I will be haPpy to point you in office hours. The SI tutor will hold a pre-exam help 1. Match each definition to one of the terms below. Place the letter of the term in the blank to the left of the definition. heterolytic bond breakage 2 elimination reaction 4 polar reaction 7 electrophile 5 addition reaction 6 radical reaction 8 nucleophile 9 substitution homolytic bond breakage A process involving symmetrical bond breaking and bond making. This occurs when both bonding electrons remain with one product fragment. A reaction where two reactants exchange parts to give two new products. A general term for species which have electron rich sites that can form a bond by donating a pair of electrons to an electron poor site. A general reaction in which a starting material is transformed into two products. a. b. с. d. e. 123

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CHEM 2612 PRACTICE ERAM 2
SMITH ORGANIC CHEMISTRY CHAPTERS 1-7. EMPHASIS ON CHAPTERS 4-7
Bach midterm exam will have 30 questions. They will be in the format of this exam.
I do not post answers because the point of a practice exam is for you to check your
knowledge and to re-read and understand the principles underlying any question about
which you are unsure. If you have questions, see the tutor or I will be happy to point you in
the right direction after class or during office hours. The SI tutor will hold a pre-exam help
session as well.
1.
Match each definition to one of the terms below, Place the letter of the term in the
blank to the left of the definition.
heterolytic bond breakage
elimination reaction
homolytic bond breakage
4 polar reaction
5 addition reaction
6 radical reaction
7 electrophile
8 nucleophile
9.
substitution
a.
A process involving symmetrical bond breaking and bond making.
This occurs when both bonding electrons remain with one product fragment.
A reaction where two reactants exchange parts to give two new products.
A general term for species which have electron rich sites that can form a bond
by donating a pair of electrons to an electron poor site.
A general reaction in which a starting material is transformed into two
b.
C.
d.
е.
products.
2.
Which, if any, of the names shown is correct for:
to
a. isopentadiene
c. 2-methyl-1,3-butadiene d. 2-methyl-2,3-butadiene
e. isobutadiene
b. 3-methyl-1,3-butadiene
The compound CH3-CHCI-CH2-CH=CH-CH2-CH3 contains a single asymmetric center
and a double bond. How many stereoisomers of it exist?
а. 1
3.
b. 2
с. 3
d. 4 e. 5
A correct name for the compound shown is
a. 2-bromo-4-ethyl-3,3,5,5-tetramethyloctane
b. 7-bromo-3-ethyl-2,2,5,5-tetramethyloctane CH3-CH-CH2 C-CH2-CH-CH2-CH3
c. 7-bromo-3-ethyl-2,3,5-trimethylnonane
d. 2-bromo-6-ethyl-4,4,6,6-tetramethyloctane
e. None of the above
4.
CH3
CH3
C(CH3)3
The carbon-carbon triple bond of an alkyne is composed of
a. three o bonds.
C.One o bond and two tt bonds.
e. None of the above is correct.
5.
b. two o bonds and one t bond.
d. three t bonds.
