Test no. (1)
Name:………………………………………………….. Group:………………………
________________________________________________________
Choose the correct answer:
1. What is the IUPAC name for the following compound?
(a)
1,3-pentamethylpropane
(b)
1,1,3,3-tetramethylbutane
(c)
2,4,4-trimethylpentane
(d)
2,2,4-trimethylpentane
2. Which Newman projection shows the most stable conformation of the following
Compound?
3. The best nomenclature for the geometry of the following compound is...
cis-
trans-
E-
Z-
4.What is the best name for the following compound?
3-methylenehexane
2-propyl-1-butene
4-ethyl-4-pentene
2-ethyl-1-pentene
5. The mechanism of the reaction of propene with H3O+ will proceed through
which of The following intermediates?
6. The reaction of propene with HBr in the presence of ROOR (peroxide) proceeds
Through which of the following intermediates?
7. What is the correct name for this molecule?
a. (2R,3R)-2-bromo-3-chlorobutane
b. (2S,3R)-2-bromo-3-chlorobutane
c. (2S,3S)-2-bromo-3-chlorobutane
d. (2R,3S)-2-bromo-3-chlorobutane
8. Determine the double bond stereochemistry (E or Z) for the following molecules.
a. A: E; B: E
b. A: Z; B: Z
c. A: E; B: Z
d. A: Z; B: E
9. Determine the double bond stereochemistry (E or Z) for the following molecules.
10. Which version of the radical halogenation of an alkane is MOST selective?
a. fluorination
b. chlorination
c. bromination
d. iodination
11. Ozonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A?
a. 2,7-Dimethyl-2,8-nonadiene
b. 2,7-Dimethyl-1,8-nonadiene
c. 2,7-Dimethyl-1,6-nonadiene
d. 2,7-Dimethyl-1,7-nonadiene
12. Which of the following compounds gives a secondary alcohol upon reaction withmethylmagnesium bromide? Assume the usual acid workup.
a. butyl formate
b. 3-pentanone
c. pentanal
d. methyl butanoate
Test no. (2)
1) Name the general class of organic compounds.
2) Circle the more reactive molecule with respect to nucleophilic Acyl substitution.
3) Fill in all the missing products. (12 pts)
4) Fill in all the missing reagents.
5) Draw the mechanism for oneof the nucleophilic acyl substitutions in number 4.
You can use “Ph” for any phenyl rings in your mechanism.
6a) Give the product of the following reaction.
6b) Draw all resonance structures for diazomethane.
7) Benzoic acid can be made from a wide variety of benzene derivatives. Fill in the missing reagents.
I) Draw the structures formula of the following:-
a) 2- methyl-4-penten-2-ol.
b) trimethyl carbonil.
c) Z-1-bromo-1,2- dichloropropene
d) 2R,3S- tartaric acid.
e) 2,4,6- trinitrotolune
II) Arrange the following compounds according to the indicating
property.
a) 2-chlorobutane, t-butyl chloride, 1-chlorobutane and methyl
chloride. ( reactivity towards SN1).
b) methyl carbinol, ethylene glycol, methanol, propane and glycerol.
( boiling point).
c) propene, 2,3—dimethyl-2-butene, trans-2- butane and 2-methyl-2-butene.
( stability) .
d) sec-butyl alcohol, ethyl alcohol and t- butyl alcohol.
( ease of dehydration).
e) dimethyl carbinol, water, t- butyl alcohol and methyl alcohol.
( acidity).
III) Write the reaction mechanisms for the following:-
a) 3-methyl-2-butanol / H+.
b) Ehanol + SOCl2.
c) 3,3-dimethyl-1-butene / HBr.
d) Anisol / HNO3, H2SO4.
e) t- butyl bromide / NaOH
IV)a) Starting from 3-methyl-1-butene, how to prepare the following:-
i) 3-methyl-1- butanol.
ii) 3-methyl-2- butanol.
iii) 2-methyl-2- butanol.
b) Discus the aromaticity of the following compounds:-
V)Complete the following equations:-
Test no. (3)
2. What is the IUPAC name for the following compound?
3.Which Newman projection shows the most stable conformation of the following compound?
4.The best nomenclature for the geometry of the following compound is...
5.What is the best name for the following compound?
6. The mechanism of the reaction of propene with H3O+ will proceed through which of the following intermediates?
7. The reaction of propene with HBr in the presence of ROOR (peroxide) proceeds through which of the following intermediates?
8. What is the correct name for this molecule?
10. Determine the double bond stereochemistry (E or Z) for the following molecules.
11. Which version of the radical halogenation of an alkane is MOST selective?
12. Ozonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A?
13.with methylmagnesium bromide?
a. 3-methylpentanal
b. ethyl benzoate
c. 4,4-dimethylcyclohexanone
d. 4-heptanone
14. Which of the following compounds gives a secondary alcohol upon reaction with methylmagnesium bromide? Assume the usual acid workup.