Texas Woman University Chemistry Worksheet

Organic Chemistry, 9eby L. G. Wade, Jr.
Homework
Chapter 4
The Study of
Chemical Reactions
© 2017 Pearson Education, Inc.
© 2017 Pearson Education, Inc.
4.1 Identify the intermediate in the halogenation of
alkanes.
a)
b)
c)
d)
Anion
Cation
Radical
Dimer
© 2017 Pearson Education, Inc.
4.2 Describe the initiation step in the halogenation of
alkanes.
a)
b)
c)
d)
e)
Radicals are consumed.
Radicals are formed.
Radicals are consumed and formed.
Ions are formed.
Ions are consumed.
© 2017 Pearson Education, Inc.
4.3 Describe the propagation step in the halogenation
of alkanes.
a)
b)
c)
d)
e)
Radicals are consumed.
Radicals are formed.
Radicals are consumed and formed.
Ions are formed.
Ions are consumed.
© 2017 Pearson Education, Inc.
4.4 Describe the termination step in the halogenation
of alkanes.
a)
b)
c)
d)
e)
Radicals are consumed.
Radicals are formed.
Radicals are consumed and formed.
Ions are formed.
Ions are consumed.
© 2017 Pearson Education, Inc.
4.5 Identify the propagation step.
a)
b)
c)
d)
Cl2 → Cl• + Cl•
Cl• + CH3CH3 → CH3CH2• + HCl
Cl• + Cl• → Cl2
CH3CH2• + Cl• → CH3CH2Cl
© 2017 Pearson Education, Inc.
4.6 Identify the initiation step.
a)
b)
c)
d)
Cl2 → Cl• + Cl•
Cl• + CH3CH3 → CH3CH2• + HCl
Cl• + Cl• → Cl2
CH3CH2• + Cl• → CH3CH2Cl
© 2017 Pearson Education, Inc.
4.7 Identify the termination step.
a)
b)
c)
d)
Cl2 → Cl• + Cl•
Cl• + CH3CH3 → CH3CH2• + HCl
Cl• + Cl• → Cl2
CH3CH2• + Cl2 → CH3CH2Cl + Cl•
© 2017 Pearson Education, Inc.
4.8 A negative heat of reaction indicates which of the
following?
a)
b)
c)
d)
An exothermic reaction
An endothermic reaction
Neither exothermic nor endothermic reaction
Both exothermic and endothermic
© 2017 Pearson Education, Inc.
4.9 Where is the rate-limiting step in a reaction-energy
diagram?
a)
b)
c)
d)
The location of the starting material
The lowest point
The highest point
The location of the products
© 2017 Pearson Education, Inc.
4.10
a)
b)
c)
d)
Which halogen reacts the fastest with ethane?
F2
Cl2
Br2
I2
© 2017 Pearson Education, Inc.
4.11
Classify the underlined atom: (CH3)2CHCH2CH3.
a) Zero
b) Primary
c) Secondary
© 2017 Pearson Education, Inc.
d) Tertiary
e) Quaternary
4.12
Compare the first propagation step for chlorination
and bromination.
a) Endothermic for bromination, but exothermic for
chlorination
b) Exothermic for bromination, but endothermic for
chlorination
c) Exothermic for both bromination and chlorination
d) Endothermic for both bromination and chlorination
© 2017 Pearson Education, Inc.
4.13
a)
b)
c)
d)
Define a radical inhibitor.
A species that speeds up radical reactions
A species that slows down radical reactions
Has no effect on radical reactions
None of the above
© 2017 Pearson Education, Inc.
4.14
Identify the hybridization of a carbocation.
a) sp
b) sp2
c) sp3
d) sp4
© 2017 Pearson Education, Inc.
4.15
a)
b)
c)
d)
Which species is the most stable?
CH3+
CH3CH2+
(CH3)2CH+
(CH3)3C+
© 2017 Pearson Education, Inc.
4.16
Identify the hybridization of the free radical.
a) sp
b) sp2
c) sp3
d) sp4
© 2017 Pearson Education, Inc.
4.17
a)
b)
c)
d)
Which species reacts the fastest?
CH3•
CH3CH2•
(CH3)2CH•
(CH3)3C•
© 2017 Pearson Education, Inc.
4.18
a)
b)
c)
d)
Name CH2.
Carbocation
Radical
Carbanion
Carbene
© 2017 Pearson Education, Inc.
