Problems 47

Drawing Organic Molecules (Section 1.7)

Shorthand methods are used to abbreviate the structure of organic molecules.

CH3 H CH3
= CH3 C C C CH3 = (CH3)2CHCH2C(CH3)3
H H CH3
skeletal structure I I I isooctane condensed structure
I I I
A carbon bonded to four atoms is tetrahedral. The best way to represent a tetrahedron is to draw two bonds in the plane, one bond
in front, and one bond behind.

Bond Length
Bond length decreases across a row and increases down a column of the periodic table (Section 1.6A).
Bond length decreases as the number of electrons between two nuclei increases (Section 1.10A).
Bond length decreases as the percent s-character increases (Section 1.10B).
Bond length and bond strength are inversely related. In general, shorter bonds are stronger bonds (Section 1.10).
Sigma () bonds are generally stronger than bonds (Section 1.9).

Electronegativity and Polarity (Sections 1.11, 1.12)

Electronegativity increases across a row and decreases down a column of the periodic table.
A polar bond results when two atoms of different electronegativity values are bonded together. Whenever C or H is bonded to N, O,
or any halogen, the bond is polar.
A polar molecule has either one polar bond, or two or more bond dipoles that reinforce.

PROBLEMS
Atomic Structure, Ionic Bonding, and Covalent Bonding
1.39 Two radioactive isotopes of iodine used for the diagnosis and treatment of thyroid disease have mass numbers of 123 and
131. For each isotope, give the following information: (a) the number of protons; (b) the number of neutrons; (c) the number of
electrons in the neutral atom; (d) the group number.
1.40 Label each bond in the following compounds as ionic or covalent.
a. NaI b. BrCl c. HCl d. CH3NH2 e. NaOCH3

Lewis Structures and Formal Charge

1.41 Assign formal charges to each carbon atom in the given species. All lone pairs have been drawn in.
H H
a. CH2 CH b. H C H c. H C H d. H C C
H H H
I I
1.42 Assign formal charges to each N and O atom in the given molecules. All lone pairs have been drawn in.
I I I
a. CH3 N CH3 c. CH3 N N e. CH3 O
OH
b. N N N : CH3 C CH3
d. f. CH3 N O

1.43 Draw one valid Lewis structure for each compound. Assume the atoms are arranged as drawn.
H O
a. CH2N2 H C N N c. CH3CNO H C C N O e. HCO3 H O C O
H H
H HCO2 O
CH CN
b. CH3NO2 H C N O d. H C O f. 2 H C C N
H O H

1.44 Draw a valid Lewis structure for each compound.

a. N2 b. (CH3OH2)+ c. (CH3CH2) d. HNNH e. H6BN

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 48 Chapter 1 Structure and Bonding

1.45 Draw an acceptable Lewis structure from each condensed structure, such that all atoms have zero formal charge.
a. diethyl ether, (CH3CH2)2O, the first general anesthetic used in medical procedures
b. acrylonitrile, CH2CHCN, starting material used to manufacture synthetic Orlon fibers
c. dihydroxyacetone, (HOCH2)2CO, an ingredient in sunless tanning products
d. acetic anhydride, (CH3CO)2O, a reagent used to synthesize aspirin

Isomers and Resonance Structures

1.46 Draw all possible isomers for each molecular formula.
a. C3H7Cl (two isomers) b. C2H4O (three isomers) c. C3H9N (four isomers)
1.47 Draw Lewis structures for the nine isomers having molecular formula C3H6O, with all atoms having a zero formal charge.
1.48 With reference to compound A drawn below, label each compound as an isomer, a resonance structure, or neither.

O O O O O
CH2
a. b. c. d.
+

1.49 With reference to species B, label each species as an isomer, a resonance structure, or neither.

+ + + +
a. b. c. d.
+
B

1.50 How are the molecules or ions in each pair related? Classify them as resonance structures, isomers, or neither.
CH3
a. CH3 O CH2CH3 and CH3 C OH c. and

H

b. and CH3 C C CH3 d. CH3CH2CH3 and CH3CH2CH2
H H

1.51 Add curved arrows to show how the first resonance structure can be converted into the second.

H H CH2 CH
+ 2
a. CH3 C
+
N CH3 CH3 C N CH3 c.

H H

O* > O * *
+
b. H C NH2 H C NH2

1.52 Follow the curved arrows to draw a second resonance structure for each species.
*
* +
O NH2
+ +
a. CH3 N N b. CH3 C CH CH2 c. + d.
CH3
c
1.53 Draw a second
-*
*
Cl>~>
resonance structure for each ion. *
*
KJ O
+
O OH
+
a. CH3 C O b. CH2 NH2 c. d. H C H

II
For each ion in Problem 1.53 draw the resonance hybrid.
1.54
1.55 Draw all reasonable resonance structures for each species. O
+

a. O3 c. N3 e. g.
+
O O

b. NO3 (a central N atom) d. CH3 C CH C CH3 f. CH2 CH CH CH CH2

II

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 Problems 49

1.56 Draw four additional resonance structures for the following cation. Then draw the resonance hybrid.
CH2

1.57 Rank the resonance structures in each group in order of increasing contribution to the resonance hybrid. Label the resonance
structure that contributes the most as 3 and the resonance structure that contributes the least as 1. Label the intermediate
contributor as 2.

O O O
+
a. CH3 C O CH3 CH3 C O CH3
+
CH3 C O CH3

CH3 CH3 CH3

<511 p. +
b. CH3 C N NH2 CH3 C N NH2 CH3 C N NH2
+

-P- the compounds and ions with curved arrows drawn below. When the curved arrows give a second valid resonance
1.58 Consider
u
structure, draw the resonance structure. When the curved arrows generate an invalid Lewis structure, explain why the structure
is unacceptable.

a. b. c. CH3CH2 C N d. O

pGeometry I? e
\y
1.59 Predict all bond angles in each compound.
Cl

a. CH3Cl b. NH2OH c. CH2 NCH3 d. HC CCH2OH e.

1.60 Predict the geometry around each indicated atom.

O
a. CH3CH2CH2CH3 c. e. CH3 C OH

b. (CH3)2N d. BF4 f. (CH3)3N

I
1.61 Draw the structure of halothane, CF3CHClBr, in three dimensions, using solid lines, wedges, and dashes to illustrate the position
1
of atoms. Halothane is a safe and widely used general anesthetic.

Drawing Organic Molecules

1.62 How many hydrogens are present around each carbon atom in the following molecules?
O OH
a. O b. N
N
OH COOH
H
HO
capsaicin fexofenadine
(spicy component of hot peppers) (nonsedating antihistamine)

1.63 Draw in all the carbon and hydrogen atoms in each molecule.
OH
OH
OH H
N
N
H
a. b. c. OH d. HO
menthol myrcene ethambutol estradiol
(isolated from (isolated from bayberry) (drug used to treat tuberculosis) (a female sex hormone)
peppermint oil)

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