Answers to Hour Examination #1, Chemistry 225/227 - 2013

1.
H

H3C

CH3
H3C

CH3

CH2
H3C

CH2

CH3

CH3

H3C

CH2
CH3

Note the double bond character in the resonance form. Double bonds are (much)
shorter than single bonds, and so the resonance hybrid shows a contraction from
1.50 to 1.43 .
Alternatively, a good answer might just note that the filled (sigma CH) empty (2p)
overlap gives double bond character to the C-C bond and shortens it.
2. The first reaction transfers negative change from the relatively
electronegative oxygen to the relatively electropositive carbon. Bad.
HO
HO

H2C

CH2

H2C

CH2

O
HO

H2C
CH

CH3

H2C

CH3

CH

HO

1
In the second example, but not in the first,
the ion formed is stabilized by resonance.

O
H2C
HO

C
H

CH3

(b) The newly formed C-C sigma bond is worth about 90 kcal/mol and the broken
pi bond is worth about 66 kcal/mol, so the reaction is exothermic by about 20
kcal/mol.

(c)
H

There is another resonance form. In the combination, each bond is 1/2 single, 1/2
double.
The result is the average of 1.33 and 1.47, just about 1.39

(d) The cis molecule has 5 different carbons, but the trans molecule has only
four. It is cis.
1
4

3
5

1
4

3
4

3.

4.
A and C go up in energy as two 1,2 bonding interactions weaken, becoming A-R
and C-R. In B and D antibonding interactions weaken, and the energy comes
down as B-R and D-R are formed.

+
+

Energy

D-R
+

C-R

+
+

+ +

nonbonding

B-R
+
+

A-R

+
+

+ +
+ +

H H
H H

H
H

2+

+
+

H
H

As there are only two electrons in square H4 , it must be square (electrons in

lower energy orbital, A vs. A-R).

5a
H

H
N

b.

H
N

H
H

H
ii

i
c.
H

iii

H
N

anti
2

d. A planar hydrazine would require sp nitrogens. Their lone pairs would reside
in aligned p-orbitals, which is energetically destabilizing as electrons are forced
into an antibonding orbital.

Np

Np
H

N
H

N
H