Organic chem 1 test 1
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Organic Chemistry I Exam I 02/09/2023 - 02/10/2023
1) A nitrogen with two bonds has _______ lone pair(s) and would carry a formal charge of _______?
A.
0, 1+
B.
1, 1-
C.
2, 1-
D.
1, 0
E.
2, 1+
2) In the following molecule, what type of orbital is the lone pair in?
A.
unhybridized s
B.
unhybridized p
C.
sp³ hybridized
D.
sp² hybridized
E.
sp hybridized
3) Which of the following terms describes why primary alcohols are more acidic than secondary and
tertiary alcohols?
A.
Induction
B.
Resonance
C.
Lewis acid-base complex
D.
Solvating effect
E.
Leveling effect
4) Which of the following compounds is the most basic?
5) Constructive interference of waves results in _________.
A.
A covalent bond
B.
A wave with larger amplitude
C.
Cancelation of both waves
D.
Formation of a node
E.
Both A and B
6) Which of the following is the correct condensed structure for the following compound?
A.
CH
₃
C(CH
₃
)
₂
(CH
₂
)
₂
(CH)BrC(CH
₃
)
₂
B.
CH
₃
CH
₃
CH
₃
C(CH
₂
)
₂
C(CH
₃
)
₂
CHBr
C.
(CH
₃
)
₃
C(CH
₂
)
₃
BrCHCH
₃
CH
₃
D.
CH
₃
CH
₃
CH
₃
C(CH
₂
)
₂
CHBrCHCH
₃
CH
₃
E.
(CH
₃
)
₃
C(CH
₂
)
₂
CHBrCH(CH
₃
)
₂
7) Distillation is a technique used in the purification of volatile liquids by taking advantage of their
differences in boiling point. If a mixture of water, isopentane, acetone, sec-butanol, and isopropanol was
found, what is the order in which the compounds would be purified (low boiling chemicals distill first)?
Provide your answer by placing a number (1-5) in each box under the appropriate structure.
8) A recent publication on strategies against melanoma contained the following molecule (4-S-CAP).
a)
Clearly label the structure with each functional group found in the molecule.
b)
Which functional group contains the most acidic proton?
c)
An intermolecular proton transfer can take place with this compound. Draw the product formed
from this proton transfer and add mechanism arrows to the structure on the left to justify your
product (Next page).
9) In 1935, Louis Hammet noticed a relationship between the substituent in the para position of benzoic
acid and the acidity of the carboxylic acid. Using your knowledge of factors that influence acidity, rank
the following benzoic acids from 1-5 (1 = most acidic. 5 = least acidic)
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Related Questions
5. Redraw the following structures below in Lewis form, filling in all of the implied carbon atoms and hydrogen
atoms.
6. The following are the reagent, intermediate, and product in a reaction you will learn later in Organic
Chemistry.
a. Identify any formal charges that are missing from the structures.
b. Draw in all lone pairs.
c. Redraw the structures with all hydrogen atoms.
to t
OH ₂
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Hi! Can someone please help me with these 2 questions? Thanks so much!!
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4.
One of the resonance structures of "tropylium ion" (C7H7*) is shown below. It is planar and
aromatic with Hückel number of p-n electrons where n=1. Draw all the other contributing resonance
structures. (There are more than two.)
Based on the “average" of the contributing resonance structures, how close does the average ring carbon
get to its "octeť" in tropylium ion?
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10. Name the following structure.
11. Of these two resonance structures, the greater contribution to the resonance hybrid is from
the second one. Based on what you know about charge stability, does this make sense? How
can you explain this observation, with everything you know about resonance forms?
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Please answer only question 3
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Table 1.1: Bond Angles of Selected Molecules
Bond-line Structure
to those you would
Approximate Bond Angle
180
:NEC
H-Be-H
:0:
120
H.
H.
B-
H.
Critical Thinking Questions
9 Use VSEPR to explain why the ZHBH bond angle of BH; is 120°. (Hint: What is one-third se
360°?)
10. Both the HCH and ZHCO bond angles of H2CO (formaldehyde) are very close to 120°, but one
is slightly smaller than the other. Predict which is smaller, and explain your reasoning.
11. Use VSEPR to assign a value of "close to 180" or “close to 120" to each bond angle marked
with a dotted line. (These angles are drawn as either 90° or 180°, but may be another value.)
H
O: 0-H
H
H.
H
H N:
H
H
H
:N C:
H C H
H-
CH
H CCE
H-
CC C-H
ol doss itmbT
12. Consider the following flat drawing of methane (CH4).
What is ZHCH bond angle implied by this drawing if you assume it is flat?
a.
H -C-H
b.
Are the electron domains of this flat CH4 spread out as much as possible?
C.
Use model materials to make a model of CH4 (methane). If you…
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8
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1. What is resonance contributor in which one or more atoms bears a formal change and the most stable resonance form?
2.what is the process of distributing electron pairs in a molecule?
3. Are organic molecules which are less sterically hindered more attractive than those which are more sterically hindered?
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18. What type of bonds hold organic molecules together? How are they different than the bonds that
hold inorganic molecules together? Be specific, I want more than just names of bonds.
19. For the following molecule draw in all the dipole moments using 6+ and 6.
XX
20. BONUS: Why can an sp² hybridized carbon not form a double bond?
7
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The following bonds in vinyl alcohol, what is the bond angles for C-O-H? See the structure as your basis.
...
нн
H-c=c-ö-H
A) 109.5°
B) 90°
c) 180°
D) 120°
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Please solve this
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8. a) State the hybridization (sp°, sp', sp) of each
carbon in this molecule, going left to right.
