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.
B.
C.
D.
Acetone, (CH
3
)
2
CO, because it is a polar aprotic solvent. Acetone, (CH
3
)
2
CO, because it is a polar aprotic solvent. Acetic acid, CH
3
COOH, because it is a polar aprotic solvent. Acetic acid, CH
3
COOH, because it is a polar aprotic solvent.
Page 1 of 14
3.
What is the mechanism for the elimination reaction shown?
A.
B.
C.
D.
Page 2 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:
B.
Step 1:
HBr,
HBr, ROOR,
Step 2:
Step 2:
NaOMe
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.
Page 3 of 14
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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 4 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 5 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.
Page 6 of 14
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14. Identify the reagents you would use to achieve each of the following transformations:
Page 7 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 8 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
Page 9 of 14
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19. Identify the reagents you would use to achieve each of the following transformations:
Page 10 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 11 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 all resonance structures for the following radical.
Page 12 of 14
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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 13 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.
Page 14 of 14
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|| | | |
| | |
Н-С—С—С—С—С—С—С-С—ОН
| | | | || |
Η Η Η Η Η Η Η Η
Periodic Table and Datasheet
more soluble in water than in oil
O equally soluble in water and in oil
O less soluble in water than in oil
O insoluble in water and in oil
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O
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H
a
A
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C
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A
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B
• You do not have to consider stereochemistry.
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100 degrees
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Complete the table below (answers must be values with proper signs and units).
A[H₂SO4)/At
-0.156 mol L ¹5-1
->>
Δ[02]/ΔΙ
0.260 mol L¹ s1
K₂SO4(aq) + 2 MnSO4(aq) + 8 H₂O(1) + 5 02(aq)
A[KMnO4]/At
Reaction Rate
-0.104 mal L'5" 0.052 MOLL'S!
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Construct the expression for Kc for the following reaction.
CH₂(g) + 2 H₂S(g) = CS₂(g) + 4 H₂(g)
Drag the tiles into the numerator or denominator to form the expression. Each reaction
participant must be represented by one tile. Do not combine terms.
[CH]
[H₂S]²
2[H₂]
2[CH]
[H₂S]*
4[H₂]
Kc =
4[CH]
[CS₂]
[H₂)²
[CH₂]²
1
2[CS₂]
[H₂]*
[CH]*
4[CS₂]
[H₂S]
[CS₂]²
2[H₂S]
[CS₂]¹
RESET
4[H₂S]
[H₂]
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H.
H.
01- sp3, 2 = sp3, 3 = sp3
1 = sp, 2 = sp2, 3 = sp3
1 = sp2, 2 = sp3, 3 = sp2
O 1= sp2, 2 = sp3,3 = sp3
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Just need G and F please
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Step 1: NHẸCH,CH,NH(aq) —
What is the symbol for the equilibrium contant for step 1?
O Kb2
O Ka2
Ο Και
Kbl
Step 2: NH₂CH₂CH₂NH3(aq) =
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CH3
CH3CH₂CHCHCH3
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A
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Construct the expression for Kc for the following reaction.
Question 8 of 35
[H0]
CH,COOH(aq) + H₂O (1) CH,COO (aq) + H₂O'(aq)
Drag the tiles into the numerator or denominator to form the expression. Each reaction participant
must be represented by one tile. Do not combine terms.
Kc =
2[H₂01
[H,0⁰
[H,01
2[H,0²
2[H,0]
[CH₂COO] 2(CH,COO] (CH,COOP 2[CH,COO [CH,COOH] 2(CH,COOH] [CH,COOH!" 2[CH,COOH!"
2[H,01¹
RESET
[H₂O]"
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marks
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Window Help
ORGANIC FUNCTIONAL GROUPS
Identifying primary, secondary, and tertiary alcohols
Explanation
Draw the skeletal ("line") structure of a 3° alcohol with 6 carbon atoms, 1 oxygen atom, at least one ring, and no double or triple bonds.
Click and drag to start drawing a
structure.
Check
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Name these organic compounds:
Η
Η
Η
Η
Η
Η
|||
C=C=C-H
|||
Η Η Η
Η Η
II
H — C =C=C=C=C - H
|||||
Η
structure
Η
Η
Η
Η
Η Η
H H
Η Η Η
|
Η
|||
H – C – C =C=C=C=C=CH
|||||||
Η Η Η Η Η Η Η
name
Π
Π
Π
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Using the table of average bond energies below, the AH for the reaction is
kJ.
ethanol
→ ethene +
water
нн
нн
Н—С—с—0—н
→ Ć=Ċ
+ H-0-H
Bond
сСС-СО-НС-Н СО
AH (kJ/mol) 611 348 464 413 360
-6168
6168
-306
63
46
217
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What is the missing reactant in this organic reaction?
or
R
(0)
Specifically, in the drawing area below draw the skeletal ("line") structure of R.
If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check
the No answer box under the drawing area.
Note: the organic equation above only shows the important organic reactant and product. Minor small-molecule
reactants or products (like H₂O) are not shown.
ONo Answer
Click and drag to start drawing a
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C
X
4:0
Ś
c²
Ć
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