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Worksheet No. 2 Organic Chemistry 2: Aldehydes and Ketones
kadecastro-cruz 1
Solve the following problems systematically in your notebook. Be
able to show the mechanism for each problem. PREPARATION OF
ALDEHYDES AND KETONES 1. Predict the product for the following
reaction.
PCC
CH2Cl22-hexanol
2. Predict the product for the following reaction.
OH
CH2OHPCC , excess
CH2Cl2 3. Compound A on ozonolysis yields acetophenone and
propanal. What is the structure of compound A?
Compound A1. O32. (CH3)2S
Acetophenone + propanal
4. Provide the reagents necessary to carry out the following
conversion.
(CH3)2CHCH2C CCH2CH(CH3)2 3-methylbutanal 5. Predict the product
for the following reaction.
H2O / H2SO4
HgSO4
6. Provide the reagents necessary to carry out the following
conversion.
O
7. Predict the product for the following reaction
AlCl3
OCl
REACTIONS OF ALDEHYDES AND KETONES 8. Provide the structure of
the product, when cyclohexanecarbaldehyde reacts with excess
2-propanol in presence of sulfuric
acid. 9. Predict the product for the following conversion.
O
O
O
H3O+
1 mol
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Worksheet No. 2 Organic Chemistry 2: Aldehydes and Ketones
kadecastro-cruz 2
10. Predict the product for the following reaction.
HO
O
HH2SO4
11. Predict the product(s) for the following reaction.
H3O+
O
O
12. Predict the product for the following reaction.
O
HH2SO4
OH
13. Predict the product for the following reaction and provide a
curved arrow mechanism for the formation of the product.
HOCH2CH2OH
H2SO4
O
14. Predict the product, when pentanal reacts with methanamine
in presence of acid catalyst 15. Predict the product, when
4-methyl-2-hexanone reacts with hydrazine in presence of acid. 16.
Predict the product for the following reaction and provide a curved
arrow mechanism for the formation of the product.
NH2OH
H2SO4
H
O
17. Predict the product for the following reaction.
ONH2NHCNH2
O
H2SO4 18. Predict the product for the following reaction
sequence.
CH2CH2OH
PCC (CH3)2NH
19. Provide the reactant(s) necessary to prepare the following
compound.
N
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Worksheet No. 2 Organic Chemistry 2: Aldehydes and Ketones
kadecastro-cruz 3
20. Provide the product for the following reaction
1. NH2NH2, KOHOH
O
O
2. H3O+
21. Predict the product for the following reaction.
CH
CH
O
O
NH2NH2, KOH
excess
22. Provide the product for the following reaction sequence.
CH2CH3
CH3CH2CH2CCl
O
AlCl3 H2SO4
Raney NiHSCH2CH2SH
23. Provide the reagents necessary to carry out the following
conversion.
O
H
O OH
H
O
24. Predict the name of the product for the following reaction
sequence.
OHPBr3 H
O
PCCMg/ether
2. H3O+
1.
25. Provide the reagents necessary to carry out the following
conversion.
Br
O
26. Provide the structure for X, Y and Z, for the following
reaction sequence.
Br
XCH3CH2CH2CH2Li
YCH3CCH2CH3
O
+ Ph3Pether
Z
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Worksheet No. 2 Organic Chemistry 2: Aldehydes and Ketones
kadecastro-cruz 4
27. Provide the structure of the reactants necessary to prepare
the following compound using Wittig reaction.
28. Predict the product of the following reaction sequence.
O
CH3COOH
O
29. Suggest a stepwise synthesis of 1-phenylpropanal from benzyl
alcohol. 30. Suggest a stepwise synthesis for the following.
O
OH