4.19
Identify the hybridization of a carbanion.
a) sp
b) sp2
c) sp3
d) sp4
© 2017 Pearson Education, Inc.
4.20
a)
b)
c)
d)
Which species is the most stable?
CH3:—
CH3CH2:—
(CH3)2CH:—
(CH3)3C:—
© 2017 Pearson Education, Inc.
Organic Chemistry, 9e
by L. G. Wade, Jr.
Homework
Chapter 5
Stereochemistry
© 2017 Pearson Education, Inc.
© 2017 Pearson Education, Inc.
5.1 Compare the physical properties of enantiomers.
a)
b)
c)
d)
Different physical properties
Same physical properties
Cannot determine
Same chemical properties
© 2017 Pearson Education, Inc.
5.2 Identify as R, S, or achiral.
a) R
b) S
c) Achiral
d) Cannot be determined
© 2017 Pearson Education, Inc.
5.3 Identify as R, S, or achiral.
a) R
b) S
c) Achiral
d) Cannot be determined
© 2017 Pearson Education, Inc.
5.4 Identify as R, S, or achiral.
a) R
b) S
c) Achiral
d) Cannot be determined
© 2017 Pearson Education, Inc.
5.5 Identify as R, S, or achiral.
a) R
b) S
c) Achiral
d) Cannot be determined
© 2017 Pearson Education, Inc.
5.6 Identify as R, S, or achiral.
a) R
b) S
c) Achiral
d) Cannot be determined
© 2017 Pearson Education, Inc.
5.7 Identify the type of isomer for (R)-2-pentanol.
a)
b)
c)
d)
Dextrorotatory isomer
Levorotatory isomer
Has to be experimentally determined
Neither
© 2017 Pearson Education, Inc.
5.8 Calculate specific rotation of 5.00 g/20.0 mL;
observed rotation of –40°; 5 dm cell.
a)
b)
c)
d)
–32°
32°
2°
–2°
© 2017 Pearson Education, Inc.
5.9 Explain an enantiomeric excess of 30% (–).
a)
b)
c)
d)
70% (+) and 30% (–)
70% (–) and 30% (+)
65% (+) and 35% (–)
65% (–) and 35% (+)
© 2017 Pearson Education, Inc.
5.10
a)
b)
c)
d)
Identify the type of alkene in CH3CH=C=CH2.
Isolated diene
Conjugated diene
Allene
Alkyne
© 2017 Pearson Education, Inc.
5.11
a)
b)
c)
d)
e)
Classify 2R,3S-2,3-dichloropentane and
2S,3S-2,3-dichloropentane.
Enantiomers
Diastereomers
Conformational isomers
Constitutional isomers
Identical
© 2017 Pearson Education, Inc.
5.12
a)
b)
c)
d)
e)
Classify 2S,3S-2,3-dichloropentane and
2R,3R-2,3-dichloropentane.
Enantiomers
Diastereomers
Conformational isomers
Constitutional isomers
Identical
© 2017 Pearson Education, Inc.
5.13
a)
b)
c)
d)
e)
Classify 2R,3S-2,3-dichlorobutane and
2S,3R-2,3-dichlorobutane.
Enantiomers
Diastereomers
Conformational isomers
Constitutional isomers
Identical
© 2017 Pearson Education, Inc.
5.14
a)
b)
c)
d)
e)
Classify 2R,3R-2,3-dichlorobutane and
2S,3S-2,3-dichlorobutane.
Enantiomers
Diastereomers
Conformational isomers
Constitutional isomers
Identical
© 2017 Pearson Education, Inc.
5.15
a)
b)
c)
d)
e)
Identify the number of stereoisomers for
3-bromo-2,4,5-trichlorohexane.
6 stereoisomers
8 stereoisomers
12 stereoisomers
16 stereoisomers
24 stereoisomers
© 2017 Pearson Education, Inc.
5.16
a)
b)
c)
d)
Define a meso compound.
A meso compound is an achiral molecule.
A meso compound has a plane of symmetry.
A meso compound has chiral carbons.
All of the above
© 2017 Pearson Education, Inc.
5.17
Identify a pair of diastereomers.
a) A and B
b) A and D
© 2017 Pearson Education, Inc.
c) B and C
d) None
5.18
Identify a pair of enantiomers.
a) A and B
b) B and D
© 2017 Pearson Education, Inc.
c) B and C
d) A and C
5.19
Identify a pair of meso compounds.
a) A
b) B
© 2017 Pearson Education, Inc.
c) C
d) A and D
5.20
a)
b)
c)
d)
Compare the properties of diastereomers.
