Lab+Lecture+9+-+Methyl+Diantilis_Formal+Lab+Report_Annotated_2023Oct24
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1
CHEM 12AL
Organic Chemistry Lab
2
Synthesis of Methyl Diantilis
1)
Two step synthesis
- Everyone performs the first step of the reaction
- Split into 4 groups of 4 and carry out second step to produce different products
2)
Combine all techniques up to this point
- Set up reactions
- Purify intermediates and final products
- Characterize products by 1
H NM and 13
C NMR
3)
Formal Lab report is written based on Methyl Diantilis Synthesis
- Detailed formal lab report guidelines available on bCourses
3
Synthesis of methyl diantilis
Two steps: i) aldehyde reduction, ii) etherification
NaBH
4
reduction mechanism
⊥
H-
0
-
H
-
N
Hy
-
0
-
Hz
I
is
oft
->
Ot
ON
.
not
a
1
,
'Yout
3
equiv
of
hydride
remaining
(H0)
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4
Amberlyst-15 (H
+
) catalyzed etherification mechanism
Synthesis of methyl diantilis
Two steps: i) aldehyde reduction, ii) etherification
Sheterogeneous
H
*
/Acid
Catalyst
Ju
T
⑰
i
,
it
"
In t
-
-
"
os
wo
,
an
I
->
dH
·
benzylic
cation
R
-OH
·
resonance
stabilized
↓
F
·
Sul
-
H
I
hi
It
en
1
-
I
·
similar
stability
tab"
catius
In
-Ott
·
compare
purity
5
•
Due on Monday, Dec 4 (30pts)
•
Typed: 12pt font, double spaced
•
Page count: 3-5 pages including figures
•
Use ChemDraw to draw molecules and reaction schemes
•
Formal Lab Report is a separate assignment to the experimental lab notebook.
*
Can not be used as your dropped lab score*
Synthesis of methyl diantilis –
Formal Lab Report
Formatting Guidelines
•
Use ChemDraw to draw molecules and reaction schemes
•
Formal Lab Report is a separate assignment to the experimental lab notebook.
6
Synthesis of methyl diantilis –
Formal Lab Report
Lab Report Outline
1) Introduction
2)
Results and Discussion
3) Conclusion
4) Experimental
5) References
6)
Supplemental Information
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7
Synthesis of methyl diantilis –
Formal Lab Report
Lab Report Outline
Introduction [5 pt]
•
Introduce the synthesis of methyl diantilis in general (why it’s important, etc). In this introduction, include at least two reference to a peer-reviewed journal article. Indicate the references using superscripted numbers which correspond to a numbered list of properly formatted citations at the end of the report. •
Draw a reaction scheme for the specific reactions that you carried out. •
Describe this reaction scheme in 2-3 sentences.
Results, Discussion, and Conclusions [10 pt]
•
Write a summary of your results.
•
Write a cohesive discussion regarding the experimental details for the reaction that you carried out. Your discussion should include:
An analysis of all NMR spectra of your group
A rational arrow-pushing mechanism for both reactions
A discussion of your yields with all four alcohols
Discuss the composition of each product. In this discussion, include information gained from TLC as well as 1
H NMR and 13
C NMR. Include the purity calculations and a qualitative comparison of your group’s products with the products from other groups in your lab section.
Describe the experimental factors that you believe had the biggest effect in causing any variability between different groups in your laboratory section. •
Write a concise conclusion that summarizes the results of your experiment.
8
Synthesis of methyl diantilis –
Formal Lab Report
Lab Report Outline
Experimental [6 pt]
•
Write a concise description of the steps that were taken to carry out this reaction in the lab. This should be written in the third person passive tense and should constitute an overview of the procedure without including all the details. •
Report the 1
H NMR and 13
C NMR data for your intermediate and products.
References [2 pt]
Formatted according to the American Chemical Society style
Supporting Information: [7 pt]
Attach copies of each NMR spectrum, annotated as typical for this course.
9
NMR Spectroscopy
1
H NMR of Aromatic Molecules
- Circulating pi electrons create ring currents
- Induced magnetic field increases B
effective
near H atoms
Increase in B
effective
deshields H atoms and shifts
downfield benzene
ethylene
Induced magnetic field
B
0
Induced magnetic field
= 6-8 ppm
= 5-6 ppm
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10
NMR Spectroscopy
1
H NMR of Aromatic Molecules
2-Isopropylphenol
7.00
6.75
7.25
7.50
1.0
1.0
1.0
1.0
7.35
7.21
7.01
6.80
Ch
-
He
Haz
CHf
H
!
Ad
·
4
sets
of
aromatic
'It's
f
·
complex
splitting
-
Of
He
11
NMR Spectroscopy
1
H NMR of Aromatic Molecules
7.00
6.75
7.25
7.50
1.0
1.0
1.0
1.0
7.35
7.21
7.01
6.80
How do we assign the aromatic protons given the information that we have available: i) Chemical shift
values
, ii) Peak Areas
, and iii) Peak Splitting
?
