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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10) 4-aminobenzoic acid (PABA) was one of the first ingredients used in the initial formulation of
sunscreen. Draw a mechanism (add curved arrows) converting resonance structure A into resonance
structure B (Note: lone pairs are not shown for resonance structure B).
11) Draw the intermediate observed in the following Lewis acid-catalyzed reaction.
12) Which nitrogen contains a delocalized lone pair of electrons (circle)?
13) Add curved arrows to the following molecules to convert them to their conjugate bases. Next to the
anion of the conjugate base, draw the expected counterion.
14) Basic red 1 is a tetracyclic compound (it has four rings) that is used as commercial dye. This
compound has many significant resonance structures and the positive charge is highly delocalized. While
resonance structures can be drawn in which the positive charge is spread throughout all four rings,
nonetheless, one of the rings likely bears very little of the charge relative to the other rings. For simplicity,
the positive charge has been shown in the center of the molecule.
a)
Circle the aromatic ring that is not participating as effectively in resonance and briefly suggest an
explanation.
b)
Draw three additional resonance structures and order them from most significant to least
signification. Only 1 of your structures may have a formal charge on a carbon.
Most-----------------------------------------------------Least
15) In the large boxes, below draw 4 constitutional isomers with the molecular formula C
₄
H
₈
O and place a
number in the smaller box ranking them from lowest boiling (1) to highest boiling (4). There are 2
conditions you must follow. 1) Each of the 4 must contain a different functional group, and 2) none of the
compounds may contain an alkene.
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Related Documents
Related Questions
2. Complete the table for the indicated compounds
Molecule
C2H2
SF5-
NO3-
Lewis structure
include lone pairs &
formal charges on each
atom
Resonance
structures
don't have to include
lone pairs; write N/A if
there are none
Electron Geometry
Hybridization
on central atom
Overlapping
orbitals
include value of n in the
orbital name (e.g. 1s, not
s). Write N/A if that kind
of bond is not present in
the molecule
T:
Molecular
Geometry
Bond angle(s)
include < as necessary
3D structure and
polarity
don't have to include
lone pairs; draw the
|dipole arrow on the
molecule or write "non-
polar"
arrow_forward
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
arrow_forward
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?
arrow_forward
Four major contributing resonance structures are possible for the given cation, which is the intermediate o complex of an
electrophilic aromatic substitution involving phenol and bromine. Two structures are given but are incomplete. Complete the
given structures by adding nonbonding electrons and formal charges. Draw the remaining structures (in any order), including
nonbonding electrons and formal charges.
Complete structure A.
Complete structure B.
: 0 H
:0-
Br :
Br
arrow_forward
Please answer only question 3
arrow_forward
8
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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_forward
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.
arrow_forward
5 please, if you can help with me with the other one.
thank
arrow_forward
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.
arrow_forward
Bond Angles in an Organic
Molecule II
The random letter labels in this diagram of allylcyanide are to
be associated with the corresponding bond angle (or other
property of the nearest atom).
H
H
H
dc
H-
a
H
b
C=N
Match the following (but do not select any individual letter
more than once):
CCC angle ~109.5°
HCH angle ~120º
CCC angle ~120°
HCH angle ~109.5°
bond angle ~180°
3.
3
3
•
arrow_forward
help
arrow_forward
Part B: Models
1. For each chemical formula given, draw the Lewis structure of each isomer that
approximates the actual shape and name following IUPAC rules. When requested,
give the hybridization of every central atom.
a) C4H10 (2 isomers)
abioe onimA (d
mol of ertio doss iw toss
anistur
b) C3H6CI2 (4 isomers)
arrow_forward
Draw a valid Lewis (electron dot) structure of the following molecular formula. Note multiple structures (isomers) possible you
only have to draw 1, but it must be valid (i.e. all atoms having the correct number of electrons). You must show how you arrived
at the answer so I know it was not just copied from Google Images. You must show your work when tallying bonding electrons
and how you get to the final structure to get credit!
C2H3N
arrow_forward
Oo.37.
Subject :- Chemistry
arrow_forward
Just need the last two, Bond angle and 3D structure and polarity
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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
arrow_forward
Please help wiith the fourth one (C3H8O)
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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
arrow_forward
If the symbol X represents a central atom, Y represents outer atoms, and Z represents lone pairs on the central atom,
the structure Y-X-Y could be abbreviated as XY,Z,.
Classify each molecule according to its shape.
Square
pyramidal
Linear
Bent ( 129) Bent ( 109)
Trigonal
T-shaped
See-saw
Square planar
pyramidal
Answer Bank
XY,Z2
XY,Z,
XY,Z
XY,Z;
XY,Z
XY,Z2
XY,Z
XY,Z
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None
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