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Chemistry
Date
Jan 9, 2024
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CHEM 293 ________________________ Sample Final Name Dr. H.M. Muchall Make sure that your exam has 10 pages. Show all work. Remember: a point a minute! Textbook and calculator allowed. The textbook can be marked up, but pages must not have been added! 1. (13 points) The following cyclopropane gives rise to an A
2
MX pattern in its 1
H NMR spectrum (400 MHz). a) Identify the groups of signals as to their multiplicities. A: M: X: b) Determine the three coupling constants (in Hz) from the enlarged insets (1 ppm = 15.6 cm). Indicate on the spectrum which lines you use. J
AM
: cm, Hz J
AX
: cm, Hz J
MX
: cm, Hz c) Draw accurate tree diagrams for the A and X signals (10 Hz = 1 cm: use a ruler!). A: X: A
A
M
X
H
H
H
H
MeO
2
C
CO
2
Me
A M X
CHEM 293 Final Exam 2
2. (11.5 points) For the following mass spectrum, give the species from the fragmentations below. Make sure you indicate radical cations, cations or radicals where appropriate. Include the masses of all fragments in the scheme. Also include the type of fragmentation where possible. a) (6.5 points) m/z 118 →
m/z 103 →
m/z 75 b) (5 points) m/z 118 →
m/z 103 →
m/z 47
CHEM 293 Final Exam 3
3. (9 points) Apart from the molar mass, what can you learn (in terms of hetereoatoms or functional groups present) from the molecular ion region of the following mass spectra? Give short (one or two keywords) answers. For each case, which is the molecular ion signal (give its m/z value)? a) m/z: b) c) m/z: d) m/z: (more gentle method) additional information: a normal and a gentler ionisation method used
(enlarged) additional information: the elemental analysis shows C, H, N
m/z:
CHEM 293 Final Exam 4
4. (16 points) Answer the following questions. Circle
TRUE or FALSE. Give a short explanation with an example to clarify the correct or wrong statement. a) The 13
C nucleus never couples with the 1
H nucleus. TRUE/FALSE b) In 1
H NMR spectroscopy, at a low enough field, there are no second order spectra. TRUE/FALSE c) The coupling information in terms of multiplicity from a proton-coupled and an off-resonance proton-
decoupled 13
C NMR spectrum is the same. TRUE/FALSE d) 13
C NMR spectra are not integrated due to the fast relaxation of all 13
C nuclei. TRUE/FALSE e) An ethyl radical is detected at m/z 29. TRUE/FALSE f) An increase in conjugation leads to an increase in the energy required for a UV-Vis absorption. TRUE/FALSE g) The following species fragments in a Retro-Diels-Alder reaction to give a strong signal at m/z 68. TRUE/FALSE h) The following species undergoes a McLafferty-type rearrangement easily. TRUE/FALSE +
.
+
.
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7. Which of the following compounds has the highest A max?
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Please answer correct
Please complete full answer
Please answer.
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1. diethyl malonate
NaOEt, ETOH
2. NaOH, H2O
3. H30*, heat
HO.
Q 2 Q
Alkyl bromide B
Select
Draw
Rings
More
Erase
C
Br
1. diethyl malonate
NaOEt, EtOH
2. NaOH, H2O
3. H30*, heat
HO.
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Please correct answer and don't use hand rating
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Assignment Score:
75.6%
Resources
O Hint
Check Answer
Question 9 of 26
Consider the following reaction.
H,SO,
Predict the product of the reaction. Include all hydrogen
H-O
atoms in your structure.
H.C
CH
H.
Select
Draw
Rings
Erase
More
m
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4.
The following synthesis will fail. Please explain why. (10 points)
1) CH3COCI, AICI 3
2) Zn(Hg), HCI
3) CH3COCI, AlCl3
4) Br2, FeBr3
Br
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Activity 5: Check for Understanding ( 30 mins)
A: Instructions: Assign an JUPAC name to each of the following:
Br
2. CH3-CH-CH=CH3
7. C-
-C!
Br
3. CH3-CH-CH2-CH2
8.
CI
CH3
CI
4. CH3-CH-CH2-CH- CH3
9.
CH3
Br
10.
CI
5.
Br
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SELECT FROM THE FOLLOWING OPTIONS. ONLY ONE IS CORRECT:
F and G
K and E
J and L
G and I
D and G
D and E
C and D
L and H
M and F
A and M
E and B
D and E
G and H
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Please answer fast i will do upvote
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Time lef
what is the best reagent for the conversion shown below?
OH
H3C-CCH-COCH3
H3C-
CHCH,CH,OH
Select one:
Оа. КMNO4
O b. H2/Pd
Ос. 1. NaBHд, 2. НзО"
O d. 1. LIAIH4, 2. H30*
TOSHIBA
B/0
F4
F6
F9
F10
F11
&
7
V
8 A
9.
