Federal University of Minas Gerais – Department of Chemistry

Organic Chemistry

Solved Exercises Solomons 7th ed.

1.1
a) d) g)

b) e) h)

c) f) i)

1.2
a) c) e)

b) d) f)

1.3
a) c) e)

b) d) f)

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

1.4
a)

b)ec)Since the two resonance structures are equivalent, each will have equal
contribution to the hybrid. The C-O bonds should therefore have equal distance and
each oxygen atom should have a negative charge of 0.5.

1.5
a) In its ground state, the valence electrons of carbon can be
arranged as shown in the figure below:
The orbitals are designated as 2px, 2py, and 2pz to indicate
its respective orientations along the x, y axes.
direction of unpaired electrons in the 2px and 2py orbitals
arbitrary. The formation of covalent bonds in methane from
of individual atoms requires the carbon atom
overlap your orbitals containing an electron with the 1s orbital
two hydrogen atoms (which also contain one electron). If
the carbon atom in the ground state is combined with
two hydrogen atoms, the result will be the formation of two
carbon-hydrogen bonds and they should be perpendicular to each other.
The formation of the hypothetical molecule CH2from the carbon atom in state
fundamental

b) An excited carbon atom can combine with four atoms of

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Federal University of Minas Gerais – Department of Chemistry
Organic Chemistry

The promotion of an electron from the 2s orbital to the 2pz orbital requires energy. This
energy spent can be obtained from the energy released when the two
additional covalent bonds are formed. There is no doubt that this is true, but
solve only one problem. The other problem that cannot be solved using the
excited state carbon atom as the basis for the model for methane are
problems of carbon-hydrogen bond angles and the apparent equivalence of
all four carbon-hydrogen bonds. Three of the hydrogens overlap their
orbitals with three p orbitals carbon, must in this model be at angles of 90º
one with another. The fourth hydrogen overlaps its 1s orbital with the 2s orbital of
carbon and must therefore have some other angle, probably the furthest from the
other connections. Basically, in this model of methane with carbon in a state
excited gives us a carbon that is tetravalent but it is not tetrahedral and produces a
structure for methane in which one carbon-hydrogen bond differs from the other three.

1.6
a) c)
H H H CH3
C C C C
H CH2CH3 H CH3
does not have cis-trans isomerism does not have cis-trans isomerism
b) d)
H3C H H H H H H Cl
C C C C C C C C
H CH3 H3C CH3 CH3 CH2 Cl CH3 CH2 H
trans cis Z E
does not have cis-trans isomerism,

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

1.7
The planar quadratic structure of the compound CH2Cl2has two isomers:

while its tetrahedral structure does not exhibit isomers

1.8
{"a":"There are four pairs of bonding electrons.","e":"There are three pairs of bonding electrons."}
around the central atom. The geometry is trigonal planar.
tetrahedral.

["b) There are two pairs of electrons around the","f) There are four bonding pairs of electrons to the"]
central atom. The geometry is linear around the central atom. The geometry is
tetrahedral.

c) There are four pairs of bonding electrons to g) There are four pairs of bonding electrons to
around the central atom. The geometry is around the central atom. The geometry is
tetrahedral. tetrahedral.

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Federal University of Minas Gerais – Department of Chemistry
Organic Chemistry

["d) There are two pairs of bonding electrons and not","h) There are three pairs of bonding electrons and one"]
Ligands. The geometry is angular. non-bonding around the central atom. And the
geometry is triangular pyramid.

1.9
a)

b)

c)

1.10

1.11
a)

b)

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Federal University of Minas Gerais – Department of Chemistry
Organic Chemistry

c)

d)

e)

f)

g)

h)

1.12
(a) and (d) are constitutional isomers with formula C5H12
(b) and (e) are constitutional isomers with formula C5H12O
(c) and (f) are constitutional isomers with formula C6H12

1.13
a)
H H H H H
H C C C C C C H
H Cl H H O H

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

b)
HO
H H H
C
H C C H
H C C H
H C H
H H
H C H
C C
H H H H

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

c)
H
H
H H
C
H C
C C C
C H
C C H
H H H
H H

1.15
a) No+ has electronic configuration: 1s22s22p6Do Ne.
b)Cl- has electronic configuration: 1s22s22p63s23p6of the architect.
c)F+ has electronic configuration: 1s22s22p5that does not correspond to that of a gas
noble.
d)H- has electronic configuration: 1s2do He.
e)Ca+2has electronic configuration: 1s22s22p63s23p6do Ar.
f)S2-has electronic configuration: 1s22s22p63s23p6do Ar.
g)O2- has electronic configuration: 1s22s22p63s23p6of Ar.
h)Br+ has electronic configuration: 1s22s22p63s23p63d104s24p4that does not match
a noble gas.

1.16
a) c)

b) d)

1.17
a) c)

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

b) d)

1.18
a)(CH3)2CHCH2OH c)
HC CH2
HC CH2
(CH3)2CHCOCH(CH3)2 d)(CH3)2CHCH2CH2OH

1.19
a)C4H10O c)C4H6
b)C7H14O d)C5H12O

1.20
a) Different non-isomeric compounds i) Different non-isomeric compounds
b) Constitutional isomers j) Even composed
c) Even composed k) Constitutional isomers
d) Even composed l) Different non-isomeric compounds
e) Even composed m) Even composed
f) Constitutional isomers n) Even composed
g)Different non-isomeric compounds o) Same compound
h) Same compound Constitutional isomers

1.21
a) d)
O

O OH
b) e)

c) f)
O
OH

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Federal University of Minas Gerais – Department of Chemistry
Organic Chemistry

1.22
a) c)
H H H H H
H H
H N C C H
H H
H H H
H H
N H H
H H
H H
b) d)
H H H
O
H H
H H
H H
H N H H H

1.23

1.24

1.26
H
C H
H
a) Formal charge 4 - (6/2 + 0) = +1
b) Load +
c)sp2

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

1.27
H
C H
H
a) Formal charge 4 - (6/2+2) = -1
b) Load -
c) Trigonal pyramid

d)sp3

1.28
H
C H
H
a) Formal charge 4 - (6/2 + 1) = 0
b) Without Load
c)sp2

1.29
a)eb)

c) Since the two resonance structures are equivalent, they have the same
contribution to hybridization and therefore the bonds must be of the same length.
Yes. We consider the central atom containing two groups and a pair of non-bonding electrons.
binders.

1.30

The AeC structures are equivalent and therefore have equal contributions to the
hybrid. The bonds of the hybrid, therefore, have the same length.

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Federal University of Minas Gerais - Department of Chemistry
Organic Chemistry

1.31
a)

b)

c)

d)

1.32
different compounds constitutional isomers
b) Constitutional isomers resonance structures
c) resonance structures f) even compound

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