Core Organic Assessed Homework - 2

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Topic 6: Organic Chemistry I Assessed homework 2

Name: ……………………………………………………… Date due: ......................................

Part 1: MCQs [10 marks]

Where two marks are indicated the second mark will only be awarded for correct
working.

1. The best nomenclature for the geometry of the following compound is:

CH3
Me CH CH3

C C

Et CH 2 CH 2 CH3
A cis–
B trans–
C E–
D Z– [1 mark]

2. What is the IUPAC name of the following compound? [1 mark]

H CH 2Br

C C

F CH3
A (E)–3–bromo–1–fluoro–2–methylpropene
B (Z)–3–bromo–1–fluoro–2–methylpropene
C (E)–1–bromo–3–fluoro–2–methylpropene
D (Z)–1–bromo–3–fluoro–2–methylpropene

3. For which of the compounds below are cis–trans isomers possible? [1 mark]
CH3CH=CH2 CH3CH=CHCH2CH3 CH3CH=CHCH3
1 2 3
A only 2
B 1 and 2
C 2 and 3
D 1, 2 and 3
2
4. For which of the following alkenes is E–Z isomerism possible? [1 mark]
CH3CH2CH=CHCH2CH3 CH3CH2CH=CHBr
1 2

(CH3)2C=CHCH3 H2C=CHCH2CH(CH3)2
3 4
A 1 and 2
B 1 and 3
C 3 and 4
D 1, 2 and 3

5. Carbon–carbon double bonds do not freely rotate like carbon–carbon single bonds.
Why? [1 mark]
A The double bond is much stronger and thus more difficult to rotate.
B Overlap of the two 2p orbitals of the –bond would be lost.
C The shorter bond length of the double bond makes it more difficult for the
attached groups to pass each other.
D Overlap of the orbitals of the carbon–carbon -bond would be lost.

6. Which of the following is the correct prefix for the following diene? [1 mark]

H CH3

H 3C C C

C C CH2CH3

H H

A (2E,4E)–
B (2Z,4Z)–
C (2Z,4E)–
D (2E,4Z)–

7. How many isomeric alkenes with the formula C5H10 are possible. Include all
stereoisomers.? [2 marks]
A four
B five
C six
D seven

8. Compounds containing oxygen are sometimes added to hydrocarbon fuels to reduce


incomplete combustion and improve engine performance.
Which contains the greatest number of oxygen atoms? [2 marks]
3
(Relative molecular masses: CH3OH = 32, C2H5OH = 46, CH2OHCH2OH = 62, C4H9OH
= 74)
A 8.0 g of methanol, CH3OH
B 9.2 g of ethanol, C2H5OH
C 6.2 g of ethane-1,2-diol, CH2OHCH2OH
D 7.4 g of butan-1-ol, C4H9OH

Part 2 [30 marks]


1. (a) Petroleum contains a mixture of hydrocarbons. The mixture can be separated into
fractions by fractional distillation. These fractions contain saturated hydrocarbons
that belong to the homologous series of alkanes.
(i) State what is meant by the terms hydrocarbon and homologous. [2 marks]
(ii) On what physical property of compounds is the separation based? [1 mark]
(b) One of the fractions, naphtha, is cracked to give more useful substances. A typical
constituent of naphtha is decane, C10H22. Write two chemical equations for the
cracking of decane to show how propene and other alkanes are produced.
[2 marks]

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