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.
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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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2. What went wrong in this situation?
3. What steps should be taken in this workplace to make sure employees are
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Consider the structure below. This substance should be
Η Η Η Η Η Η Η Η
|| | | |
| | |
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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1. CzH5OH(I) + HCOOH(I) → HCOOCzHs + H2O(I)
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3. C₂H4(9) + Cl₂(g) → C₂H4C12(1)
4. C6H6(1) + Br2(1)→ C6H5Br(1) + HBr(g)
5. 2C4H10(9) + 130₂(g) → 8CO₂(g) + 10H₂O(1)
6. 2C7H8(1) + 150₂(g) → 14CO(g) + 8H₂O(1)
Match each equation above with its reaction type.
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→
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◆
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Quizlet
Clutch
E Knowledge Check
Question 9
Black Forest Biologicals, a biotech startup, has a promising Alzheimer's drug candidate Compound SLT-88 entering Phase I trials this year. SLT-88 is the only
product formed by the reaction of two precursor compounds A and B, both of which are quite expensive. The chief medicinal chemist of Black Forest is trying
out different reaction conditions to minimize the cost of manufacturing SLT-88.
In the table below are listed the initial and final amounts of A and B used under two different trial conditions, and also the actual amount of SLT-88 recovered in
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your percentages to the nearest whole percent.
amount of A
amount of B
yield of SLT-88
Trial
initial
final
initial
final
theoretical
actual
1000. mg
0 mg
550. mg
286. mg
999. mg
150. mg
0 mg
1000. mg…
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17 pts
Bookmarks Window Help
Macmillan Learning
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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Please read the question. How do I do it
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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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Decide whether each of the molecules in the table below is stable, in the exact form in which it is drawn, at pH=2.
If you decide at least one molecule is not stable, then redraw one of the unstable molecules in its stable form below the table. (If more than one molecule is
unstable, you can pick any of them to redraw.)
OH
OH
HO
Ostable
Ounstable
O stable
Ounstable
HO
Click and drag to start drawing a
structure.
stable
Ounstable
O stable
Ounstable
☐
X
口:
G
EX
olo
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Construct the expression for Kc for the following reaction.
4 HCI(aq) + O:(g) = 2 H:O(I) + 2 Cl:(g)
1
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
5 RESET
[HCI]
2[HCI]
4[HCI]
[HCIP
[HCIJ*
[0:]
2[0:]
4[O:]
[H:O]
2[HŁO]
4[H.O]
[H:OJ
[CL]
2[CL]
4[CL]
[CL*
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If you decide at least one molecule is not stable, then redraw one of the unstable molecules in its stable form below the table. (If more than one molecule is
unstable, you can pick any of them to redraw.)
HO
☑
O stable
OH
stable
Ounstable
unstable
OH
O stable
O unstable
stable
unstable
G
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CH3
CH3CH₂CHCHCH3
Br
Li
pentane
A
Cul
B
• Draw only products having the organic portion of the original alkyl halide.
• Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium
bond, do not draw the lithium.
Separate products from different steps using the → sign from the drop-down menu.
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Y
II
OH
X + H₂O
H+
H*
OH
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In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement
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Click and drag to start drawing a structure.
C
X
:0
Ś
m
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OTS
OTS
OH
NaOEt
NaCN
EtOH
NaCN
Hexan
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1.6
0.7
1.4
Qy
CH
0.6
1.2
Soret
0.5
1
H
0.4
0.8
0.3
COOCH
0.6
phytyl bacteriochlorophyll a
0.2
0.4
Qx
0.1
0.2
300
400
500
600
700
800
700 750 800 850 900
2 (nm)
2 (nm)
Figure 4.7 Absorption (left) and fluorescence (right) spectra of bacteriochlorophyll a in diethyl ether
5. Look at this figure from Blankenship's book, Molecular Mechanisms of Photosynthesis.
You can see the structure for bacteriochlorophyll a, along with its absorption spectrum.
a. What is the molecular shape around the labeled carbon atom?
b. What is the hybridization around that same carbon?
c. Based on this structure, would you expect this molecule to absorb light in the
visible spectrum? Why or why not?
Absorbance
Fluorescence (Arbitrary units)
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given:
2 NH3(g) + 3 N2O(g) → 4 N2(g) + 3 H2O(D)
N2O(g) + 3 H2(g) → N2H4(D) + H₂O(1)
->>
2 NH3(g) + 12 O2(g) → N2H4(1) + H₂O(1)
H₂(g) + O2(g) → H₂O(n)
AH = -1013 kJ
ΔΗ = -317 kJ
AH = -142.9 kJ
ΔΗ = -285.8 kJ
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Benzene has a 6-carbon ring, with alternating single and double bonds.
Consider a benzene molecule in which a hydrogen atom is replaced by an aldehyde functional group. Draw the molecule produced.
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SCH4U Unit 4 Organic Chemistry
19. Name the following (8)
H
H
| | | |
н-с-с-с-с-с-H
| | | | |
H H 0
CH₂CH₂
HH
CH₂CH₂CH₂
б
OH
H
c=c
CH3
Н Н
H
CH₂CH3
CH3
H
H C
Ontario Virtual School
H-с-с-с-с=c-C-H
H
Н
Н
H-C-H
H
H
CH₂CH₂CH₂-C-CH₂CH₂CH
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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]arrow_forwardH. 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 = sp3arrow_forwardDecide whether each of the molecules in the table below is stable, in the exact form in which it is drawn, at pH=2. If you decide at least one molecule is not stable, then redraw one of the unstable molecules in its stable form below the table. (If more than one molecule is unstable, you can pick any of them to redraw.) OH OH HO Ostable Ounstable O stable Ounstable HO Click and drag to start drawing a structure. stable Ounstable O stable Ounstable ☐ X 口: G EX oloarrow_forward
- Construct the expression for Kc for the following reaction. 4 HCI(aq) + O:(g) = 2 H:O(I) + 2 Cl:(g) 1 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 5 RESET [HCI] 2[HCI] 4[HCI] [HCIP [HCIJ* [0:] 2[0:] 4[O:] [H:O] 2[HŁO] 4[H.O] [H:OJ [CL] 2[CL] 4[CL] [CL*arrow_forwardDecide whether each of the molecules in the table below is stable, in the exact form in which it is drawn, at pH=12. If you decide at least one molecule is not stable, then redraw one of the unstable molecules in its stable form below the table. (If more than one molecule is unstable, you can pick any of them to redraw.) HO ☑ O stable OH stable Ounstable unstable OH O stable O unstable stable unstable Garrow_forwardAnswer questions 3 and 4arrow_forward
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