Chapter 1 - Structure and Bondin1!

1. Give the ground-state electron configuration for carbon (atomic number 6).

Answer: li2s22PX12p/ or li2i2p2

2. Give the ground-state electron configuration for fluorine (atomic number 9).

Answer: li2s22p/ 2p/2p/ or Is22i2/

3. Give the ground-state electron configuration for magnesium (atomic number 12).

Answer: li2i2p63i

4. How many electrons does silicon have in its valence shell?

Answer: four

Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots and show all
non-bonding electrons.
..
:CI:
5. C2Cl4 tetrachloroethylene Answer: :Cl:C::C.:C.l:
~.:Ql: ..

6. CO2 carbon dioxide Answer: :o::c::o:

.. ..
7. C~o methanol
H
Answer: H:C:O:H
.. ..
H
8. The structure of urea is shown below. Fill in any non-bonding valence electrons that are missing ITom the
line-bond structure.

0
" NH2
H2N- C-
:0:
Answer: .. II ..
H2N- C- NH2

9. The structure of urea is shown below. The carbon atom in urea is:
0
" NH2
H2N- C-
a. sp3 hybridized
b. sp2 hybridized
c. sp hybridized
d. not hybridized

Answer: b. Sp2 hybridized

Test Items for McMurry's Organic Chemistry, Seventh Edition I

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10. The structure of urea is shown below. The predicted NH2-C=0 bond angle in urea is:
0
II
H2N- C- NH2

a. 109.50
b. 1200
c. 1800
d. not predictable

Answer: b. 1200

Determine the hybridization for the indicated atoms in each structure below.
11.~ 13. 14.

CH3- CH2- c-
:0:
II ..JI.
2-
/12.
H
\CH3-\c= N:
11. The hybridization ofthis oxygen atom is - .

Answer: Sp2

12. The hybridization of this oxygen atom is -.

Answer: Sp3

13. The hybridization of this carbon atom is - .

Answer: Sp3

14. The hybridization of this carbon atom is -.

Answer: Sp

15. The molecular formula C2H4O can be converted into three-line bond (Kekule) structures that are
consistent with valence rules. Which one of the following Kekule structures is not consistent with valence
rules?
H 0 H H 0 H H
I II \ / / \ \ I
a. H-C-C-H b. C=C c. H-C-C-H d. C-C=O
/ \ I I / I
I H O-H H H H H
H

Answer: d

16. Explain why the structure you chose in question 15 is not consistent with valence rules.

Answer: The carbon bonded to the oxygen atom in structure d is pentavalent; it has 10 valence electrons.
Carbon can only have eight valence electrons. In addition, the other carbon has only six valence
electrons when it would prefer to have eight.

Chapter 1: Structure and Bonding

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 17. Convert the following structure to a skeletal drawing and give its molecular fonnula

H Br
,/
H, C
/\/ 'C-H
H C-C II
\
H''''''\ ' H
H
3-bromo-l-cyclopentene

Answer:
Br

0
Molecular fonnula: CsH7Br

18. Draw an orbital picture for acetylene, CzHz. Clearly label each bond type and indicate the type of orbitals
involved in each bond.

Answer:

pi bonds

Propose possible structures for a molecule that meets each ofthe following descriptions:

19. Contains two Sp3 hybridized carbons and two sp hybridized carbons.

Answer:

H-C=C-CH2CH3
H3C-C=C-CH3

20. Contains one Sp3 hybridized carbon and two spz hybridized carbons.

Answer:
H3C- C== CH2
I
H

Test Items for McMurry's Organic Chemistry, Seventh Edition

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