Name ____________________________
Chem 7A
Quiz 4
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. (1 point each)
1) Which of the following will give the farthest downfield signal in a proton NMR spectrum?
A) -CH3
B) -CHO
C) -CH2OH
D) -CH=CH2
1)
E) -CH2Cl
2) Which of the following structures is consistent with the following data:
IR: sharp band at 3080 cm¯1
sharp band at 1640 cm¯1
sharp bands at 915 and 995 cm¯1
A)
B)
proton NMR:
triplet
quintet
triplet
multiplet
C)
D)
2)
3H
2H
2H
1H
= 1.0 ppm
= 2.0 ppm
= 5.0 ppm
= 5.6 ppm
E)
3) The 1 H NMR spectrum of the following molecule would appear as:
3)
A) two singlets and two doublets
B) two singlets and two overlapping multiplets
C) two doublets and two overlapping multiplets
D) one singlet, one triplet, and one multiplet
E) too complicated to be useful
4) Which of the following structures is consistent with the following data:
IR: sharp band at 2900 cm¯1
sharp band at 2120 cm¯1
A)
B)
4)
(there are no bands above 2900 cm¯1 )
C)
D)
1
E)
5) The IR spectrum shown below matches which of the following compounds?
5)
A) 1-pentyne
B) pentane
C) 2-pentyne
D) 2-pentanone
E) 1-pentanol
FREE RESPONSE. Write your answer in the space provided.
6) How many different chemical shifts are expected for each of the following molecules? (3 pts)
a)
b)
1H
_____
13C
1H
_____
d)
c)
13C
_____
_____
e)
1H
_____
13C
_____
1H
_____
13C
_____
1H
_____
13C
_____
f)
1H
13C
_____
2
_____
7) Label each of the following sets of hydrogens as a singlet, doublet, etc. Assume the N+1 rule holds true. (2 pts)
8) Predict the structure of the molecule that has the following 1H NMR spectrum. The molecular formula is C5H12O (2 pts)
Structure:
_________________________________
3
9) Draw a correct structure or provide a correct name for each of the following: (1 pt each)
a)
c)
2-cyclopenten-1-ol
b) (Z)-4-bromo-3-methyl-3-octen-1-yne
d)
4