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The Islamic University of Gaza
CHEM 2311
Faculty of Science
09/06/2009
Final exam
Exam page: 4
Chemistry Department
Time allowed: 2 hour
Student Name:
Student ID. No.
50
First Question
(15 marks)
Which of the following scientific statements are true and which are false?
1) [
] 2 molecules of Formaldehyde react together to form Aldol product
2) [
] Phenol exists mainly in the more stable keto form
3) [
] Acetal is a chemical specie in which both of alcohol and ether functional
groups are on the same carbon atom.
4) [
] 2-Methyl cyclohexane amine is more basic 2,6-dimethyl cyclohexan amine
5) [
] The oxidation product of p-xylene is benzene dioicacid (terephthalic acid)
6) [
] Any aromatic amine reacts with nitrous acid to form aryldiazonium ion
7) [
] Asymmetric ethers are generally synthesised by dehydraton of alcohols
8) [
] It is easily to cleavage the ether bond under acidic conditions.
9) [
] The reaction of Butanol with HCl is faster than the reaction of t-butyl alcohol
10) [
] Hydrolysis of ester under basic conditions is known as saponification
11) [
] The order of alcohol dehydration is 3ͦ > 2ͦ > 1ͦ
12) [
] In acid dehydration of 2-methyl-2-butanol the major product is 2-methyl-1butene
13) [
] Keton is the product of reaction between one equivalent of Grignard reagent
and ester
14) [
] Oxidation of ketone to alcohol is faster than the oxidation of aldehydes
15) [
] The α hydrogen of an ester is strongly acidic and can be removed by weak
base
1
Second Question
(15 marks)
1) Name and/or draw the structures of the following compounds
H2N
O
NH2
OCH3
NH2
OH
(7 marks)
O
O
Vanillin
Dicyclopropyl ether
N,N-dimethyl acetamide
Answer the following quations
(8 marks)
1) Write the formulas for Keto & Enol form of acetone
2) Which is more acidic ethanol or trifloroethanol? Explain your answer
3) Which is more reactive aldehydes or Ketone? Why?
4) which is more acidic; the α hydrogen of ester of the α hydrogen of aldehyde? Why?
2
Third Question
(20 marks)
Complete the following chemical equations (write all the possible products)
H2O
1)
PhCH2MgCl + CO2
2)
(CH3)3COH + HCl
3)
15 min
?
1-pentanol + PCC
4)
5)
rt
OC(CH3)3
O
H+
?
+
H2O
+ HOCH2CH2OH
?
?
H+
6)
Benzaldehyde + 5eq CH3OH
7)
O
CH3CH2CCH2CH3 + CH3CH2MgBr
8)
Acetyl chloride + NH3
9)
10)
O
O
+
CH3CH
CH3CH
?
OH
H+
CH2CH2CH2COOH
OH
11) CH CH CH OH
2
2
3
Jones reagent
12) Acetone +3 HCN
KOH
?
13) Cyclohexanone + Hydrazine
14) 2-butenal
NaBH4
15) cyclohexanone
?
NaOCH3
CH3OD/ 10 eq
3
+ H2 O
H+
H2O
LiAlH4
Fourth Question
(20 marks)
How you can synthesize the following compound from the given starting material
A) m-dibromobenzene from benzene
(4 marks)
B) phenylacetic acid from bromobenzene and other reagents
(4marks)
C) Butanoic acid from 1-bromopropane
(4 marks)
D) Ethyl butanoate from Ethyl acetate
(4 marks)
2) Write the chemical and the reaction mechanism for the reaction of benzaldehyde
with excess methanol and acid catalyst.
(4 marks)
‫تمنياتي لكم بالتوفيق و النجاح‬
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