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Chapter 18–1
Chapter 18 Amines and Neurotransmitters Solutions to In-Chapter Problems 18.1 To determine whether an amine is 1o, 2o, or 3o, count the number of carbons bonded to the nitrogen
atom as in Example 18.1. A 1o amine has one C–N bond, and so forth.
NC6H5
CCH3CH2O
O
CH3a. b.H2N(CH2)3NH(CH2)4NH(CH2)3NH2
1o 2o 2o 1o3o
18.2 Label the amine and hydroxyl group in scopolamine, a drug used to treat motion sickness, as 1o, 2o,
or 3o as in Example 18.1.
NCH3
O C CHO
CH2OH
O
scopolamine
3° amine1° hydroxyl group
18.3 Methamphetamine is a 2° amine. Give the molecular shape around each atom by counting groups.
CH2CHNHCH3
CH3
(1)3 groupstrigonal planar
(2)4 groups
tetrahedral
(3)3 atoms
1 lone pairtrigonal
pyramidal
a. 2° amine b.
18.4 Name each amine as in Example 18.2.
a. CH3CH2CHCH3
NH2butane butanamine(4 C's)
2 1
CH3CH2CHCH3
NH2
Answer: 2-butanamine
b. CH3CH2CH2 NHCH3
propane3 C's
propanamine
CH3CH2CH2 NHCH3
1
N-methyl
Answer: N-methyl-1-propanamine
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Amines and Neurotransmitters 18–2
N(CH3)2c.
6 C's in the ringcyclohexanamine
N(CH3)2
N,N-dimethyl
Answer: N,N-dimethylcyclohexanamine
d. (CH3CH2CH2CH2)2NH Answer: dibutylamine
2 butyl groups(4 C's)
18.5 Work backwards to draw the structure corresponding to each name.
d. N,N-diethylaniline
NHCH3
NH2
NH2
N
CH2CH3
CH2CH3
CH2CH3
CH3CH2
CH3CH2
a. N-methylaniline
b. m-ethylaniline
c. 3,5-diethylaniline
N-methyl
m-ethyl
1
3
5
3,5-diethyl
N,N-diethyl
18.6 Work backwards to draw the structure corresponding to each name.
h. N-propylaniline
CH3CH2CHCH2CH2CH3
NH2
CH3CH2CH2CH2CH2 NHCH3
O2N NH2
NCH3
CH3CH2NCH3
CH3
ONH2
NH2
CH2CH2CH3
HN
CH2CH2CH3
a. 3-hexanamine
b. N-methylpentylamine
c. p-nitroaniline
d. N-methylpiperidine
e. N,N-dimethylethylamine
!f. 2-aminocyclohexanone
g. 1-propylcyclohexanamine
3
N-methyl
p-nitro
N-methyl
N,N-dimethyl
12
2-amino
1
1-propyl
N-propyl
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Chapter 18–3
18.7 Determine the compound in each pair with a higher boiling point, using the rules in Example 18.3.
(CH3)2CHCH2NH2a. CH3C
CH2CH3
Oor
a ketone with only C–H bondsa 1o amine with N–H bonds
intermolecular hydrogen bondinghigher boiling point
b. (CH3)2CHCH2NH2 or (CH3)2CHCH2OH
a 1o amine with N–H bondsintermolecular hydrogen bonding
a 1o alcohol with an O–H bondintermolecular hydrogen bonding
stronger intermolecular forceshigher boiling point
NH2 CH3orc.
a 1o amine with N–H bondsintermolecular hydrogen bonding
higher boiling point
hydrocarbon
18.8 Caffeine is soluble in the organic solvent CH2Cl2 because caffeine is organic and “like dissolves like.”
18.9 Nicotine has two heterocycles: pyridine and pyrrolidine.
N N
CH3
pyridine pyrrolidine
18.10 Draw both enantiomers of nicotine.
N N
CH3
chirality center
NNCH3
H
N
H
NCH3
enantiomers 18.11 Morphine contains a 3° amine.
O
HO
NCH3HO
N is bonded to three groups: 3° amine.
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Amines and Neurotransmitters 18–4
18.12 Identify the functional groups in heroin.
O
O
NCH3O
CCH3
O
CCH3
O
ester
3o amine
alkene
aromatic ring
ether
ester 18.13 Quinine has 11 trigonal planar carbon atoms [part (a), labeled with *] and nine tetrahedral carbon
atoms [part (b), all other C’s].
