Draw the resonance structure indicated by the arrows.
1)
2)
O
O
3)
O
O
Label each atom with the correct hybridization.
4)
sp3
sp3
HO
sp3
sp3
O
sp3
sp3
5)
sp3
N
sp2
sp2
sp3
sp2
6)
O
sp
sp
sp2
sp3
7) Draw H2NCH2+ in its second best resonance structure.
H
H
N
CH2
H
N
H
CH2
H
N
CH2
H
8) Draw the best Lewis structure for CH3CHO, a neutral molecule
O
C
H3C
H
9) Draw the Lewis structure for CH3COOH, a neutral molecule.
O
C
H3C
OH
10) Draw the Lewis structure for N2H2, a neutral molecule.
HN
NH
11) Draw in the electron flow arrows in on the left hand structure
that lead to the resonance structure on the right.
O
O
12) In the empty box, draw the best resonance structure of the lefthand compound, and draw one or more electron-flow arrows on the
preexisting structure that lead to the new structure.
O
O
13)
O
O
14)
Cl
Cl
Cl
Cl
Cl
1
Cl
Cl
Cl
4
3
2
Label each of the following as an ionic or
covalently bonded compound.
a) NaF
ionic
b) BrCl
covalent
c) NaOCHe
ionic
Calculate the formal charge of nitrogen in each of the following
compounds.
FC = 5 – (4 + (1/2(4))) = -1
a)
N
b)
N
N
FC = 5 – (2 + (1/2(6))) = 0
FC = 5 – (0 + (1/2(8))) = +1
Draw the Lewis structure.
H
a) (CH3(OH2))+
H
H
b) CH3NO2
C
O
H
H
H
C
N
H
O
H
O
Draw all possible isomers of C2H4O.
O
HO
C
H3C
H
C
H
O
CH2
H2C
CH2
Are each of the following pairs isomers or resonance structures?
a)
H3C
CH3
H3C
C
H2
CH2
C
H2
Neither, different formulas
b)
O
O
Isomers, same formula but
different arrangement of atoms.
Draw a resonance structure of each, and identify which is the major
contributor.
O
a)
H
b)
O
NH2
H
NH2
O
O
H3C
C
C
H
CH2
H3C
C
C
H
CH2
Draw all possible resonance structures of the compound below
and it’s resonance hybrid.
CH2
CH2
CH2
CH2

CH2
CH2



Predict the geometry around each indicated atom.
H2
C
a)
H3C
CH3
C
H2
tetrahderal
CH2
b)
H3C
OH
Trigonal planar
Draw the three dimensional structure of the following.
a) CH3OH
H
H
C
H
O
H
b) (CH3)2NH
H
H
H
H
C
H
N
H
H
Convert each molecule into a skeletal structure.
a) (CH3)2CHCH2CH2CH(CH3)2
H
b)
H
H
H
H
H3C
C
C
CH
H
H
H
H3C
CH3
Convert into Lewis structures.
a) (CH3)3COH
CH3
H3C
O
H
CH3
b) CH3COCH2Br
H
O
H
H
Br
H
H
What is the hybridizatio of th eindicated atom.
a)
sp3
sp2
sp2
b)
CO2H
sp
Which is the weakest of the indicated bonds?
b
a
c
A is the weakest bond due to it being composed
of a sp3 and sp2 hybridized orbital, thus having the
least amount of S character
NH2
HO
a
b
B is the weakest, b/c bond strength increases across a row
in the periodic table and N is to the left of O.
Draw the products and label each part.
O
O
OCH3
+
+
OH
O
A
B
CA
CB
+
H
A
CH3
HO
+
NaNH2
B
CB
Na
NH3
CA
Draw the products and determine if the reaction occurs.
O
O
+
F3C
O
+
CH2CH3
OH
F3C
pka=0.2
pka=16
O
+
NaCl
+
O
OH
reactants favored
CH2CH3
O
Products favored
O
pka=5
HO
HCl
pka=-7
Which is the strongest base?
HBr, HCl
or HF
HF, b/c it is the weakest acid.
Identify the most acidic hydrogen.
H
H
b
c
H
a H
C is the most acidic hydrogen b/c it’s
bonded to an sp hybridized carbon.
H
Draw the products of each reaction and label the starting materials
as a Lewis acid and base.
Cl
Cl
Cl
+
Cl
B
LB
Cl
Cl
Cl
LB
Cl
Cl
LA
O
B
Cl
Cl
+
B
B
Cl
Cl
LA
O
Cl
1) Complete the following acid-base reaction.
H
O
O
+
O
OH
+
2) Complete the following acid-base reaction. Draw only the organic
products.
KOH
OH
H
OH
+
O
O
H
O
H
K
3)
O
H
H
OH
O
+
OH
4) Choose the strongest acid.
H
Cl
H
Br
H
S
H
H
Br
Both Cl and Br are further right than S.
And Br is further down than Cl. So most
acidic.
5)
SH
SH
PH2
OH
Both O and S are further right than P. And
S is further down than O. So most acidic.
6) Choose the weakest acid.
OH
CH3
SH
CH3
C is further left than O and S so weakest
acid.
