CHEM1002
•
2012-N-12
November 2012
Give the major organic product(s) from the following reactions. Pay particular attention
to the stereochemistry and/or the correct ionic from where relevant.
Marks
2
CHEM1002
•
2010-N-8
November 2010
Classify the starting materials for each of the following reactions as nucleophile or
electrophile in the boxes provided. Classify the products of the reactions as
primary (1o), secondary (2o), tertiary (3o) or quaternary (4o) in the boxes provided.
Marks
5
CHEM1002
2009-N-8
November 2009
• Give the name of the starting material where indicated and the constitutional formula
of the major organic product formed in each of the following reactions.
Na2Cr 2O7 / H
OH
COOH
Name: 3-methyl-1-butanol
Br
conc. KOH, ethanol
heat
Name: 1-bromobutane
Br
Br
N(CH3)3
N
Marks
5
CHEM1002
•
2009-N-9
November 2009
Marks
Consider the following reaction sequence.
6
C
CH3OH
O
O
OH
Cl
B
aqueous NaOH
excess
D
(CH3) 2NH
1. LiAlH4
2 equiv.
2. H3O
E + F
A
Give the reagent B and draw the constitutional formulas of the major organic
products, A, C, D, E and F, formed in these reactions.
A
D
O
OH
O
B
•
E
O
SOCl2
N
C
•
F
O
Cl
OCH3
H N H
CHEM1002
•
2008-N-9
November 2008
Marks
Consider the following reaction sequence.
6
COOCH3
dilute H2SO4
heat
SOCl2
A
Reagent D
CH2OH
B
Reagent C
CON(CH3)2
conc. H2SO4
E
heat
Reagent F
Give the reagents C, D and F and draw the structures of the major organic products,
A, B and E, formed in these reactions.
A
D
COOH
(1). LiAlH4 / dry ether
(2). H+ / H2O
(Reduction of carboxylic acid to
primary alcohol).
(Hydrolysis of an ester to a
carboxylic acid).
B
E
O
Cl
(Formation of an acid chloride from
a carboxylic acid).
(Acid catalysed elimination of H-OH
(“dehydration”) to form C=C).
ANSWER CONTINUES ON THE NEXT PAGE
CHEM1002
2008-N-9
November 2008
F
C
CH 3
H N
CH 3
(Formation of amide from acid
chloride).
H2 / Pd/C
(Reduction of alkene to alkane).
CHEM1002
•
2007-N-8
November 2007
Marks
6
Consider the following reaction sequence.
O
Br
OH / H2O
reagent B
OH
A
NaOH
reagent D
C
O
(CH3CH2)2NH
F
E
Cl
CH3OH
Give the reagents B and D and draw the structures of the major organic products,
A, C, E and F, formed in these reactions.
A
D
OH
B
SOCl2 / heat
E
O
Cr2O72– / H+
O
C
F
O
O
O
N
CH3OH
CHEM1002
•
2006-N-8
November 2006
Marks
6
Consider the following reaction sequence.
B
1) LiAlH4
2) H / H2O
O
OH
reagent A
NaOH
C
H
O
reagent D
E
excess
H2NCH 3
Cl
CH3OH
F
O
Give the reagents A and D and draw the structures of the major organic products,
B, C, E and F, formed in these reactions.
A
D
Cr2O72- / H+
SOCl2
B
E
O
OH
CH3
N
H
C
F
O
O
CH3
O
O
CHEM1002
2005-N-8
November 2005
 Classify the starting materials of the following reactions as nucleophile or electrophile
and indicate with  and  the polarisation of the C–Br and C=O bonds.
CH3
H3C N
δ
Br
+
CH3
δ+
CH3
H3C N CH3
Br
electrophile
nucleophile
H
nucleophile
+
H3C δ δ
C O
H3C
H3C
H C O
H3C
H3C
H C O
H
H3C
H
electrophile
6
 Consider the following reaction sequence.
O
OH
NaOH
1) LiAlH 4
2) H
B
SOCl2
D
4
CH3
CH3
A
Marks
excess methanol
C
HN(CH 3)2
E
conc. HCl / heat
F
Draw the structures of the major organic products, A-F, formed in these reactions.
A
D
O
O
C
C
O
B
OCH3
E
CH2OH
O
C
N
CH3
CH3
C
F
O
O
C
C
Cl
OH
+
NH2(CH3)2
CHEM1002
2005-N-8
November 2005