N
CH2=CH
CH
N
CH3O
HO
quinine*
**
**
* **
*
**
18.14 Draw the products when the amines are treated with HCl as in Example 18.4.
(CH3CH3NH3) + Cl–+
(CH3CH2)2NH2++ Cl–
(CH3CH2)3NH+ + Cl–a.
b.
c.CH3CH2NH2
(CH3CH2)2NH
HCl
HCl
HCl(CH3CH2)3N
18.15 Draw the products of each reaction.
CH3CH2CH2CH2 NH2 HCl+a. (CH3CH2CH2CH2 NH3)+ + Cl–
C6H5COOH(CH3)2NH +b. C6H5COO–(CH3)2NH2 ++
NH
H2O+c.N
OH–+
+
HH
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Chapter 18–5
18.16 Draw the products of the reaction.
HO
HO CHCH2NHCH3OH
HO
HO CHCH2NH2CH3OH
+
HSO4–+
H2SO4
18.17 Name each ammonium salt as in Example 18.5.
a. (CH3NH3) Cl– b. [(CH3CH2CH2)2NH2] Br– c. [(CH3)2NHCH2CH3] CH3COO–
chloridederived from methylamine
methylammonium chloride
bromidederived from dipropylamine
dipropylammonium bromide
acetatederived from ethyldimethylamine
ethyldimethylammonium acetate 18.18 Ammonium salts are water-soluble solids. A water-insoluble amine can be converted to a water-
soluble ammonium salt by treatment with acid.
a. Cl–Br–(CH3CH2)3N b. [(CH3CH2)3NH] c. CH3CH2NH2 d. NH
H3° amine with 6 C's
water insolubleammonium saltwater soluble
1° amine with 2 C'swater soluble
ammonium saltwater soluble
18.19 Draw the products of each reaction.
a. Cl–Br– c.
b.
[(CH3CH2)3NH] NH
H
(CH3CH2NH3) HSO4–
(CH3CH2)3N NH
CH3CH2NH2
NaOH
NaOH
NaOH+ H2O + NaBr
+ H2O + NaHSO4+ H2O + NaCl
18.20 Draw the structure of each amine from which the ammonium salt is derived.
CHCH2 N CH3H
OHC
CCH2CH3CH2
O
CHCH3
N CH3CH3
HO
methadonephenylephrine
18.21 A quaternary ammonium salt like Bitrex has four R groups bonded to N, so there is no proton
available that can be removed to form an amine.
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Amines and Neurotransmitters 18–6
18.22 The chirality center in each compound is labeled.
CHCH2NH2HO
HOOH
norepinephrine
CH2CHNH2HO
HO
dopamine
CH2CHNH2HOCOOH
tyrosine
CH2CHNH2HOCOOH
HO
L-dopa
H
* = chirality center
*
*
*
achiral
18.23 COOH must be removed and OH must be added.
NH
HOCH2CH2NH2
serotonin
NH
CH2CHNH2
tryptophan
COOH
The COOH group is removed, and the OH group is added.
18.24 Serotonin, bufotenin, and psilocin have the same ring system with a two-carbon chain containing a
N atom bonded to it. They all contain an OH group bonded to the six-membered ring.
NH
HOCH2CH2N(CH3)2
NH
CH2CH2N(CH3)2OH
NH
HOCH2CH2NH2
2o 2o 2o
3o3o1o
serotonin bufotenin psilocin 18.25 To convert phenylephrine to methamphetamine requires the addition of a methyl group and
removal of two OH groups. 18.26 The atoms of 2-phenylethylamine are in bold in each compound.
CH3O
CH3O CH2CH2NH2
CH3O mescaline
a.
N
N
H
C CH3O
(CH3CH2)2N
LSD
b.
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Chapter 18–7
18.27 Classify each alcohol and amine as 1°, 2°, or 3°. OH groups not labeled are phenols.
HO
HOCH2
CHCH2NHC(CH3)3
albuterol(Trade names: Ventolin, Proventil)
HO
HOCH2
CHCH2NH(CH2)6O(CH2)4
salmeterol(Trade name: Serevent)
OH OH
2° alcohol 2° alcohol
1° alcohol 1° alcohol2° amine 2° amine
18.28 Draw the complete structure for cimetidine.
CC
NCN
H CH
HH
CH
HS C
H
HCH
HNH
CNC N
NH
CH
HH
H
Solutions to End-of-Chapter Problems 18.29 To determine whether an amine or amide is 1o, 2o, or 3o, count the number of carbons bonded to
the nitrogen atom as in Example 18.1.