Origins of aromatic 1
H Chemical Shift Values
Consider
ring
substituent
resonance
forms
⊥
it
*
3
Elite
j
I
↑
-
=I
E
-
OH
is
pi-donating
I
I
-
I
->
lone
pairs
on
oxygen
donate
intoring's
shield
ortholpara
positions
-
-oH
is
withdrawing
->
oxygen
is
more
dectronegative
than
carbons
is
an
Eltria
the
o-csigma
bond
,
hart
to
predict
mary
:
substituents
affect
shielding/deshielding
of
aromatict's
in
sometimes
wats
.
12
NMR Spectroscopy
1
H NMR of Aromatic Molecules
7.00
6.75
7.25
7.50
1.0
1.0
1.0
1.0
7.35
7.21
7.01
6.80
Origins of aromatic 1
H Chemical Shift Values
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13
NMR Spectroscopy
1
H NMR of Aromatic Molecules
Origins of aromatic 1
H Peak
Splitting
3-bund
coupling
Hist
1X
I
I
ing
strengths
-H
1
Ortho
-
H
-
- H
or
tho
coupling
:
6-10
Hz
(normal
3-bond
coupling)
pare
#
meta
coupling
:
1-3Hz
(4-bond
coupling)
para
para
coupling
:
0-1H1
/S-bond
coupling
(
·
Conjugation
enables
long-range
coupling
·
S-bond
coupling
is
uncommon
in
nonvaromatic
systems
14
NMR Spectroscopy
1
H NMR of Aromatic Molecules
7.00
6.75
7.25
7.50
Origins of aromatic 1
H Peak
Splitting
fanity
t
3-bond
coupling
⊥
a
Stab
,
"Ybc
,
"Tod
Ab-lit
I
-
·
Ha
or
Hd
e
ef
4-bund
coupling
HborHe
-
"Fac
,
"
Abd
Hb:
He
have
more
coupling
Partiers
15
NMR Spectroscopy
Aromatic 1
H Splitting trees
3
J
a
b
= 8 Hz
4
J
a
c
= 2 Hz
3
J
d
c
= 8 Hz
4
J
d
b
= 1 Hz
1 box = 1 Hz
↑
Ha
Ald
--
--
N
-
Ha-Hb
/Ortho)
N
↑
Hd-H
,
(orthol
-
8
-
-
r
IT
Ha-He
(metc)
l
Hd-Hb
(meta)
1
:
1
:
I
:
1
1
:
1
iii)
I
I
us
it
te
-
doublets
of
doublets
doublets
of
doublets
(dd]
(dd]
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16
NMR Spectroscopy
Aromatic 1
H Splitting trees
3
J
b
a
= 8 Hz
3
J
b
c
= 7 Hz
4
J
b
d
= 1 Hz
3
J
c
d
= 8 Hz
3
J
c
b
= 7 Hz
4
J
c
a
= 2 Hz
1 box = 1 Hz
⑧
⑧
Hb
Ha
I
N
-
=
Hb-
Ha
(orthol
F
->
Ha-Hd
(ortha)
V
8
8
---
--
I
-
-
8
y
8
S
/Hb-Hc(orthol
-
-
TH
-
Hb
lot
#
T
ST
Ab-Hd
(metal
11
is
is
~
MHc-Ha
1
:
1
2
:
2
1
:
1
:
I
2
:
2
1
:
I
expected
Mee
le
triple
of
doublets
triplet
of
doublets
(
+
d)
(
+d)
17
NMR Spectroscopy
1
H NMR of Aromatic Molecules
7.00
6.75
7.25
7.50
1.0
1.0
1.0
1.0
7.35
7.21
7.01
6.80
C
-
He
n
CH
Ad
Hc
Hb
Ha
-
dd
dd
I
d
Id
HA
-
OH
He
Related Questions
need help labeling my chart please help information, there
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Organic Chem 1 Week 5 Lab- Student.docx - Saved to this PC -
P Search
shiku
sign
Layout
References
Mailings
Review
View
Developer
Help
OFir
A Aa Ao
AaßbCcDd AaBbCcDd AaBbCc AaBbCcD AaB
& Re
A
== Ev vv
1 Normal
1 Heading 2
1 No Spac. Heading 1
Title
A Se
Paragreph
Styles
Editi
6. In an organic chemistry lab, chemists were attempting to convert compound I into compound III
via a substitution reaction. To their surprise, compound II was the only obscrved compound after
treating compound I with cyanide.
:CEN :
CN
CI
CN
observed
not observed
a. Provide a detailed, stepwise mechanism for the transformation above that accounts lir the
formation of pruduct II. Use the curved arrow lurmalism to show the tlow of clectroLs. Shew
all lene pairs, intermediates, formul charges, und pertinent resonance structures.
rited States
l n Fa Accesibility: Inwestigate
lext Predictinrs: O
D' Fucus
99+
**
F10
F11
PrtSc
F12
%23
3
4.