-1-
Transcribed Image Text:CHEM 2612 PRACTICE ERAM 2 SMITH ORGANIC CHEMISTRY CHAPTERS 1-7. EMPHASIS ON CHAPTERS 4-7 Bach midterm exam will have 30 questions. They will be in the format of this exam. I do not post answers because the point of a practice exam is for you to check your knowledge and to re-read and understand the principles underlying any question about which you are unsure. If you have questions, see the tutor or I will be happy to point you in the right direction after class or during office hours. The SI tutor will hold a pre-exam help session as well. 1. Match each definition to one of the terms below, Place the letter of the term in the blank to the left of the definition. heterolytic bond breakage elimination reaction homolytic bond breakage 4 polar reaction 5 addition reaction 6 radical reaction 7 electrophile 8 nucleophile 9. substitution a. A process involving symmetrical bond breaking and bond making. This occurs when both bonding electrons remain with one product fragment. A reaction where two reactants exchange parts to give two new products. A general term for species which have electron rich sites that can form a bond by donating a pair of electrons to an electron poor site. A general reaction in which a starting material is transformed into two b. C. d. е. products. 2. Which, if any, of the names shown is correct for: to a. isopentadiene c. 2-methyl-1,3-butadiene d. 2-methyl-2,3-butadiene e. isobutadiene b. 3-methyl-1,3-butadiene The compound CH3-CHCI-CH2-CH=CH-CH2-CH3 contains a single asymmetric center and a double bond. How many stereoisomers of it exist? а. 1 3. b. 2 с. 3 d. 4 e. 5 A correct name for the compound shown is a. 2-bromo-4-ethyl-3,3,5,5-tetramethyloctane b. 7-bromo-3-ethyl-2,2,5,5-tetramethyloctane CH3-CH-CH2 C-CH2-CH-CH2-CH3 c. 7-bromo-3-ethyl-2,3,5-trimethylnonane d. 2-bromo-6-ethyl-4,4,6,6-tetramethyloctane e. None of the above 4. CH3 CH3 C(CH3)3 The carbon-carbon triple bond of an alkyne is composed of a. three o bonds. C.One o bond and two tt bonds. e. None of the above is correct. 5. b. two o bonds and one t bond. d. three t bonds. -1-
e. If a secondary halide reacts with a nucleophile, it must be S2 and not Sl.
23.
Name the compound shown in the ball and stick
metaphor. Chlorine is green and bromine is dark
red.
24.
The energy peak in a reaction diagram for an S2
reaction is called
The equilbriant
Ohe transition state
e. The activation complex
b. The maximum
d. The intermediate
25.
Which of the following is(are) an electrophile(s)?
a. H30*
b. InCla
c. NH3
d. CH2=CH2
e. 0z
26.
Which of the following is not a nucleophile?
a. Cyclohexene
c. CH2=CH-CI
e. NaSH
b. CH3-C=C-CH3
d. Ammonia
27.
Which, if any, statement concerning the graph shown is
true?
a. The reaction is exothermic
b. The reaction is endothermic
c. The arrow in the center points to the intermediate.
d. The equilibrium constant for the reaction is: K = E, log [AH]²
e. The entropy for this reaction is reversed.
Is the reaction shown an example of
a. addition
b. elimination
C. substitution
d. rearrangement
e. None of the above
28.
Br2
Br
catalyst
Is the reaction shown an example of
a. addition
d. rearrangement
29.
b. elimination c.substitution
e. None of the above
NaNg
H
30.
The reaction of isopropyl bromide with sodium methoxide to give methyl isopropyl
ether
a. could occur by an Sy1 mechanism.
-5–
Transcribed Image Text:e. If a secondary halide reacts with a nucleophile, it must be S2 and not Sl. 23. Name the compound shown in the ball and stick metaphor. Chlorine is green and bromine is dark red. 24. The energy peak in a reaction diagram for an S2 reaction is called The equilbriant Ohe transition state e. The activation complex b. The maximum d. The intermediate 25. Which of the following is(are) an electrophile(s)? a. H30* b. InCla c. NH3 d. CH2=CH2 e. 0z 26. Which of the following is not a nucleophile? a. Cyclohexene c. CH2=CH-CI e. NaSH b. CH3-C=C-CH3 d. Ammonia 27. Which, if any, statement concerning the graph shown is true? a. The reaction is exothermic b. The reaction is endothermic c. The arrow in the center points to the intermediate. d. The equilibrium constant for the reaction is: K = E, log [AH]² e. The entropy for this reaction is reversed. Is the reaction shown an example of a. addition b. elimination C. substitution d. rearrangement e. None of the above 28. Br2 Br catalyst Is the reaction shown an example of a. addition d. rearrangement 29. b. elimination c.substitution e. None of the above NaNg H 30. The reaction of isopropyl bromide with sodium methoxide to give methyl isopropyl ether a. could occur by an Sy1 mechanism. -5–
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