2023 F - CH202-4-6 - Final Worksheet Ch7-10 - Org
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Fall 2023 CH202/4/6 Organic Chemistry I
Final Exam Preparation
Worksheet 2 of 2
•
This document includes questions from Chapters 1-6.
•
This worksheet does NOT mean to provide a complete review of the final exam.
Studying only this worksheet is NOT a sufficient preparation for the final exam.
•
This worksheet will not be covered by the review tutorials. Midterm 1 review tutorial
and Midterm 2 review tutorial have covered questions from Chapter 1-6.
•
If you are uncertain about any questions in this document, you are welcome to visit me
during my office hours.
•
There are some questions that you have encountered before this point. When
answering these questions, ensure that you train yourself not to recall the answer, and
ensure that you force yourself to analyze the questions and follow the logic stepwise to
arrive at the final answer.
1.
Which choice shows the transition state for the given S
N
2 reaction?
A.
B.
C.
D.
2.
Which of the solves is more appropriate for the following S
N
2 reaction?
A.
Acetone, (CH
3
)
2
CO, because it is a polar aprotic solvent.
B.
Acetone, (CH
3
)
2
CO, because it is a polar aprotic solvent.
C.
Acetic acid, CH
3
COOH, because it is a polar aprotic solvent.
D.
Acetic acid, CH
3
COOH, because it is a polar aprotic solvent.
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2
of
14
3.
What is the mechanism for the elimination reaction shown?
A.
B.
C.
D.
Page
3
of
14
4.
Which reagents are appropriate to carry out the conversion shown?
A.
NaCl in water
B.
NaCl in ether
C.
HCl in water
D.
TsCl/pyridine followed by NaCl
5.
Provide suitable reagents for the following transformation.
A.
Step 1: HBr,
Step 2: NaOMe
B.
Step 1: HBr, ROOR,
Step 2: NaOMe
C.
Step 1: HBr,
Step 2:
t
-BuOK
D.
Step 1: HBr, ROOR,
Step 2:
t
-BuOK
6.
Which alkyl halide would proceed with the faster rate of S
N
1 reaction?
I
II
A.
I
is faster because it has less steric hindrance.
B.
II
is faster because it has less steric hindrance.
C.
I
is faster because it involves a more stable carbocation.
D.
II
is faster because it involves a more stable carbocation.
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4
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7.
Predict the major product for each of the following reactions.
reaction
major product
a)
b)
c)
d)
8.
Provide suitable reagent(s) to perform each of the following transformations.
reaction
Reagent(s)
a)
Page
5
of
14
9.
For the following mechanism, identify the sequence of arrow-pushing patterns:
A.
Proton transfer
B.
Rearrangement
C.
Nucleophilic attack
D.
Loss of leaving group
10.
Draw the curved arrow on the incomplete mechanism below to complete the mechanism.
Page
6
of
14
11.
What is the IUPAC name of the following molecule?
A.
1-ethyl-6-methylcyclohexene
B.
6-ethyl-1-methylcyclohexene
C.
1-methyl-8-methylcyclohexene
D.
8-methyl-1-methylcyclohexene
12.
Identify the major products generated in the reaction sequence shown below.
A.
I and II
B.
II and III
C.
III and IV
D.
IV and V
E.
III and V
13.
Identify the product of the following reaction that illustrates the correct regiochemical
and stereochemical transformation.
A.
B.
C.
D.
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7
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14
14.
Identify the reagents you would use to achieve each of the following transformations:
Page
8
of
14
15.
Predict the major product(s) for each of the following reactions (A-E):
Reaction #
Major Product(s)
A
B
C
D
E
Page
9
of
14
16.
Assign a systematic (IUPAC) name for the following compound:
A.
2,2,6,6-tetramethyl-3-octyne
B.
2,2,5,5-tetramethyl-3-heptyne
C.
3,3,6,6-tetramethyl-4-heptyne
D.
2-ethyl-2,5,5-trimethyl-3-hexyne
17.
Predict the major product of the following reaction sequence:
A.
B.
C.
D.
18.
What is the major organic product for the following reaction?
A.
(Z)-2,3-dichlorohex-2-ene
B.
(E)-2,3-dichlorohex-2-ene
C.
