Download Chapter 1 Answers

Chapter 1 Answers
1. What is the hybridization of each of the carbon atoms in the following compound?
2. What is the hybridization of each of the carbon, oxygen, and nitrogen atoms in the following
compounds?
sp2
sp3
O
N
N
H3C
3. Indicate the hybridization of the indicated atom:
CH3CH CH2
sp2
sp3
CH3CH2OH
sp
sp2
CH3CH NCH3
sp3
O
CH3CCH3
CH3C N
CH3OCH2CH3
4. Drew a Lewis structure for each of the following species:
a. H2CO3
b. CO32-,
c. CO2
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d. CH3NH2
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N
CH3
sp3
sp2
N
CH3
O
sp2
e. HCO3-
f. NH4Cl
or
g. NaOH
h. N2
or
I. CH3OCH3
J. C2H5OH
6. Show the direction of the dipole moment in each of the following bonds.
For example
CH3-Cl
7. Use the symbol δ+ and δ- to show the direction of polarity of the indicated bond in each of
the following compounds (example, δ− δ+
HO
H
)
δ+ δ−
δ+ δ−
δ- δ+
δ+ δ−
A. H3C-Cl
B. H3C-NH2
C. F-Br
D. H3C-OH
δ- δ+
F. H3C-MgBr
δ- δ+
E.
HO-Br
δ+ δ−
G.
I-Cl
δ+ δ−
H.
H2N-OH
8. Expand the following condensed structures to show the covalent bonds and non-bonding
pairs of electrons:
a. CH3NHCH2CH3
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B. (CH3)2CHCl
2
C. (CH3)2CHCHO
H
H
H
O
C
C
C
D. (CH3)3C(CH2)3CH(CH3)2
H
H
H
H
H
H
C
H
H
e. CH3CHO
H. CH3COOH
H
C
H
H
H
H
C
C
C
C
C
C
H
H
C
H
H
H
C
H
F.
H
H
H
(CH3)3COH
H
C
H
H
H
H
G. CH3OCH3
I. CH3CH(OH)CH2CN
H
H
O
H
H
C
C
C
H
H
H
C
N
9. Draw arrows to show the movement of electrons in the following reaction steps
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10. List the halide ions ( F-, Cl-, Br-, and I- ) in order from strongest base to weakest base.
The stronger the acid, the weaker (or more stable) base.
HI is the strongest acid, I- is the most stable (weakest) base.
HF is the weakest acid, F is the least stable (strongest) base.
F-, Cl-, Br- , and I11. Draw curved arrows to show where the electrons start from and where they end up in the following
reactions:
13. Which is a stronger based?
14.
15. (a) Draw the products of following acid-base reactions:
(b) Which of the following reactions favor the formation of the reactants and which favor the formation
of products?
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Chapter 2 Answers
1. a. 2,2,4-trimethylhexane b.
2,2-dimethylbutane c. 2,5-dimethylheptane d. 3,3-diethylhexane
e. 3,3-diethy-4-methyl-5-propyloctane f. 3-methyl-4-propylheptane
g. 5-ethyl-4,4-dimethyloctane
h. 4-isopropyloctane
2. a. 1-ethyl-2-methylcyclopentane b. ethylcyclobutane
d. 3,6-dimethyldecane
e.
2-cyclopropylpentane
c. 4-ethyl-1,2-dimethylcyclohexane
f. 1-ethyl-4-isobutylcyclohexane
g. 5-isopropylnonane
h. 1-sec-butyl-4-isopropylcyclohexane
3. Draw skeletal structures of the following compounds.
a. 5-ethyl-2-methyloctane
d. propyleycyclopentane
b. 1,3-dimethylcyclohexane e. 2-methyl-4-(1-methylethyl)octane
c. 2,3,3,4-tetramethylheptane f. 2,6-dimethyl-4-(2-methylpropyl)decane
a)
c)
b)
d)
e)
f)
4. Draw all the isomers that have molecular formula C5H11Br. (Hint: There are eight isomers.)
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5. Determine whether each of the following compounds is a cis isomer or a trans isomer.
a. cis
b. cis
c. cis
d. trans e. trans e. trans f. trans
6. Draw the two chair conformers of each compound and indicate which conformer is more stable.
a. cis-l-ethyl-3-methylcyclohexane
b. trans-l-ethyl-2-isopropylcyclohexane
c. trans-l-ethyl-2-methylcyclohexane
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d. trans-l-ethyl-3-methylcyclohexane
e. cis-l-ethyl-3-isopropylcyclohexane
f. cis-l-ethyl-4-isopropylcyclohexane
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7a. Draw the more stable chair conformer of cis-1-ethyl-2-methylcyclohexane.
b. Draw the more stable conformer of trans-1-ethyl-2-methylcyclohexane.
c. Which is more stable, cis-l-ethyl-2-methylcyclohexane or trans-1-ethyl-2-methylcyclohexane?
8. The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with
its five substituents all in equatorial positions.
Starting with the structure on the right, draw the most
stable form of glucose.
OH
O
HO
HO
OH
OH
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Chapter 3 Answers
1. Draw the structure of each of the following compounds.
a.
3,3-dimethylcyclopentene b. 6-bromo-2,3-dimethyl-2-hexene
c. ethyl vinyl ether
d.
CH3CH2OCH=CH2
allyl alcohol
CH2=CHCH2OH
2. Give the systemic name for each of the following compounds.
(a) 4-methyl-2-pentene
(b)
(c) 1-bromocyclopentene
(e) 1,5-dimethylcyclohexene (f) 1-butoxy-1-propene
(d) 1-bromo-4-methyl-3-hexene
3.