7) The following compound has two stereoisomers. One has a dipole
of 0 D, and the other has a dipole moment of 2.95 D. Draw the
structure of the stereoisomer with dipole moment of 2.95 D.
Cl
Cl
Cl
H
Cl
Cl
H
Cl
H
H
Cl
H
Cl
Cl
H
Cl
H
H
8) Rank the three compounds from least acidic (rank 1) to most.
OH
3
SiH3
2
CH3
1
We know Si is more acidic than C because it is below C in the
same column. Although Si and O can’t be compared directly, O is
much more acidic.
9) Rank the following compounds from most acidic (rank 1) to
least.
O
H3C
H2
C
O
OH
H3C
Cl
H2
C
OH
Br
3
2
O
O
H3C
H2
C
1
OH
OH
H3C
H2
C
H2
C
OH
4
Acidity is based on the electron withdrawing effect of the four
different substituents. O is the most electronegative, furthest up and
to the right, and thus gives the most acidic compd. And Cl is more
electronegative than Br b/c electronegativity increases up the
column.
10) Draw the electron-flow arrows that lead from starting materials
to products in this acid–base reaction.
H
H
H
N
H
H
H
H
H
11)
O
O
H
O
N
N
NH
O
1) Draw an aldehyde.
O
RCHO
R
H
2) Draw an ester.
O
R
R
O
RCOOR
or
RCO2R
3) Draw a sulfide.
S
R
RSR
R
4) Draw 1,1-dimethylcyclohexane.
5) Draw 2,2,4-trimethylhexane.
6) Draw trans-1,3-dibromocyclobutane.
Br
H
Br
H
Br
Br
Br
H
Br
Br
Br
H
7) Draw cis-1-chloro-3-isopropylcyclopentane.
Cl
Cl
Cl
H
H
H
8) Draw sec-butylcycloheptane
H
Cl
9) Draw 2,2,4,4-tetramethylhexane
10) Draw the structural formula of an alkane that has eight
carbons and only primary hydrogens.
CH3
CH3
H3C
CH3
CH3
CH3
Primary hydrogens are attached to carbons attached to only
one other carbon.
11) Draw the conformation favored by 1,2-dichloroethane at
equilibrium in the liquid phase by following this procedure.
H
H
H
Cl
Cl
H
anit
H
Cl
H
H
Cl
H
gauche
The gauche conformer is favored in the liquid phase due to a
polar effect. However, for this class I would accept the anit
conformer as your answer, which would be correct if in the gas
form.
12) Draw cis-3-ethyl-1-isopropylcyclohexane in its lowest energy
conformation
H
H
13) Draw trans-1-bromo-3-methylcyclohexane in its lowest energy
conformation
Br
H
H
CH3
1) Draw the Lewis structure of HNO3.
O
HO
N
O
2) What is the formal charge of the following compound?
H
H
C
H
FC = 4 – (2 + (1/2)(6)) = -1
O
3) Draw all resonance structures
O
O
O
O
4) What are the hybridizations of the numbered carbons?
sp3
1
2
sp2
5) Which of the following compounds has the largest net
dipole? Draw the contributing dipoles of the compound you
choose.
CO2
H2O
CHCl3
O
H
H
6) Draw the product of the following reaction. (Label the Lewis
Acid and Base)
LA
LB
7) Which molecule plays the role of acid?
HNO3 + H2SO4 → HSO4– + H2NO3+
acid
O
H
8) Using pKa values from the table, determine if the following
reaction will occur.
pKa
HA
3.7
HCOOH
4.2
C6H5COOH
4.75
CH3COOH
15.5
CH3OH
O
+
NaOCH3
OH
4.75
O
HO
CH3
15.5
+
O
pKa of the conjugate acid is larger than that of the acid so the
reaction favors the products.
9) Which is the strongest base?
LiOH
LiF
LiCH3
LiCH3 is the strongest base because the acid it forms when the anion is
protonated is very weak.
10) What intermolecular forces does the following molecule
exhibit?
O
O
It possesses Van der Waals and dipole-dipole interactions.
11) Which of the following has the highest boiling and why?
CBr3CH3
CH3OCH3
CH3NH2
CH3NH2 has the highest boiling point because it possesses the same
intermolecular forces as the first two molecules, but also has
hydrogen bonding capabilities.
12) Label the electrophile and nucleophile. Then if the reaction
occurs, draw the products.
O
O
+
E
CH3
Nu
13) Name the following compound.
2-sec-butyl-4-ethyl-1-methylcyclohexane
14) Which of the following has the highest melting point? Why?
a) 2-methylbutane
b) 2,2',3-dimethylbutane
c) 2,2',3,3'-tetramethylbutane
c) 2,2',3,3'-tetramethylbutane has the highest metlign point due to
its high symmetry giving it the ability to pack close together in the
crystal lattice.
15) Draw 2-chloro-4-ethyl-3-methylheptane
Cl
Draw the most stable form of trans-1-bromo-3-ethylcyclohexane.
H
Br
H
H
H
H
H
H
Br
H
H
H
H
H
H
H
H
H
H
H
H
More stable
H
Using Newman projections, draw all the staggered conformations
of 1-chloropropane, label the anti and gauche forms.
1
2
Cl