Organic Review [39 marks]

B
1. How many structural isomers of C6H14 exist? [1 mark]
A. 4
C C C C C C
B. 5
d
C. 6
c É c c c
D. 7
c É c
i
c
c c c
2. What is the order of increasing boiling point?
d [1 mark]
B A. C4H10 < CH3COOH < CH3CH2CHO < CH3CH2CH2OH i i
B.
C.
C4H10 < CH3CH2CHO < CH3CH2CH2OH < CH3COOH
CH3COOH < CH3CH2CH2OH< CH3CH2CHO < C4H10
I É ll
D. C4H10 < CH3CH2CH2OH < CH3CH2CHO < CH3COOH I I dO H

3. What are the functional groups in the aspirin molecule?

i i E [1 mark]

I. Ether R O R
II. Carboxyl
CEO H
Éo
III. Ester
R
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
C 4. Which molecule has a tertiary nitrogen?
A. (CH3)2NH
[1 mark]

B. (C2H5)4N+I−
C. C3H7N(CH3)2
D. C6H5NH2

5. Which functional group is present in paracetamol? [1 mark]

A. Carboxyl
B. Amino
C.
D.
Nitrile
Hydroxyl Y
6. The structure of a drug used to treat symptoms of Alzheimer’s disease is [1 mark]

C shown below. Which functional groups are present in this molecule?

A. Hydroxyl and ester

X
B. Hydroxide and ether
C. Hydroxyl and ether
D. Hydroxide and ester
y
 7. Which alcohols are oxidized by acidified potassium dichromate(VI) [1 mark]
A solution when heated?

A. I and II only
B. I and III only
C. II and III only
D. I, II and III

8. What is the name of the alkane shown in the diagram below, applying [1 mark]

D IUPAC rules?

i c d d
I
A. Hexane
B. 1,1,1-trimethylpropane
C. Ethylmethylpropane
D. 2,2-dimethylbutane

D9. What is the major product of the reaction between HCl and but-2-ene?
A. 1,2-dichlorobutane
[1 mark]

B. 2,3-dichlorobutane
C. 1-chlorobutane
D. 2-chlorobutane i i i
a
Hi
B
10. Which compound can be oxidized when heated with an acidified solution [1 mark]
of potassium dichromate(VI)?
A. CH3C(O)CH2CH3
B. CH3CH2CH(OH)CH 3
C. (CH3)3COH
D. CH3(CH2)2COOH

11. Which conditions are used to convert ethanol to ethanal? [1 mark]

D A.
B.
Excess oxidizing agent and reflux
Excess oxidizing agent and distillation
C. Excess ethanol and reflux
D. Excess ethanol and distillation

12. Which compound can both be esterified and turn acidified potassium [1 mark]
C dichromate(VI) solution green?
A. (CH3)3COH
B. CH3CH2CO2H
C. (CH3)2CHOH
D. CH3CH2COCH3

13. Which compound could be X in the two-stage reaction pathway? [1 mark]

C C2 H4 → X → C2 H5 OH
A. C2 H6
B. C2 H3 OH
C. C2 H5 Br
D. C2 H4 Cl2

14. Which statements are correct for the reaction of ethene with bromine in [1 mark]
D the absence of ultraviolet light?
I. It is an addition reaction.
II. The organic product is colourless.
III. The organic product is saturated.
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
 Benzene is an aromatic hydrocarbon.

15a. Discuss the physical evidence for the structure of benzene. [2 marks]

have the same strength and length C C bonds

only one isomer exists for 1,2 dibromobenzene

15b. State the typical reactions that benzene and cyclohexene undergo with [1 mark]
bromine.

electrophilic substitution

electrophilic addition
 The photochemical chlorination of methane can occur at low temperature.

16a. Using relevant equations, show the initiation and the propagation steps [3 marks]
for this reaction.

12 Cl Cl

Cl City Cl H [Link]
Cla [Link] Cl CH t Cl

16b. Bromine was added to hexane, hex-1-ene and benzene. Identify the [1 mark]
compound(s) which will react with bromine in a well-lit laboratory.

hexane

16c. Polyvinyl chloride (PVC) is a polymer with the following structure. [1 mark]

State the structural formula for the monomer of PVC.

H
T
c L
H H
 Alkenes are widely used in the production of polymers. The compound A, shown
below, is used in the manufacture of synthetic rubber.

I É i

17a. (i) State the name, applying IUPAC rules, of compound A. [3 marks]
(ii) Draw a section, showing three repeating units, of the polymer that can be
formed from compound A.
(iii) Compound A is flammable. Formulate the equation for its complete
combustion.

i 2 methlyprop l ene

ii

t it
17b. Compound B is related to compound A. [5 marks]

(i) State the term that is used to describe molecules that are related to each other
in the same way as compound A and compound B.
isomer
(ii) Suggest a chemical test to distinguish between compound A and compound B,
giving the observation you would expect for each.
Test:
Observation with A: colorless
Observation with B:
brown
(iii) Spectroscopic methods could also be used to distinguish between compounds
A and B.
1
 Predict one difference in the IR spectra and one difference in the 1H NMR spectra
of these compounds, using sections 26 and 27 of the data booklet.
IR spectra:
1H NMR spectra:

17c. A sample of compound A was prepared in which the 12C in the CH2 [3 marks]
group was replaced by 13C.
(i) State the main difference between the mass spectrum of this sample and that
of normal compound A.
(ii) State the structure of the nucleus and the orbital diagram of 13C in its ground
state.
 17d. Draw a 1s atomic orbital and a 2p atomic orbital. [1 mark]

A 18. Propene reacts separately with H 2O/H+ and H2/Ni to give products X and [1 mark]
Z respectively.

What are the major products of the reactions?

19. In which order should the reagents be used to convert benzene into [1 mark]
C phenylamine (aniline)?

20. What is the correct order for the increasing rate of hydrolysis of [1 mark]
c halogenoalkanes by dilute aqueous sodium hydroxide?
A. CH3 CH(CH3 )CH2 Cl < CH3 CHClCH2 CH3 < (CH3 )3 CCl < (CH3 )3 CBr
B. (CH3 )3 CBr < (CH3 )3 CCl < CH3 CHClCH2 CH3 < CH3 CH(CH3 )CH2 Cl
C. (CH3 )3 CCl < (CH3 )3 CBr < CH3 CHClCH2 CH3 < CH3 CH(CH3 )CH2 Cl
D. CH3 CHClCH2 CH3 < CH3 CH(CH3 )CH2 Cl < (CH3 )3 CBr < (CH3 )3 CCl
A
21. What is the major organic product formed from the reaction of (CH3 )3 CBr [1 mark]
with a concentrated, ethanolic solution of KOH?
A. (CH3 )3 COH
B. (CH3 )2 CCH2
C. (CH3 )2 CO
D. (CH3 )2 CHO

22. 1-bromobutane, CH3 CH2 CH2 CH2 Br, can be converted to 1- [1 mark]
C aminopentane, CH3 CH2 CH2 CH2 CH2 NH2 , in a two-step process.
I
CH3 CH2 CH2 CH2 Br → CH3 CH2 CH2 CH2 CN
II
CH3 CH2 CH2 CH2 CN −→ CH3 CH2 CH2 CH2 CH2 NH2
What are the reagents I and II?

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