TYY!
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Your answers are saved automatically.
Remaining Time: 2 hours, 35 minutes, 42 seconds.
* Question Completion Status:
A Moving to another question will save this response.
Question 2
The reaction of sodium ethoxide with iodoethane to form diethyl ether is classified as:
O an electrophilic substitution
O a nucleophilic substitution
O a radical substitution
O an electrophilic addition
A Moving to another question will save this response.
O Type here to search
a.
立
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Question
O Time remaining 56:04
Enter
your answer into th
What is the IUPAC name of the structure below? (small
letters only, no spacing, and please follow proper IUPAC
rules)
Hop
H3C-C=C-C--CH3
ČH3
H3C
ČH,CH3
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The following statements (parts a-e) describe a specific reaction along with its regio- and/or stereo-control. Match the reaction
conditions below (1-8) that correctly corresponds to the statement. Answer with 1, 2, 3, 4, 5, 6, 7, or 8.
H₂
1. Hg(OAc)2, H₂O
1. BH3, THF
H₂
Lindlar's cat.
Pd/C
2. NaBH4
2. H₂O₂, H₂O, OH-
Condition 4
Condition 1
Condition 2
Condition 3
H₂O+
HBr
NaNH,
HBr
H₂O2
Condition 7
Condition 8
Condition 6
Condition 5
a. Reaction condition for the reduction of an alkyne to a cis-alkene.
b. Markovnikov addition of water to a double bond, with no carbocation rearrangement.
c. Anti-Markovnikov addition of HBr to a double bond.
d. Anti-Markovnikov addition of water to a double bond.
e Reaction condition to change 1,2-dimethylcyclohexene into cis-1,2-dimethylcyclohexane.
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Please answer the following question to the fullest and be extremely sure that it is correct and double check. Thank you
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13
eBook
Print
References
10 attempts left
Be sure to answer all parts.
Suggest a reasonable mechanism for the following reaction. Be sure to include all charges and lone
pairs.
CH3
CH3
OC O
CH3
CH3
OH
+
H₂O
CH3
Check my work
CH3
draw structure...
higher MW
H3O*
+
:O:
H
ܐܦܚ
H
H
:O:
H
H
lower MW
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3. Consider the set of test compounds below. Which compound/s will
test positive towards Molisch's Test, Bial's Test and Seliwanoff's Test.
H
H
CH₂OH
H
ОН
H
ОН
0
Н
ОН
Н
-ОН
H НО
H
НО
-H
CH₂OH
||
НО
CH₂OH
1
Н—
HO
НО
ОН
-Н
-Н
CH₂OH
|||
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←
Curved arrows are used to illustrate the flow of electrons. Use
the reaction conditions provided and follow the curved arrows
to draw the missing reactants, intermediates or products of
the following reaction or mechanistic step(s).
Include all lone pairs and charges as appropriate. Ignore
inorganic byproducts.
Problem 14 of
Select to Draw
CH2N2
esc
20
000
FA
#3
A
Pleas
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10.3 Complete the following reactions:
Show the step-by-step process. Do not use shortcut methods. Make it as detailed as it can be.
Encode (not hand-written)!
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C)
CH,CH,-CH-O-
D)
H -O
-CH,CH,-
-H
5. Which of the following compounds is identical to the one shown below?
H.
H.
-C
C-H
H.
H -C
H.
A)
H
H.
H-
H.
H.
H.
H.
B)
H;C
CH,CH3
!!
H.
H.
C)
H-C C C-
H.
H.
H-C-H
H.
H.
H.
H
H
H.
D)
H-
H
H
H -C-H
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How do you answer 7 and 8? (This is for practice and acquisition, not graded; refer to picture one to proceed, please).
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5) A. Showt
B. Draw f
H
H.
но
он
a-D-Fru
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7. The following synthesis are flawed. Explain what is wrong with each:
P
d.
LOH
NH₂
NO₂
1. HNO3,H₂SO4
2. Br₂, FeBr3
3. H₂, Pd/C
1. MeCI, AICl
2. KMnO4, NaOH, heat
3. H₂O*
1. NaNO₂, HCI
2. CuCN
3. MnO₂, DCM
1. NaNH. NHs
2. H₂, Pd/C
3. CF COSH
1. NaOH, heat
2. B₂, FeBrs
CO₂H
CO₂H
CN
NO₂
NO₂
NO₂2₂
LOH
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1. Hg(OAc)2/THF/H2O
?
d)
2. NaBH,ГОн
.CO2C2H5
isi
?
e)
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K
Question Completion Status:
QUESTION 6
Select the missing reagent for the reaction seen below:
Cl₂/AIC13
C1₂
ⒸCl₂/FeCl3
HCI
QUESTION 7
Salert the miceina raanant from tah raaction echama caan haloue
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mercy.blackboard.com
F
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CI
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