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Organic Chemistry I: Lewis Structures, Hybridization, and Resonance, Lecture notes of Organic Chemistry

Morton CollegeOrganic Chemistry

Draw a Lewis dot structure for each anion. For anions that can resonate, draw all relevant resonance structures. For each compound, indicate which atoms the ...

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Organic Chemistry I
CHEM 2323
Packet #1
1. Draw a Lewis dot structure for each of the following condensed structural formulas.
What is the hybridization of each carbon atom in each structure?
Rank the compounds by molecular dipole.
(CN)2CC(CN)2CH3CN CH3C(NH)CH3
C C
C
C
C
C
N
NN
N
C C N
H
H
HCC
N
C
H
H H
H
H H
H
C C
C
C
C
C
N
NN
N
C C N
H
H
HCC
N
C
H
H H
H
H H
H
sp
sp2
sp3
sp2
sp
sp
sp2
sp3sp3
(CN)2CC(CN)2CH3CN CH3C(NH)CH3
highest dipole middle dipole
lowest dipole
(zero dipole)
pf3

Partial preview of the text

Download Organic Chemistry I: Lewis Structures, Hybridization, and Resonance and more Lecture notes Organic Chemistry in PDF only on Docsity!

Organic Chemistry I

CHEM 2323

Packet

1. Draw a Lewis dot structure for each of the following condensed structural formulas.

What is the hybridization of each carbon atom in each structure?

Rank the compounds by molecular dipole.

(CN)

2

CC(CN)

2

CH

3

CN

CH

3

C(NH)CH

3

C C

C

C

C

C

N

N N

N

C C

N

H

H

H

C

C

N

C

H

H H

H

H H

H

C C

C

C

C

C

N

N N

N

C C N

H

H

H

C

C

N

C

H

H H

H

H H

H

sp

sp

2

sp

3

sp

2

sp

sp

sp

2

sp

3

sp

3

(CN)

2

CC(CN)

2

CH

3

CN

CH

3

C(NH)CH

3

highest dipole middle dipole

lowest dipole

(zero dipole)

2. Consider the following anions

Draw a Lewis dot structure for each anion. For anions that can resonate, draw all relevant

resonance structures.

For each compound, indicate which atoms the negative charge can be located.

What is the hybridization of the atom(s) the negative charge is located?

Draw the conjugate for each anion.

Rank the anions by stability.

resonates between resonates between no resonance resonates between

carbon and oxygen two carbons two oxygens

Rank the conjugates by acidity.

most stable anion after deprotonation results in most acidic conjugate

CH

3

CH

2

CH

2

CH

2

=CHCH

2

CH

3

C(O)CH

2

CH

3

CO

2

C

C

O

C

H

H H

H

H

C

C

C

H

H

H

H

H

C

C

C

H H

H

H H

H

H

C

C

O

O

H

H H

C

C

O

C

H

H H

H

H

C

C

C

H

H H

H

H

O

C

C

C

H

H

H

H

H

C

C

C

H

H

H

H

H

C

C

O

O

H

H H

C

C

O

H

H H

O

no resonance

sp

2

sp

2

sp

2

sp

3

H

3

C

O

CH

3

H

2

C

CH

3

H

3

C CH

3

H

3

C

O

OH

C

C

O

C

H

H H

H

H

C

C

C

H

H

H

H

H

C

C

C

H H

H

H H

H

H

C

C

O

O

H

H H

H

3

C

O

CH

3

H

2

C

CH

3

H

3

C CH

3

H

3

C

O

OH