Download Year 13 Organic Chemistry Test

Year 13 Organic Revision Worksheet
QUESTION ONE
Name the following molecules using IUPAC systematic rules.
(a)
(b)
CH3-CHCl-CH3
O
CH3
CH2 C
NH2
(c)
_____________________________
CH3
_____________________________
H
C C
H
CH3
_____________________________
QUESTION TWO
Ethanol is found in alcoholic beverages and can be detected by a breathalyzer
test which uses acidified potassium dichromate.
(a)
Identify, by circling the correct word below, what type of alcohol
ethanol is.
primary
(b)
(d)
tertiary
quaternary
Acidified potassium dichromate is a weak oxidising agent in this
case, and will not produce a carboxylic acid from the alcohol. Circle
the correct organic product from the list below.
aldehyde
(c)
secondary
ketone
acyl chloride
amide
The organic product produced in (b) can then be identified by using
Tollen's reagent. What would be seen in a positive test with
Tollen's reagent?
_____________________________________________________
_____________________________________________________
A second alcohol, 2-methyl propan-2-ol, will not give a positive
breathalyzer test. Why not?
_____________________________________________________
_____________________________________________________
(e)
2-methyl propan-2-ol can be identified with Lucas' Reagent. What
is Lucas' Reagent and how is it used to identify tertiary alcohols?
_____________________________________________________
_____________________________________________________
(f)
Write a balanced chemical equation for the reaction of ethanol with
Lucas' Reagent.
_____________________________________________________
QUESTION FOUR
Fill in the gaps with the correct reactants, products or catalysts in the reactions
below. You may draw graphical (structural) formulae or constitutional formulae.
If there is more than one organic product, (e.g. due to Markovnikov’s rule), give
the major product only.
(a)
CH3
(b) CH3
CH CH2 + HCl
O
C
O H
+
CH3
Cl
(c)
C N CH3
+ HCl
O
CH3
CH2 C
H
+ H+/Cr2O72(organic product only)
OH
(d)
(e)
CH3
CH CH3
CH3
CH2 OH +
CH3
CH CH2
+ H2O
CH3CH2Cl + HCl + POCl3
QUESTION FIVE
Name the type of reaction shown in question four above:
Reaction (a) _______________________
Reaction (c) _______________________
Reaction (d) _______________________
QUESTION SIX
(a)
Draw a section of the addition polymer formed from cis-but-2-ene.
(b)
Polyesters can be formed by the reaction between carboxylic acids
and alcohols. Name the catalyst for this reaction.
______________________________________
(c)
Draw a section of the polymer formed when the two molecules
below react to form a polyester.
HOOC-CH2-COOH
(d)
+
HO-CH2-CH2-OH
What type of molecule could be used instead of a carboxylic acid to
remove the need for a catalyst?
_______________________________________
(1 mark)
QUESTION SEVEN
You are given a sample of ethanol and asked to produce ethanoyl chloride. You
have access to any chemical reagents and equipment that you need. How would
you do this? State all reaction conditions required and write equations for all
relevant reactions.