8
E
T.
Y
G
H
J
K
C
M
Alt
Ctri
V
N
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Answer D and e and F
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Show work with explanation needed. Don't give Ai generated solution
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Answer a b and c
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ew topic
[References
Draw both resonance structures of the anion formed by the reaction of the most acidic C-H bond of the compound below
with base.
H3C
SCH3
• Include all valence lone pairs in your answer.
• For structures having different hydrogens of comparable acidity, assume that the reaction occurs at the less-
substituted carbon.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right
corner.
• Separate resonance structures using the → symbol from the drop-down menu.
C
P
opy aste
11:58 M
18
52%
4/11/2021
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Help please! Bond drawings please!
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ES
Window
Help
achieve.macmillanlearning.com
Learning
Macmillan Learning
Classify each molecule as an aldehyde, ketone, or neither.
←
Aldehyde
O=
CH3CH2CH2CH
X
a
Thu Oct 10
Chapter 6 HW - General, Organic, and Biological Chemistry for Health Sciences - Achieve
Resources
? Hint
Submit Answer
Ketone
Neither
Answer Bank
OH
H3C-O-CH2CH3
CH3CH2CCH3
CH3CHCH3
O=CH
CH₁₂CHCH3
CH3CH2CH=CH2
OCT
10
MacBook Pro
&
¥5
%
ZA
@
(
>
ㄓ
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Please correct answer and don't used hand raiting
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Draw in the starting material below
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Use the information in the pK table to rank the molecules in order of decreasing basicity. For exam
and "2" for the next strongest base and so on.
CH3NH₂
H
HSO4
HS
Molecules
(Choose one)
(Choose one)
(Choose one)
(Choose one)
X
CH1
NH₂
H₁₂
CH,NH,
H₂O
CH₂OH
48
38
36
33
15.7
15.5
pk₁ table
a
CH,NH,
CH, SH 10.4
HCN
NH
H₂S
CH,CO,H
10.6
9.4
9.2
7.00
4.76
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Hi, both answers are incorrect. Can you recheck it?
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Pls help ASAP
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3 attempts left
Check my work
Be sure to answer all parts.
Draw the products of the following acid-base reaction. Do not draw lone pairs in your answers.
When drawing a hydrocarbon use a skeletal structure.
CH C C-H
NaNH2
Na
draw structure...
draw structure
conjugate base
conjugate acid
Prev
5 of 28
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Please answer all questions
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Learning Target 3
Criteria for satisfactory score
All molecular drawings must be valid Lewis structures (octet rule, formal charge, valence, geometry). Curved arrows will
be interpreted very strictly. Thus, they must clearly indicate the origin and destination of electron delocalization.
Tasks
1. Generate at least four reasonable resonance structures for the molecule shown in Figure 1 by drawing curved ar-
rows and the resulting structure next to it (indicate reading direction by numbering structures and writing the or-
der for the reader to follow).
2. Select the most significant and least significant resonance contributor and explain your
choice.
NH
Figure 1: Compound 3
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Show work. Don't give Ai generated solution
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Need help with number 4.
Theses are pre lab questions and not homework. Was rejected once and unsure why. Pre lab means before the actually lab we do (which that part is graded)
Thanks
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None
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Select the best answer.
HO
CI
i.e.
R
1
The aromatic group will bé abbreviated as "R" in the
potential answers to questions 2-6 in this quiz.
a.)
b.)
c.)
S(O)Cl,
NaCI
HCI
d.)
e.)
HCIO,
Cl,
a.)
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Provide a name for each of the following molecules.
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Please answer 10-20
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I understand where the proton transfer occurs but not what the products will look like. Can you draw curved arrows to show proton transfer and what the reaction products would look like? And explain which side is favored and why
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e) f) HBr Mg°, ether CO2.
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Please correct answer and don't use hand rating
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- need help labeling my chart please help information, therearrow_forwardOrganic Chem 1 Week 5 Lab- Student.docx - Saved to this PC - P Search shiku sign Layout References Mailings Review View Developer Help OFir A Aa Ao AaßbCcDd AaBbCcDd AaBbCc AaBbCcD AaB & Re A == Ev vv 1 Normal 1 Heading 2 1 No Spac. Heading 1 Title A Se Paragreph Styles Editi 6. In an organic chemistry lab, chemists were attempting to convert compound I into compound III via a substitution reaction. To their surprise, compound II was the only obscrved compound after treating compound I with cyanide. :CEN : CN CI CN observed not observed a. Provide a detailed, stepwise mechanism for the transformation above that accounts lir the formation of pruduct II. Use the curved arrow lurmalism to show the tlow of clectroLs. Shew all lene pairs, intermediates, formul charges, und pertinent resonance structures. rited States l n Fa Accesibility: Inwestigate lext Predictinrs: O D' Fucus 99+ ** F10 F11 PrtSc F12 %23 3 4. 8 E T. Y G H J K C M Alt Ctri V Narrow_forwardAnswer D and e and Farrow_forward
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