Tutorials: Organic Chemistry 401_2020
1.
CN
2.
NH N H
O
3. O OCH3
OCH3 NC
NC
O2N
O2N
O
4 K2CO3
Zn/HCl
NO2
Benzene
Br
O
5 O O NH O
H
O
6.
O O 1. NaOEt, EtOH, reflux
EtO OEt
2.
Cl
3. H30+, Heat at high temp.
12. Comment on the selectivity shown in these two cyclization reactions and show their mechanisms.
a) O O
O
cat. HCl
O
O
b) O
KOH, Ethanol
+
O
O O
13. Using the mannich reaction as a guide, suggest a mechanism for this reaction.
NHMe
N
Cat. HCl Me
14. Using michael reaction as a guide, outline the synthesis for compound C from compound A and Compound B
(alpha, beta unsaturated ketone), show all the reagents and conditions.
O O
O
CH3 O OH
+
O
Compound A Compound B Compound C
15. Outline the synthesis for Compound C from given reactants following claised condensation, knoevenagel
condensation, hydroamination and schiff base condensation, show all reagents.
O O HN N
O
+ EtO H
O
Compound A Compound B
Compound C
16. Suggest the mechanism for the transformation showed below including all reagents used:
O
O
17. Outline the synthesis for compound B from Compound A show all reagents and conditions using dieckman condensation as a g
O
O
OEt
N OEt N
O
O
Compound B
Compound A
18. Using enamine alkylation as a guide suggest the mechanism for the following reaction.
O 1. PTSA O
2. NH
i I
3. ii
4. H30+, HEAT H2O
19. Umpolung reaction involves the reverse reactivity of an aldehyde to form a ketone. Outline the mechanism for the transforma
O
O
H
CH3
1
2
Identify the retro-synthetic precursors for the following target molecules:
1.1
1.2
1.3
1.4
1.5
QUESTION 2 [35]
2.1 Outline the synthesis of 2-methyl-3-phenyl-propanoic acid used in the food industry to
preserve and maintain the original aroma quality of frozen foods. Show all reagents and
conditions used. (8)
2.2 Using enamine alkylation followed by Umpolung reaction, outline the synthesis for the
following transformation. Show all reagents and conditions used.
(10)
O O O
O
+ CH3
H3CO H
2.3 Outline the mechanism for the transformation of cinnamaldehyde to 3-methyl-5-
phenyl-4,5-dihydro-1H-pyrazole through Umpulong reaction, show all
reagents. (8)
2.4 Using Dieckman condensation as a guide, outline the synthesis of Compound 2 from
Compound 1, show all reagents and conditions used. (9)
QUESTION 3 [13]
3.1 Suggest possible products for the following reactions: (6)
3.1.1
3.1.2
3.1.3
3.1.4
3.2 Outline the synthesis of cyclopent-3-ene-1,1-dicarboxylic acid from dimethyl
malonate, show all reagents and conditions.
(5)
QUESTION 4 [10]
4.1 Differentiate between homogenous and heterogeneous catalyst and give appropriate
examples for each. (4)
4.2 List three advantages of green chemistry (3)
4.3 Explain why microwave synthesizer is considered as a green chemistry tool? (3)
QUESTION 5 [32]
5.1 Use disconnection (retrosynthetic) approach to synthesize the following compound.
Show both the analysis and synthesis steps: (10)
5.2 Outline the synthesis of the compound, presented below, by using the starting
compound indicated and any other organic/inorganic reagents of your choice: (9)
5.3 Outline the synthesis of the compound, presented below, by using the starting
compound indicated and any other organic/inorganic reagents of your choice: (9)
5.4. By a series of disconnections, determine the possible starting compound that can be
used in the synthesis of the following target molecule. Do not show the synthesis.
(4)
5.4.1