for the reaction in (a)(i).

(b)(i) Give the chemical formula of R.

(b)(ii) Explain why R must be heated strongly.

(c) At the end of the reaction, when no more but-2-ene is produced, the apparatus is left to cool
with the delivery tube out of the water. Suggest why this is done.

Question 8

Long chain alkanes undergo cracking to produce a possible mixture of smaller alkanes, alkenes
and hydrogen gas.

Alkane Q, , undergoes cracking to produce only 3 compounds A, B, and C in a ratio of 1 : 1 :

2.

A is found to have a molecular formula of . When A was mixed with chlorine and UV light,
only one monochlorinated product was formed.

When 10 of B is sparked in excess oxygen, there was a contraction of 30 . Upon

vigorous shaking with aqueous sodium hydroxide, there was a further contraction of 40 . All
volume measurements were made at room temperature and pressure. B exists as a pair of cis-
trans isomers.

(i) Determine the molecular formula of B from the volume measurements given above.

(ii) Determine the molecular formula of C from the information given and your answer in (i).

(iii) Hence, write the balanced chemical equation for cracking of Q.

(iv) Give the structural formulae of A, B and C.

(v) F, is an isomer of B. F does not decolourise aqueous bromine and forms three mono-
chlorinated isomers when mixed with limited chlorine and UV light. Give the full structural
formula of F.

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Question 9

(i) Identify the reagents and conditions for all the steps I to IX above. Give two possible
alternatives for Step V.

(ii) Explain how you would distinguish between butane and but-1-ene.

Question 10

(i) Identify the reagents and conditions required for Steps I, II and III. Give the structural
formulae for the compounds A to G.

(ii) Give the organic products formed when Z is heated with alkaline under reflux.

(iii) B can also be obtained from F. Suggest reagents and conditions for this conversion. Explain
why this preparation is not suitable.

(iv) Describe the mechanism of the formation of compound D from Y. Include the minor product
from this reaction and explain why D is the major product.

(v) Give the structural formula of the other product in Step I. State whether this product is the
major or minor product, giving a reason.

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Question 11

3,4-dimethylhexane, has molecular formula , undergoes free radical substitution.

(a)(i) Assuming only monochlorinated products are formed, give the structural formula of all
possible products formed. Suggest the ratios of for the products formed.

(a)(ii) Explain why free radical substitution creates different ratios for its products.

(a)(iii) The experimentally determined ratios for the products formed is different. Suggest
which product in (a)(i) will have a higher ratio than expected.

(a)(iv) The presence of nitrogen dioxide will slow the reaction. Explain this observation.

(b) Explain why the propagation and termination steps are fast while the initiation step is slow.

(c)(i) 3,4-dimethylhexane has two chiral centres. However, it is found to be optically inactive.
Suggest an explanation for this.

(c)(ii) Draw two isomers of which has one chiral centre and has six carbon atoms in its
longest chain.

(c)(iii) Draw an isomer of which has one chiral centre and has five carbon atoms in its
longest chain.

(c)(iv) Draw an isomer of which reacts with bromine to give only one mono-brominated
product.

(c)(v) Draw an isomer of which reacts with bromine to give three mono-brominated
products.

Question 12

(i) Give the reagents and conditions for steps I and II and the structural formulae for A and B.

(ii) In Step III, a 1 : 1 ratio of two isomeric products are formed. Account for this observation.

(iii) Why must the reaction in Step III occur under anhydrous conditions?

(iv) C is found to have a molecular formula of . Give the structural formula of C.

(v) Account for the formation of C by giving the mechanism in Step IV, showing clearly the
movement of electrons, partial charges and lone pairs.

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Question 13

Explain how you would distinguish the following compounds, giving the reagents and
conditions used and the observations seen for each compound.

(i) But-1-ene Butane

(ii) But-1-ene But-2-ene

(iii)

(iv) Hex-2,4-diene Hex-3-ene

Question 14

Suggest reagents and conditions for each step (no more than three steps) and draw the
structural formulae of the intermediates formed.

(i) to
(ii) to

(iii) to

(iv) to

(v) to

(vi) to

(vii) to

(viii) to