Different physical properties
Same physical properties
Cannot determine
Same chemical properties
© 2017 Pearson Education, Inc.
Organic Chemistry, 9e
by L. G. Wade, Jr.
Homework
Chapter 6
Alkyl Halides:
Nucleophilic
Substitution
© 2017 Pearson Education, Inc.
© 2017 Pearson Education, Inc.
6.1 Give the IUPAC name for (CH3)2CBrCH2CH(CH3)2.
a)
b)
c)
d)
e)
2-Bromo-2,4-dimethylpentane
4-Bromo-2,4-dimethylpentane
2-Bromopentane
2-Bromoheptane
Isobutyl isopentyl bromide
© 2017 Pearson Education, Inc.
6.2 Give the IUPAC name for CH3CH(Cl)C(Br)2CH3.
a)
b)
c)
d)
e)
2-Chloro-3-bromobutane
2,2-Dibromopentane
3-Chloro-2-bromobutane
2,2-Dibromo-3-chlorobutane
2-Chloro-3,3-dibromobutane
© 2017 Pearson Education, Inc.
6.3 Name
a)
b)
c)
d)
.
Isobutyl bromide
Neopentyl bromide
tert-Butyl bromide
tert-Pentyl bromide
© 2017 Pearson Education, Inc.
6.4 Identify the vinyl chloride.
a)
b)
c)
d)
e)
ClCH2CH=CH2
ClCH=CH2
C6H5Cl
CH3CH2Cl
CH3CH(Cl)CH3
© 2017 Pearson Education, Inc.
6.5 Identify the secondary alkyl halide.
a)
b)
c)
d)
CH3Br
CH3CH2Br
CH3CH(Br)CH3
(CH3)3CBr
© 2017 Pearson Education, Inc.
6.6 Identify the type of intermolecular attraction
between alkyl halides.
a)
b)
c)
d)
Hydrogen bonding
London forces
Dipole–dipole
None
© 2017 Pearson Education, Inc.
6.7
a)
b)
c)
d)
CH2BrCH2CH=CH2
CH3CH(Br)CH=CH2
CH3CH2CBr=CH2
CH3CH2CH=CHBr
© 2017 Pearson Education, Inc.
6.8
a)
b)
c)
d)
e)
CH3CH2CHCl2
CH3CH(Cl)CHCl
CH3C(Cl)2CH3
CH3C(Cl)=CH2
CH3CH=CHCl
© 2017 Pearson Education, Inc.
6.9 Identify the strongest nucleophile.
a)
b)
c)
d)
CH3OH
(CH3)3COH
CH3O–
(CH3)3CO–
© 2017 Pearson Education, Inc.
6.10
a)
b)
c)
d)
Where does the nucleophile attack in an SN2
mechanism?
Back side
Front side
Both sides
Sideways
© 2017 Pearson Education, Inc.
6.11
a)
b)
c)
d)
Give the rate equation for an SN2 mechanism.
k[RX][RX]
k[RX][Nu]
k[Nu][Nu]
k[RX][B]
© 2017 Pearson Education, Inc.
6.12
a)
b)
c)
d)
Identify the alkyl halide that reacts the fastest in
an SN1 mechanism.
CH3Cl
CH3CH2Cl
(CH3)2CHCl
(CH3)3CCl
© 2017 Pearson Education, Inc.
6.13
a)
b)
c)
d)
Identify the best solvent for an SN1 reaction.
CH3OCH3
(CH3)3N
CH3CH2OH
CCl4
© 2017 Pearson Education, Inc.
6.14
a)
b)
c)
d)
In an SN1 reaction, a 2° carbocation is formed.
What happens next?
Rearrangement may occur to form a 1° carbocation.
Rearrangement may occur to form a 3° carbocation.
The nucleophile attacks.
The leaving group departs.
© 2017 Pearson Education, Inc.
6.15
a)
b)
c)
d)
e)
Give the IUPAC name for (CH3)2CHCH2Cl.
1-Chloro-2-methylpropane
1-Chloropropane
1-Chlorobutane
1-Chloro-3-methylpropane
2-Chlorobutane
© 2017 Pearson Education, Inc.