Homework - Review of Chem 2310
Name ____________________________________
1. Fill in the following partial Periodic Table of Table of Elements. Do as much as you can from memory.
2. Using the Table above, circle the more electronegative atom in each pair.
a) nitrogen oxygen
d) carbon
nitrogen
b) carbon
e) oxygen
fluorine
hydrogen
c) chlorine carbon
f) carbon
oxygen
3. What is an isotope?
4. Give the number of valence electrons of each of the following elements.
a) oxygen
f) nitrogen
k) boron
b) hydrogen
g) iodine
l) sulfur
c) chlorine
h) carbon
m) magnesium
d) lithium
i) sodium
n) phosphorus
e) bromine
j) aluminum
o) potassium
5. Draw the Lewis structure for each of the following elements, and tell how many covelent bonds you
would expect each to form (no charges).
a) carbon
c) oxygen
e) bromine
g) sulfur
b) nitrogen
d) hydrogen
f) phosphorus
h) chlorine
HW Review p 2
6. Draw complete Lewis structures for three compounds with the formula C2H5NO (and no charged atoms).
7. Give the molecular formula for the following line structures.
b)
a)
NH2
O
c)
d)
N
Br
8. Give the unsaturation number for each of the following molecular formulas, and draw one possible
structure for each.
a) C5H10O
b) C5H12O
c) C5H11N
d) C5H8O2
9. Give the geometry of all atoms (except hydrogen) in each of the following compounds.
O
a)
c)
b)
H
N
O
N
d)
OH
HW Review p 3
10. Label the polar bonds in each of the following molecules (ignore C-H bonds) using partial charges
(!+, !-) or polarity arrows.
O
b)
a)
Br
O
c)
d)
O
Cl
H
11. Give the hybridization of each atom (except hydrogen) in the following compounds.
O
a)
b)
H
N
c)
O
OH
N
d)
12. Label each molecular orbital and give the atomic orbitals that it came from in the following compound.
d e
a)
f)
N
a
Br
i
b
c O
h
f g
b)
g)
c)
h)
d)
i)
e)
13. Draw resonance structures for the following compounds, using arrows to show where the electrons go.
O
a)
O
HW Review p 4
b)
14. Give the charge next to each atom in the following compounds which has a charge.
a)
b)
O
H
d)
O
O
e)
H
c)
NH
f)
NH
15. Give all functional groups which the following compounds contain.
O
O
OH
a)
O
c)
b)
H
NH2
O
N
O
d)
Cl
O
e)
Cl
16. What functional groups do the following compounds contain?
a) 2-pentyne
b) 2-pentanone
c) trans-2-pentene
d) methyl pentanoate
e) pentanal
f) 2-cyanopentanoic acid
g) 2-pentanol
h) 2-pentanamine
O
O
f)
HO
N
H
HW Review p 5
17. Which intermolecular force will be the most important in the the following compounds?
a)
OH
c)
b)
O
H
O
d)
f)
e)
N
Br
OH
18. Choose the compound in each pair which will have the highest boiling point, and briefly explain your
choice.
a)
b)
OH
c)
d)
OH
O
NH2
e)
NH
19. Choose the compound in each pair which will be the most soluble in water, and briefly explain your
choice.
a)
b)
c)
NH2
O
O
OH
O
HW Review p 6
20. Assign each of the following IR's with one of the compounds shown (not all compounds will be used).
O
A
C
B
D
OH
OH
N
E
F
___
___
___
___
___
___
G
O
H
NH2
HW Review p 7
21. Give the relationship between each of the following compounds (identical, constitutional isomers,
enantiomers, diastereomers, meso, not isomers).
