Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.

com
Name:_________________________________ Due 09/11/20

Q1-Use your knowledge of functional groups and formal charges and draw Lewis structures for the
following condensed molecular formulas. Draw all the lone pairs and formal charges.

A) (CH3)2CHCH2CHO B) CH3CH2CHOHCH3 C) (CH3)4N+

D) NO3 E) CH3COOCH2CH3 F) CH3CON(CH3)2

Q2- Add lone pair of electrons on nitrogen oxygen where appropriate to complete their valence shell in
the molecules drawn below. Do not put lone pairs on carbons. Assign formal charges to the atoms
including carbons where appropriate.

A) B) D)
H O H H H H

H C C O H C O H C C C H

H H H H H H

C) H F)
H E) H
C O H H H
H C C
C H H
C H H C N C H
H C N C H
C
H C H H
C H C H
H H H
H H
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20
Q3- For the following molecules use this symbol to indicate the direction of bond dipole of all
polar bonds. If the molecule that have an over all dipole moment use an additional sign to
indicate the molecular dipole moment in the dotted box on the left side of the molecule.

A) B) C)
H F

H
C B H
C C N
H Cl F F
H
H

Consider CN (cyano group) as

D) a whole electronwithdrawing F)
H
NC CN

N C
H H C C
F F
H NC F
CN
E
G) H) I)

Cl O H

C C
H 3C CH 3 N H

Q4- In most amines the nitrogen atom is sp3 hybridized with a pyramidal structure and a bond angle of
109°. However, in formamide the nitrogen atom is planar with a bond angle close to 120°. Draw
resonance structures for formamide and explain with words why this unexpected bond angle occurs.

C H
H N

H
formamide

2
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20
Q5- Circle the functional group of each compound in the following structure. In the box state to which
class of compound the structure belongs to. Also indicate 1o, 2o or 3o where applicable. Do not circle or
label carbon-carbon double bonds (alkenes).
COOH
O
CHO

O
O
O

O
NH

CH3
H
O N OH

Q6- Complete the molecular orbital diagram of the formation of a carbon-carbon double bond. Fill in the
number of electrons in the molecular orbital. In the dotted box label and draw the cartoon
representation of the molecular orbitals.
Energy

C 2py C 2py

3
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20
Q7-Draw the next best contributing structure of each molecule in the space provided. For the structure
on the left, use arrows to indicate the movement of the electrons. Finally, if one of the two contributing
structures is the major contributing structure draw a circle around the major contributor.
O

H C H
C C
H
H H

H 3C

N C C H

H 3C

H C
C O
H
H

H O H

C C

H H

H H

H C C
C C H

H H
O

C
C H
C
H 3C

4
Name:________________________________ Due 09/11/20
Q8a) Drawn below are the 4 major resonance contributors for the molecule shown in box #1. Draw all
curved arrows to show the movement of electrons on molecule in box # 1 that would convert that
molecule to the molecule in box # 2. Now draw curved arrows on molecule in box # 2 to molecule in box
# 3. So, on and so forth.
Box #1 Box # 2
O O

N C N

O O

Box # 4 Box # 3
O O

N C N

H
O O

Box # 5

Q8b) Consider the resonance structures drawn above and circle the atoms that are electron source in
the molecule drawn below.

5
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20
Q9-For the following molecules write the hybridization state of all the C, N and O atom in each
molecules. Remember resonance effects hybridization.

A)
O B)
H
C
C CH2 CH 3
C H
H C O
CH 3 C
N
H
CH 3

C) D)
H
H2
H C C CH 3
C C N
CH2 H
C C CH 3 CH 3 C
H C H
O
H

E) F)
O O

C H C
O C N CH2
C
H H 2C CH2
C
H2

6
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20
Q10- Describe each bond indicated with an arrow as the overlap of orbitals. For example an answer
might be σCsp3-Csp3

σ
H
σ
H
σ H H 2C
C

CH2
H C HC
C C N
π
C C H 3C
σ
H N H

Nicotine
π

Q11- Many naturally occurring compounds contain more than one functional group. Circle all the
functional groups in the following compounds. You may circle the same group twice on the same
molecule.
O
COOH HO
O C
N
NH 2
C CH 3
H 2C N HO
H S CH 3

Dopamine
Neurotransmitter that is deficient
in Parkinson's disease
Penicillin G
Naturally occuring antibiotic
I OH

HO

I O
NH 2

Thyroxine O
thyroid hormone
I COOH Testrosterone
Male sex hormone

7
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20
Q12- Write the IUPAC name of the following molecules on the line provided.

______________________________________________________________________________

______________________________________________________________________________

______________________________________________________________________________

Q13- From the IUPAC name, draw the appropriate line angle drawing for the following alkane.
4-ethyl-5-isopropyl-2-methyloctane cis-1,2-Diethylcyclopentane

8
Produced with a Trial Version of PDF Annotator - www.PDFAnnotator.com
Name:________________________________ Due 09/11/20

Q14- Circle the structure that represents a conformation of 2, 2-dimethylbutane sighting along any C-C
bond. Circle all the correct answers.
H H
H 3C CH3 H 3C CH3

H H H 3C CH3
CH2CH3 H

A B

H CH(CH3)2
2,2-dimethylbutane H H
H 3C CH3

H CH3 H H
H H
D
C

Q15- Draw lowest and the highest energy Newman projections for 2,2-dimethylbutane looking down the
C2-C3 bond for the following molecules.

3
H 3C 2 CH2 CH3
C CH2
CH3
CH3

Highest Energy
Lowest Energy

9
Name:________________________________ Due 09/11/20
Q16- For each of the following molecule circle the one that is more stable. Justify your answer by
marking an X next to all the different kinds of strain present in the unstable molecule. When comparing
two different cyclic hydrocarbons consider the optimize conformation of the molecule for example chair
conformation for cyclohexane etc. Only when it states “planar” underneath the molecule compare the
planar structure.

Angle Strain Torsional Strain Steric Strain

H HH
H H
vs
H H HH
HH
H

vs

Br Br
H Br H H
vs
H H H H
H Br

vs
Planar
CH 3 CH 3

H 3C vs CH 3
CH 3
CH 3

vs

Convert the planar molecules into a chair

conformation to determine their relative stability

vs

10
Name:________________________________ Due 09/11/20
Q17-Draw the alternative chair conformations for the following cyclohexane derivatives. Indicate by a
label whether each alkyl group is axial or equatorial. When there is a difference in energy between the
two conformers, circle the more stable conformer? (For QC & D assume chlorine and methyl groups are
approximately of same size)

A)

B)

C)

Cl

D)

Cl

E)

11