Atkins_4e_Ch02_p57 4/24/07 2:14 PM Page 87

EXERCISES 87

2.37 Write the complete Lewis structure for each of the 2.49 Determine the formal charge on each atom in the
following compounds: (a) formaldehyde, HCHO, which as its following molecules. Identify the structure of lower energy in
aqueous solution “formalin” is used to preserve biological each pair.
specimens; (b) methanol, CH3OH, the toxic compound also $ $ $ $ $ $
$ © Cl ¬ O
(a) O $ ¬ Cl ¬ O
O

$
$
called wood alcohol; (c) glycine, H2C(NH2)COOH, the ƒ ˚ ˚ ˚
simplest of the amino acids, the building blocks of proteins. O H $
O H

$
$

$
$
2.38 Write the Lewis structure of each of the following organic $ $ $
compounds: (a) ethanol, CH3CH2OH, which is also called ethyl $ © C © $S
(b) O $ ¬C
O S

$
alcohol or grain alcohol; (b) methylamine, CH3NH2, a putrid-
smelling substance formed when flesh decays; (c) formic acid, $ $
(c) H ¬ C N H¬C ©N
$
HCOOH, a component of the venom injected by ants.
2.39 The following Lewis structure was drawn for a Period 3 2.50 Determine the formal charge on each atom in the
element. Identify the element. following ions. Identify the structure of lowest energy in each
case.
O $ $ $苶兩 2
$
$

(a) N © C © N苶兩
2
NΩC¬N

$
$ $ $ $ $
C
$l E C
$l
$

$ 兩 3 苶兩 3 苶兩 3
O 苶 O O

$
$

$
$

$
$
Cl
$
$

©
©
$ ˚ $ $ $ $ $
(b) O
$ ¬ As˚ ¬ O$ O
$ ¬ As
˚ ¬O O
$ © As © O$

$
$

©
2.40 The following Lewis structure was drawn for a Period 3 O O O

$
$

$
$

$
$
element. Identify the element. $ $
 $  $ 
O 苶兩 O 苶
兩
O 苶
兩

$
$

$
$

$
$
O
$
$

©
$ $ $ $ $ ˚ $ $ ˚ $
(c) O
$ © ˚I © O O
$ © I˚ © O O
$ ¬ I˚ ¬ O

$
C
$l E O $ $ $
$

$ O O O
$
$

$
$

$
$
Cl
$ $ $
$
$

2.41 Write the complete Lewis structure for each of the 2.51 Two contributions to the resonance structure are shown
following compounds: (a) ammonium chloride; (b) potassium below for each species. Determine the formal charge on each
phosphide; (c) sodium hypochlorite. atom and then, if possible, identify the Lewis structure of lower
energy for each species.
2.42 Write the complete Lewis structure for each of the
following compounds: (a) zinc cyanide; (b) potassium 苶兩  苶兩 
H
H
tetrafluoroborate; (c) barium peroxide (the peroxide ion is O22).
(a)
$ $ $ $
$ $ O S O
$

$
O S O
$

$ $
2.43 Anthracene has the formula C14H10. It is similar to
O O
$
$
$
$

benzene but has 3 six-membered rings that share common C∫C $

bonds, as shown below. Complete the structure by drawing in $ 苶兩 
$
O H O 苶兩 
H
$
$

$
$

multiple bonds to satisfy the octet rule at each carbon atom.

Resonance structures are possible. Draw as many as you can
$ $
(b) O S O O S O
$

$
$

$ $ $ $
find.
O O
$
$

$
$

$
H H H
˚ ˚ ˚ 2.52 Two Lewis structures are shown below for each species.
H¬ C C C H
C C C C¬ Determine the formal charge on each atom and then, if
appropriate, identify the Lewis structure of lower energy for
¬C C C C ¬ each species.
H C C C H
˚ ˚ ˚ $ $ $ $ $ $
(a) O S O O S O
$

H H H $ $ $ $
$
O O
$
$

$
$

2.44 Write the Lewis structures that contribute to the

resonance hybrid of the guanadinium ion, C(NH2)3. $ $ $ $
(b) O
$ $S O O
$ $S O
$

$ $
2.45 Draw the Lewis structures that contribute to the
2.53 Select from each of the following pairs of Lewis structures
resonance hybrid of nitryl chloride, ClNO2 (N is the central
the one that is likely to make the dominant contribution to a
atom).
resonance hybrid. Explain your selection.
2.46 Do H∫CΩN and H∫NΩC form a pair of resonance
$ $ $ 2 @ $
structures? Explain your answer. (a) $F ¬2Xe
$ @¬ $F $F ¬ Xe
$ © $F
$

$
$

2.47 Draw the Lewis structure and determine the formal charge $ $ $
(b) O
$ © C © O$ O
$ ¬C¬ ¬
¬O
$

on each atom in (a) NO; (b) N2; (c) CO; (d) C22; (e) CN.
2.48 Using only Lewis structures that obey the octet rule, draw 2.54 Select from each of the following pairs of Lewis structures
the Lewis structures and determine the formal charge on each the one that is likely to make the dominant contribution to a
atom in (a) CH3; (b) OCl; (c) BF4. resonance hybrid. Explain your selection.