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

sp2 N
sp2

sp3
sp2
6) O

sp2
sp
sp sp3
7) Draw H2NCH2+ in its second best resonance structure.

H H H
N CH2 N CH2
N CH2
H H
H

8) Draw the best Lewis structure for CH3CHO, a neutral molecule

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 left-
hand 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

Cl
Cl Cl

4 2
3
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.
a) FC = 5 – (4 + (1/2(4))) = -1
N

b) FC = 5 – (2 + (1/2(6))) = 0
N N

FC = 5 – (0 + (1/2(8))) = +1
Draw the Lewis structure.
H
a) (CH3(OH2)) +
H C O H

H H
H

H C N
b) CH3NO2 O

H O

Draw all possible isomers of C2H4O.

O
O
HO C CH2
C H
H3C H H2 C CH2
Are each of the following pairs isomers or resonance structures?
a) H3C CH3
H3C CH2
C
H2 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.
a) O O

H NH2
H NH2

b) O
O

H3C C C CH2
H3C C C CH2 H
H
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
a) C CH3
H3C C
H2

tetrahderal

b) CH2

H3C OH

Trigonal planar
Draw the three dimensional structure of the following.
H
a) CH3OH H

C H
O
H

b) (CH3)2NH
H H
H H

C
N H
H
H
Convert each molecule into a skeletal structure.
a) (CH3)2CHCH2CH2CH(CH3)2

H H
b) H H
H
H3C C C
CH3
CH
H
H H H3C
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

b) sp2
CO2H

sp
Which is the weakest of the indicated bonds?

a b
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
b
HO a

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 CH3
+ HO
OH
O
A B CA
CB

+ NH3
+ NaNH2
H Na
CB CA
A B
Draw the products and determine if the reaction occurs.

O O

+ O CH2CH3 + HO CH2CH3
F3C OH F3C O
pka=0.2 pka=16
Products favored

O O
NaCl + HCl
+

OH O pka=-7
pka=5 reactants favored
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
H c
a H H

C is the most acidic hydrogen b/c it’s

bonded to an sp hybridized carbon.
Draw the products of each reaction and label the starting materials
as a Lewis acid and base.
Cl Cl
Cl +
B Cl B Cl

LB Cl Cl
Cl
LA
Cl Cl
Cl
O + B
B
O
Cl Cl Cl
LB LA
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
O
OH H
H +
H
O
K
O
3)
O
H H OH + OH
O

4) Choose the strongest acid.

S
H Cl H Br H
H

Both Cl and Br are further right than S.

H Br And Br is further down than Cl. So most
acidic.
5) PH2 SH
OH

SH
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 SH CH3

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 SiH3 CH3

3 2 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 O
H2 H2
H3C C OH H3C C OH

Cl Br
2 3
O O

H2 H2 H2
H3C C OH H3C C C OH

1 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 H
N H H N

H H

11)
O
O
H
O
O
N NH
1) Draw an aldehyde.
O
RCHO

R H

2) Draw an ester.

O
RCOOR
R
or
R O
RCO2R
3) Draw a sulfide.
S RSR
R R

4) Draw 1,1-dimethylcyclohexane.
5) Draw 2,2,4-trimethylhexane.

6) Draw trans-1,3-dibromocyclobutane.
Br

Br H

H Br
Br
Br
H Br

Br H
Br
7) Draw cis-1-chloro-3-isopropylcyclopentane.

Cl
Cl

Cl H
H

H H Cl

8) Draw sec-butylcycloheptane
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 H

Cl Cl Cl H

H H Cl H

anit 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

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
FC = 4 – (2 + (1/2)(6)) = -1
H C

H
 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 O
  H

7) Which molecule plays the role of acid?

 
HNO3 + H2SO4 → HSO4– + H2NO3+
  acid
8) Using pKa values from the table, determine if the following
reaction will occur.
O
pKa HA + NaOCH3
3.7 HCOOH
OH
4.2 C6H5COOH 4.75
4.75 CH3COOH O

15.5 CH3OH HO CH3 +

O
15.5
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
+ CH3

E 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
H H Br
H H H
H H
H
H H H
H H

More stable
Using Newman projections, draw all the staggered conformations
of 1-chloropropane, label the anti and gauche forms.
1
2 Cl