HC
b) Write "most" under the most stable alkene.
Write "least" under the least stable alkene.
c) Write "most" under the most stable cation.
Write "least" under the least stable cation.
CH2
CH3
CH3
CH3
CH3
H3C
CHT
HC
H3C
ONLY roactions we have studied this semester.
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CH3+ and CH3- are two highly reactive carbon species.
a. What is the predicted hybridization and geometry around each carbon atom?
b. Two electrostatic potential plots are drawn for these species. Which ion corresponds to which diagram and why?
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5 please, if you can help with me with the other one.
thank
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Electron
Groups
shape
(EGs)
2.
Total
smallest
90°
120°
180°
number
angle
of bonded
atoms
shape
(B.P) +
lone pairs
(L.P) on
smallest
centre
90°
109°
120°
angle
atom
Discuss with your neighbours and provide answers to the following questions. Circle the words
that make each statement correct.
1) Each row represents different possible arrangements of that number of electron groups (EG).
In each structure, the EGs get [ closer together / further apart ] and the angles between them
get [smaller /larger ].
2) The observed structures adopted by real molecules are those in the thick borders.
These structure have the [ smallest / largest ] angles and the EGs are the [ closest together
| furthest apart ].
3) The preferred structure is adopted because this [ minimizes / maximizes ] the [ repulsion /
attraction ] felt between all EGs.
(Clue: what does VSEPR stand for?)
3.
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1. What is the formal charge on the nitrogen in the following structure?
H
a. 2
b. 1
c. 0
2. Explain your answer (show your work) to question 1 below
a.
3. What is the relationship between the following structures?
C.
4. Which of the following compounds is not an organic compound.
a. CH3N₂
c) CsH18
d) H₂O
b. CH3COCH 3
5. Which of the following is the correct depiction of the dipole for a C-F bond?
d. -1
e. -2
a. Same molecule
b. Different unrelated molecules (not isomers)
c. Constitutional isomers
O
H-N-NEN
C-F
ⒸN=N=0:
H-C
H
a
N=N
H
C-F
b
6. Which of the following pairs are valid resonance structures of each other?
H-N-NEN
1
C
d
d.
H₂C=
O
H₂C-N=N
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help
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5. - For acetone, CH3COCH3
A) Draw the Lewis structure and describe the hybridization of for each carbon atom in acetone
B) Show o and n bonds on the Lewis structure. How many o and how many a bonds present in
acetone?
C) Draw a complete orbital overlap diagram showing all bonds, lone pairs, and bond angles.
D) Identify each individual orbital and label the diagram with the o and a bonds. Show the bond
composition (which type of overlapping orbital) for all o bonds.
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Oo.37.
Subject :- Chemistry
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Remaining Time: 1 hour, 11 minutes, 56 seconds.
* Question Completion Status:
A Moving to the next question prevents changes to this answer.
Question 8
How many unhybridized p-orbitals are in the carbon label b in the structure below?
O A. 1
B. 2
DC. 3
OD.4
O E. O
4. Unit 4 - Diastereo..m4v
Deen fle
3. Unit 4 - R And S..m4v
Open file
1. Unit 4 - Introduct..m4v
Cpen file
earch
a
99
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7. Tropolone (A) is a molecule that easily loses a proton (H+) to form a relatively stable
anion (B). In tropolone (A), the double and single bonds are clearly distinct from each
other and their bond lengths very greatly (alternating long, short, long, etc.). However,
in ion B, all of the carbon-carbon bonds are very similar. Explain.
A
OH
+H-
B
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please answer the 2 questions please
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15) Under each structure, write "Node," "Linker," or "Neither" depending on what role (if any) that
structure can play in the construction of a MOF.
b)
но
OH
OH
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Confused about this work sheet. Can I get some help to compare my answers?
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Part G. Molecules with Oxygen and Nitrogen.
Organic molecules often contain the elements oxygen and nitrogen. Construct a model with the molecular
formula C5H12O where the oxygen is bonded to one hydrogen. When a hydrogen is bonded to an oxygen or
nitrogen, you need to draw that bond in a bond-line structure. Draw the bond-line structure of this model.
What is the molecular geometry of
oxygen in your structure?
Draw three more constitutional isomers with the molecular formula C5H12O where the oxygen is bonded to
one hydrogen.
Structure
Structure
Structure
Draw three more constitutional isomers with the molecular formula C5H12O where the oxygen is bonded to
two carbon atoms.
Structure
Structure
Structure
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a. Indicate yes or no whether the foltowing alkenes (written in condensed form here) would have cis-trans
jsomers?
b. In the following molecules rank the polarity of the bond indicated by the line (1= most polar, 4 = least
polar).
A
В
C
D
H3C-Br
H3C-OH
H3C-SH
H3C-CH3
c. Of the four hybridized atomic orbital energy diagrams drawn below, which best represents an sp
hybridized nitrogen atom?
A
D
E
2p
1 20
2p
2p
业生4
2s
1s
1s
1s
1s
1s
1s
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- The following bonds in vinyl alcohol, what is the bond angles for C-O-H? See the structure as your basis. ... нн H-c=c-ö-H A) 109.5° B) 90° c) 180° D) 120°arrow_forwardPlease solve thisarrow_forward8. a) State the hybridization (sp°, sp', sp) of each carbon in this molecule, going left to right. HC b) Write "most" under the most stable alkene. Write "least" under the least stable alkene. c) Write "most" under the most stable cation. Write "least" under the least stable cation. CH2 CH3 CH3 CH3 CH3 H3C CHT HC H3C ONLY roactions we have studied this semester.arrow_forward
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