Test 4, Ch 9,10,11
CHM 2210 – Fall 2012 – Test 4 Name (print):_________________________ 1. What is the IUPAC name for the following compound?
a) b) c) d)
3-methyl-1-penten-4-yne 3-methyl-1-buten-4-yne 4-methyl-4-penten-1-yne 4-methyl-4-buten-1-yne
2.
What is the major organic product obtained from the following reaction? 2 equiv Br2
a) b) c) d)
2,3-dibromobutane 2,2,3,3-tetrabromobutane 2,3-dibromobutene 2,2-dibromobutane
3.
What is the best choice of reagent(s) to perform the following transformation? ?
a) b) c) d)
H2/Pd H2/Lindlar catalyst Na/NH3 BH3; then H2O2, NaOH
1
4. Which of the labelled hydrogen atoms in the following molecule is the most acidic (i.e. most reactive with NaNH2)?
3 2 H H H H H H 1 H H H H 4
a) b) c) d)
1 2 3 4
5.
The structure of the product of the following sequence of reactions would be 1 - NaNH2 2 - CH3CH2Br 3 - H2, Lindlar's Catalyst I II III IV
Br
a) b) c) d)
I II III IV
2
6.
What is the major organic product obtained from the following reaction? O H 1 - BH3 2 - H2O2, NaOH O H OH
I a) b) c) d) I II III IV
II
III
IV
7.
What is the major organic product obtained from the following reaction? O H H2O, H2SO4 HgSO4 O H OH
I a) b) c) d) I II III IV
II
III
IV
8.
What is the major organic product obtained from the following reaction? Li NH3 Na I II III IV NH2
a) b) c) d)
I II III IV
3
9.
In the following elimination reaction, the product(s) of the reaction is(are) CH3O- Na+ 2-bromohexane CH3OH
a) b) c) d) e)
CH3CH2CH2CHCHCH3 CH3CH2CH2CH2CHCH2 An equimolar mixture of a and b. A mixture of the major product a with the minor product b. A mixture of the major product b with the minor product a.
10. Consider the SN2 reaction of butyl bromide with OH- ion. Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and OH- ion? CH3CH2CH2CH2Br + OH- CH3CH2CH2CH2OH +
a) b) c) d)
3-methyl-1-penten-4-yne 3-methyl-1-buten-4-yne 4-methyl-4-penten-1-yne 4-methyl-4-buten-1-yne
2.
What is the major organic product obtained from the following reaction? 2 equiv Br2
a) b) c) d)
2,3-dibromobutane 2,2,3,3-tetrabromobutane 2,3-dibromobutene 2,2-dibromobutane
3.
What is the best choice of reagent(s) to perform the following transformation? ?
a) b) c) d)
H2/Pd H2/Lindlar catalyst Na/NH3 BH3; then H2O2, NaOH
1
4. Which of the labelled hydrogen atoms in the following molecule is the most acidic (i.e. most reactive with NaNH2)?
3 2 H H H H H H 1 H H H H 4
a) b) c) d)
1 2 3 4
5.
The structure of the product of the following sequence of reactions would be 1 - NaNH2 2 - CH3CH2Br 3 - H2, Lindlar's Catalyst I II III IV
Br
a) b) c) d)
I II III IV
2
6.
What is the major organic product obtained from the following reaction? O H 1 - BH3 2 - H2O2, NaOH O H OH
I a) b) c) d) I II III IV
II
III
IV
7.
What is the major organic product obtained from the following reaction? O H H2O, H2SO4 HgSO4 O H OH
I a) b) c) d) I II III IV
II
III
IV
8.
What is the major organic product obtained from the following reaction? Li NH3 Na I II III IV NH2
a) b) c) d)
I II III IV
3
9.
In the following elimination reaction, the product(s) of the reaction is(are) CH3O- Na+ 2-bromohexane CH3OH
a) b) c) d) e)
CH3CH2CH2CHCHCH3 CH3CH2CH2CH2CHCH2 An equimolar mixture of a and b. A mixture of the major product a with the minor product b. A mixture of the major product b with the minor product a.
10. Consider the SN2 reaction of butyl bromide with OH- ion. Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and OH- ion? CH3CH2CH2CH2Br + OH- CH3CH2CH2CH2OH +