1,1,2,2-tetrachlorohexane
D.
2,2,3,3-tetrachlorohexane
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10
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14
19.
Identify the reagents you would use to achieve each of the following transformations:
Page
11
of
14
20.
Predict the products obtained when 1-pentyne (CH
3
CH
2
CH
2
C≡CH) reacts with each of the
following reagents:
a.
Excess HBr
b.
One equivalent of HCl
c.
d) R
2
BH followed by H
2
O
2
, NaOH
21.
Predict the product obtained when the following substrate reacts with NaNH
2
in NH
3
followed by MeI (CH
3
I, iodomethane).
22.
Which alkyne would produce the products below through ozonolysis?
A.
HC≡CC≡CCH
2
C≡CH
B.
HC≡CCH
2
CH
2
CH
2
C≡CH
C.
CH3C≡CCH2C≡CCH3
D.
HC≡CCH
2
CH
2
C≡CCH
3
Page
12
of
14
23.
Identify the weakest C-H bond in the given compound, by selecting the highlighted carbon
atom to which the hydrogen atom is attached.
A.
Carbon 1
B.
Carbon 2
C.
Carbon 3
D.
Carbon 4
E.
Carbon 5
24.
Which of the following radicals is the most stable?
A.
B.
C.
D.
E.
25.
Which of the reactions shown is an example of initiation?
A.
B.
C.
D.
26.
Draw one resonance structure for the following radical.
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13
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27.
Select the option that correctly shows the movement of electrons during the process
shown.
A.
I
B.
II
C.
III
D.
IV
28.
Predict the major product(s) of the following reaction:
racemic:
only this enantiomer:
only this enantiomer:
A.
B.
C.
Page
14
of
14
29.
Predict the major product of the following reaction:
A.
B.
C.
D.
E.
30.
Identify all product(s) expected for the following reactions:
31.
Select the product of the reaction of HBr with the alkene shown in the presence of trace
peroxides (ROOR).
A.
B.
C.
D.
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O.
-H
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Question 20 of 32 >
tv
Q
$
#4
↑
© Macmillan Learning
57776
0=0
H
achieve.macmillanlearning.com
H-C-OH
reduction
H-C-OH
H₂C-OH
OCT
11
MacBook Pro
29
<6
Reaction B
Ċ
Chapter 6 HW - General, Organic, and Biological Chemistry for Health Sciences - A-
Resources
? Hint
Submit
Select Draw Templates More
Erase
//
C
0 H
G
8*
(
H
0
H
H➡C
OH
| |
A
OH
H₂C
―OH
9
0
Q2Q
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one molecule is unstable, you can pick any of them to redraw.)
☑
stable
stable
O unstable
O unstable
OH
OH
O:
i
O stable
unstable
HO
Click and drag to start drawing a
structure.
O stable
unstable
:
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a CH₂CH=C(CH3)C₂H5
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b
H₂C
CH3
This hydrocarbon is
CHCECCH(CH3)CH3
This hydrocarbon is
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initial
final
initial
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you can draw any of them.
Explanation
Check
Click and drag to start drawing a
structure.
田
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i
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[0]
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structure.
X
:0
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B 0C1- Assignment 4 - Chapter 4- x
S WileyPLUS
A edugen.wileyplus.com/edugen/Iti/main.uni
WileyPLUS
Brown, Intro Organic Chemistry, 6e
Help I System Announcements
ASSIGNMENT RESOURCES
PRINTER VERSION
Explain why each name is incorrect, and then write a correct name for the intended compound:
OC1- Assignment 4 -
Chapter 4
Problem 4.32
Problem 4.22
Problem 4.20
O Problem 4.42
O Practice Question 04
O Practice Question 06
O Problem 4.14
Problem 4.36
Problem 4.10
E Practice Question 09
Practice Question 07
O Practice Question 05
O Problem 4.30
O Problem 4.34
(a) 2-Ethyl-1-propene
The name is incorrect because
The correct IUPAC name is
(b) 5-Isopropylcyclohexene
The name is incorrect because
The correct IUPAC name is
(c) 4-Methyl-4-hexene
The name is incorrect because
The correct IUPAC name is
Review Score
Review Results by Study
Objective
(d) 2-sec-Butyl-1-butene
The name is incorrect because
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