b)
a)
NH2
NH2
d)
c)
e)
OH
OH
OH
OH
f)
Cl
h)
g)
Cl
22. Draw correct line structures for the following compounds.
a) 3-ethylhexane
b) 1-chloro-1-methylcyclopropane
d) (R)-2-bromopentane
g) 2-cyclopropylbutane
e) 3-methyl-4-penten-1-yne
h) cyclononyne
c) (Z)-3-methyl-2-pentene
f) bicyclo[0.3.4]nonane
i) (trans)-1,3-hexadiene
HW Review p 8
23. Give correct names for the following structures.
a)
b)
Br
c)
d)
e)
f)
24. Circle the stronger acid in each pair, and briefly explain your choice.
a)
OH
SH
b)
OH
OH
c)
OH
d)
OH
Cl
e)
NH2
OH
25. Draw the Fischer projection for the following compound.
OH
OH
O
HO
H
OH
OH
HW Review p 9
26. Draw a chart showing the chemical shift, integration, and splitting for each of the following spectra.
Then deduce their structures.
C7H12O3
a)
C8H10O
b)
27. Choose the correct answer.
a) If the Keq is >1, the reaction is (favorable / unfavorable).
b) If the !G is > 0, the reaction is (favorable / unfavorable).
c) If you take away a product from a reaction at equilibrium, more (products / reagents) will be
formed.
d) If you heat a reaction, the rate will (increase / decrease).
e) If you increase the concentration of a reagent which is in the rate limiting step, the reaction rate
will (increase / decrease).
HW Review p 10
28. Write the pKa of the acid on each side of the equation below it; then, use them to predict whether the
products or reactants will be favored by the equilibrium.
a)
+ H2SO4
O
+ HSO4-
O
H
+ NaOH
b)
Na+
O
O
c)
+ H2O
OH
+ NaHCO3
O
Na+ + H2CO3
29. What is an electrophile?
30. What is a nucleophile?
31. What is the difference between a base and a nucleophile?
32. Label the following as nucleophiles or electrophiles.
b)
a)
d)
g)
CH3Br
Br
e)
h) CH3+
Na+
c)
CH3OH
f)
Br2
i) CH3O-
HW Review p 11
33. Using your knowledge of nucleophiles and electrophiles, draw arrows to show how the following
species will react with each other (1st step only) and give the immediate product.
Br
a)
O
b)
Br
Br
c)
H
Br
(cold, dark)
Br
d)
34. Draw the complete mechanisms of the following reactions.
a) methane + bromine + heat or light
b) ethyl bromide + sodium hydroxide
c) tert-butyl iodide + sodium ethoxide
methyl bromide + HBr + byproducts
ethyl alcohol + sodium bromide
2-methyl-1-propene + ethanol + sodium iodide
HW Review p 12
d) cyclopentene + sulfuric acid + water
cyclopentyl alcohol
35. Give all products of the following reactions (except stereoisomers of chiral compounds).
HCl
a)
NaOH
b)
Br
c)
Br2
2 eq HCl
d)
O
e)
Na
Cl
f)
O3
H2O2
KMnO4
g)
H2O, NaOH
h)
HCl
HW Review p 13
i)
NaI
acetone
Br
j)
Na, NH3
H2SO4, Hg(OAc)2
k)
H2O
1. BH3-THF
l)
2. H2O2, NaOH
S
m)
Na
Cl
SH
HBr
n)
CH3OOCH3
Br2
o)
p)
OH
Br
q)
r)
s)
heat
1. Hg(OAc)2, H2O
2. NaBH4
H2, Pd/C
HNO3
H2O
HW Review p 14
1. O3
t)
2. (CH3)2S
(CH3)3COK
u)
Br
KMnO4
v)
H2O, NaOH
O3, H2O
w)
H2, Pt/C
x)
1. disiamylborane
y)
2. H2O2, NaOH
I2, H2O
z)
aa)
NaCN
Cl
Br
2 eq NaNH2
Br
bb)
2. H2O
O
cc)
dd)
Ph
O
O
H
2 eq Br2
HW Review p 15
H2, Lindlar
ee)
Cl
2 eq NaNH2
ff)
2. H2O
Cl
36. Write a reaction sequence (starting materials, reagents, and products for each step) by which the
following transformations could be accomplished.
a)
O
Cl
b)
(2 steps)
OH
H
H
O
O
c)
d)
(3 steps)
(3 steps)
(2 steps)