CHM 2211C Exam I Summer 2024 — 100 points Name: W By
Measurable Course Objectives Addressed in this Exam
» Write products and complete stepwise mechanisms for the reactions and synthesis of alcohols.
¢ Analyze and interpret IR, NMR, UV/Vis and mass spectra.
Provide a logical and realistic set of reactions that will convert a given starting material to a desired end
product.
The total point value for this exam exceeds 100 points. The extra points are extra credit. It is possible to achieve
an exam grade of over 100 points or greater than 100%.
Directions: For the following multiple choice questions, choose the most correct answer-.
1) (1.5 pts) Absorption of what type of electromagnetic radiation results in excited rotational states?
a. X-rays
b. radio waves
c. ultraviolet radiation
d. ) microwaves
e. infrared radiation
2) (1.5 pts) Which region of the electromagnetic spectrum has the lowest encrgy per photon?
a. infrared radiation
b. microwave
@ radio waves
d. ultraviolet radiation
e. visible
3) (1.5 pts) How many units of unsaturation are associated with the molecular formula CoHoFIN3O,?
4) (1.5 pts) Which of the following statements best explains the information gained from a mass spectrum?
a. Itallows the determination of the number of protons in a compound.
b. It allows the determination of the kinds of functional groups in a compound.
(c.) It allows the determination of the molar mass and the mass of some fragments of a compound.
d. It allows the determination of the presence and nature of a carbocation in a compound.
e. It allows the determination of the presence and nature of a free radical in a compound.
, 5) (1.5 pts) '"H-NMR nuclei located near electronegative atoms tend to be relative to 'H-NMR nuclei
which are not.
a. shielded
(b, deshielded
c. resonated
d. split
e. None of the above.
6) (1.5 pts) Which of the following compounds would show a strong absorption in its infrared spectrum
between 1100 and 1200 cm™!? <-o
CH o " C/O
HBC/\(
CHy 3
HiC /U\/\
CHy Hi” SNH CHy HNT
> NH, 3 \©\
cl
a b c d @
7) (1.5 pts) Using a 60-MHz NMR spectrometer, the protons of chloromethane appear at 3.05 ppm. When
the same sample is placed in a 100-MHz NMR instrument, where does the signal appear?
a. 4.88 ppm
@ 3.05 ppm
c. 1.83 ppm
d. 1.22 ppm
e. It cannot be determined from the above information.
8) (1.5 pts) Which structure is consistent with the infrared spectrum shown below?
. | c2n 1
J ] cze
L2 '
| | L |
! 2246 -
2079 ' 164y ©=C oe
perns ot 000 1000 1200 +0
HSC/Y O\ CH, i //N CH4 .
H3C/\H/\CH3 O\ ‘/__< @/ Hac/‘\‘(
o CH, HsC CH, a
a b c @ e
Measurable Course Objectives Addressed in this Exam
» Write products and complete stepwise mechanisms for the reactions and synthesis of alcohols.
¢ Analyze and interpret IR, NMR, UV/Vis and mass spectra.
Provide a logical and realistic set of reactions that will convert a given starting material to a desired end
product.
The total point value for this exam exceeds 100 points. The extra points are extra credit. It is possible to achieve
an exam grade of over 100 points or greater than 100%.
Directions: For the following multiple choice questions, choose the most correct answer-.
1) (1.5 pts) Absorption of what type of electromagnetic radiation results in excited rotational states?
a. X-rays
b. radio waves
c. ultraviolet radiation
d. ) microwaves
e. infrared radiation
2) (1.5 pts) Which region of the electromagnetic spectrum has the lowest encrgy per photon?
a. infrared radiation
b. microwave
@ radio waves
d. ultraviolet radiation
e. visible
3) (1.5 pts) How many units of unsaturation are associated with the molecular formula CoHoFIN3O,?
4) (1.5 pts) Which of the following statements best explains the information gained from a mass spectrum?
a. Itallows the determination of the number of protons in a compound.
b. It allows the determination of the kinds of functional groups in a compound.
(c.) It allows the determination of the molar mass and the mass of some fragments of a compound.
d. It allows the determination of the presence and nature of a carbocation in a compound.
e. It allows the determination of the presence and nature of a free radical in a compound.
, 5) (1.5 pts) '"H-NMR nuclei located near electronegative atoms tend to be relative to 'H-NMR nuclei
which are not.
a. shielded
(b, deshielded
c. resonated
d. split
e. None of the above.
6) (1.5 pts) Which of the following compounds would show a strong absorption in its infrared spectrum
between 1100 and 1200 cm™!? <-o
CH o " C/O
HBC/\(
CHy 3
HiC /U\/\
CHy Hi” SNH CHy HNT
> NH, 3 \©\
cl
a b c d @
7) (1.5 pts) Using a 60-MHz NMR spectrometer, the protons of chloromethane appear at 3.05 ppm. When
the same sample is placed in a 100-MHz NMR instrument, where does the signal appear?
a. 4.88 ppm
@ 3.05 ppm
c. 1.83 ppm
d. 1.22 ppm
e. It cannot be determined from the above information.
8) (1.5 pts) Which structure is consistent with the infrared spectrum shown below?
. | c2n 1
J ] cze
L2 '
| | L |
! 2246 -
2079 ' 164y ©=C oe
perns ot 000 1000 1200 +0
HSC/Y O\ CH, i //N CH4 .
H3C/\H/\CH3 O\ ‘/__< @/ Hac/‘\‘(
o CH, HsC CH, a
a b c @ e