2-chloro-3,4-dimethyl-3-hexene
Tell whether the following compounds has the E or Z configuration.
(a) E
(b) Z (c) Z
(d) E
(e) Z
(f) Z (g) Z
(h) E
4. What would be the major product obtained from the addition of HBr to each of the following
compounds?
a.
c.
e,
CH3
CH3CCH2CH2CH2CH3
Br
b.
d.
f.
Br
CH3
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5 What alkene should be use to synthesize each of the following alkyl bromide?
6. Give the structure of the alcohol that formed from the acid-catalyzed hydration of each of the
following alkenes.
7.
How could the following compounds be prepared using an alkene as starting material?
A.
H+
CH3OH
+
OH
B.
+
C.
D.
+
H2O
CH3CH2OH
CH3
H2C
CH3
+
O
OH
H+
CH3
H+
O
CH3
CH3
O
CH3
H+
CH3OH
OH
E.
H2O
+
F.
+
H2O
H+
H+
OH
or
OH
+
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H2O
H+
+
OH
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8. Give the major product(s) obtained from the reaction of each of the following with HBr.
9. What will be the major product(s) of the following reactions?
The nucleophile that is present in higher concentration is more apt to collide with
the carbocation intermediate. Therefore, if the solvent is a nucleophile, the major
product from reaction of the solvent with the carbocation or cyclic bromonium (or
chloronium) intermediate, because the concentration of the solvent is much greater
than the concention the other nucleophile.
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10. Give the reagents that would be required to use for the following reactions.
11. How could you prepare the following compounds?
reagents.
You can use any alkene and any other
12. Give the major product(s) obtained from the reaction of each of the following with HBr.
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Chapter 4 Answers
1. Indicate whether each of the following pairs of compounds are identical or are enantiomers,
diastereomers, or constitutional isomers. Indicate the chiral centers and use R, S system
to identify them.
a. enantiomers
b. constitutional isomers
C. enantiomers
D. constitutional isomers
e. diastereomers
F. enantiomers
g. identical
H. enantiolners
constitutional isomers
identical
J. enantiomers
o. diastereomers
k. identical
L. diastereomers
p. constitutional isomers
2. Name each of the following stereocenters using R, S designation.
a. R
a. S
a. S
A. R, R
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b.
R
b. R
b. S
c.
R d. R
c. S
f. S
B. S,R
C. R,S
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M. identical
i.
n.
3. Give the products of the following reactions and their configuration:
H
H3C
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CH3
CH(CH3)2
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4. Draw perspective formulas for the following compounds:
a. (S)-3-chloro-1-pentanol
b. (2R,3R)-2,3-dibromopentane
c. (2S,3R)-3-methyl-2-pentanol
d. (R)-1,2-dibromobutane
(a)
(B)
H
Cl
H
Br
(C)
Br
H
H
(D)
OH
H
H
Br
Br
HO
5. Give the products of the following reactions.
stereoisomers are obtained.
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If the products can exist as stereoisomers, show which
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Chapter 5 Answers
1. Draw the structure for each of the following compounds.
g.
h.
i.
2. Give the major product of the following reactions:
3. Which alkyne would be the best reagent to use for the synthesis of each of the following ketones?
4. Which reagents could be used to the following reactions?
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5. What will be the major product of the reaction of 1 mole of propyne with each of the following
reagents?
.
6. Using ethyne as the starting material, how can the following compounds be prepared?
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7. Give the following stereomers obtained from the reaction of 2-butyne with the following reagents?
8. What reagents would you use for the syntheses?
a. (Z)-3-hexene from 3-hexyne b. (E)-3-hexene from 3-hexyne c. hexane from 3-hexyne
c. excess H2/Pt
a. H2/Lindlar’s catalyst b. Na, NH3
9. Show how each of the following compounds could be prepared using the given material, any
necessary inorganic reagents, and Any necessary organic compound that has no more than four atoms:
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10. What will be the major product of the following reactions?
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Chapter 6 Answers
(1) In each of the following pairs, which species is more stable?
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(2) Are the following pairs of structures resonance contributors or different compounds?
&
a. different
b. resonance
c. resonance
d.
resonance
(3) Draw resonance contributors of the following species:
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7.
8.
9.
(4) Which one of following pairs is more stable?
b.
c
(5) Draw the resonance contributors for the following
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Chapter 7 Answers
1. Give the systematic name for each of the following compounds:
a. 1,4-cycloheptadiene
b. 1-hepten-4-yne c. 1,6-dimethyl-1,3-cyclohexadiene
2. Give the major product of each following reactions (equivalent amounts of reagents are used in each
case):
c
e.
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g.
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M. 2,3-Dimethyl-1,3-pentadiene
+ HCl
N. 2,4-Dimethyl-1,3-pentadiene
+
HCl
3. Give the major product of the following reactions:
H2C
H2C
CH
CH
C
H
CH2
C
H
CH2
CH3C
+
HC
+
O
CH3 CH3
H2C
C
C
CH3
CH
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∆
C
C
C
O
C
CCH3
∆
N
O
CH2
CH3
+
H3CC
O
O
+
C
H
CCH3
O
O
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H2C
CH
C
H
CHC3
+
HC
C
C
N
+
HC
C
C
N
∆
CH3
H2C
H
C
C
CH2
∆
4. What diene and what dienophile should be used to synthesize the following compounds?
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