3° amine2° amide 18.30 To determine whether an amine or amide is 1o, 2o, or 3o, count the number of carbons bonded to
the nitrogen atom as in Example 18.1.
NN
OCH3
3° amine
3° amide
18.31 To determine whether an amine is 1o, 2o, or 3o, count the number of carbons bonded to the nitrogen atom as in Example 18.1.
CH3CHCH2CH2NHCH3CH3
N CH3a. b.
2o 3o
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Amines and Neurotransmitters 18–8
18.32 To determine whether an amine is 1o, 2o, or 3o, count the number of carbons bonded to the nitrogen atom as in Example 18.1.
CH3CCH2NH2CH3
a. b.
1oCH3
N(CH3)2
3o
18.33 Draw a structure to fit each description.
CH3CH2CH2CH2CH2NH2 CH3CH2CH2NCH2CH2CH3
HCH3CH2NCH2CH3
CH2CH3
CH2CH3+
a. b. c. d.N CH3
1° amineC5H13N
2° amineC6H15N
3° amineC6H13N
quaternary ammonium ion
C8H20N+
18.34 Draw a structure to fit each description.
HOCH2CH2CH2CH2NH2a.
1o alcohol 1o amine
b. CH3CHCH2NHCH3
OH
2o alcohol
2o amine
c. HOCCH2NH2
CH3
CH3
1o amine
3o alcohol
d. NCH3 CH2CH2OHCH3
3o amine
1o alcohol 18.35 Name each amine as in Example 18.2.
a. b.
N-ethyl-N-methylaniline
cyclohexane
cyclohexanamine
ethyl
methyl
aniline
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Chapter 18–9
18.36 Name each amine as in Example 18.2.
a.
b.
2 methyl groups
N,N-dimethylpentanamine
Cl NH2
m-chloro
m-chloroaniline
CH2CH2CH2CH2CH2 NCH3
CH3
18.37 Name each amine as in Example 18.2.
CH3CH2 NH
CH2CH3a.
2 ethyl groups
Answer: diethylamine
CH3CH2CHCH2CH2CH2CH2CH3
NH2
b.1octane
(8 C's)octanamine
CH3CH2CHCH2CH2CH2CH2CH3
NH2
2 3
Answer: 3-octanamine
CH3CH2CH2CHCH2CH3
NHCH3c.
hexane(6 C's)
hexanamine
CH3CH2CH2CHCH2CH3
NHCH3
123
N-methylAnswer: N-methyl-3-hexanamine
CH3CHCH2CH2CH2CH2CH3
NHCH2CH3
d. Answer: N-ethyl-2-heptanamine
heptane(7 C's)
heptanamine
CH3CHCH2CH2CH2CH2CH3
NHCH2CH3 N-ethyl
21
18.38 Name each amine as in Example 18.2.
CH3(CH2)6NH2a. Answer: 1-heptanamineheptane heptanamine(7 C's)
b. Answer: N-ethylcyclopentanamineNHCH2CH3
cyclopentane(5 C ring) N-ethyl
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Amines and Neurotransmitters 18–10
c. Answer: N-ethylpyrrolidineN
pyrrolidine N-ethyl
CH2CH3
d. Answer: N-ethyl-N-methyl-2-propanamineCH3CHCH3
N CH2CH3
CH3
propane(3 C's)
propanamine
CH3CHCH3
N CH2CH3
CH3
1 2 3
N-methylN-ethyl
18.39 Work backwards to draw the structure corresponding to each name.
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2NH2
N
NH2
Br
CH3CHCH2COOH
CH3CH2CH2CH2CH2CH2CHCH3
N(CH2CH2CH3)2
CH3CH2NHCH2CH2CH2CH2CH2CH3
NH2
f. N-ethylhexylamine
a. 1-decanamine
b. tricyclohexylamine
c. p-bromoaniline
d. 3-aminobutanoic acid
e. N,N-dipropyl-2-octanamine
p-bromo
3-amino
13
N,N-dipropyl
N-ethyl
3 cyclohexyl groups
18.40 Work backwards to draw the structure corresponding to each name.
NHCH2CH2CH2CH2CH3
CH3CHCCH3
CH3CHCH2CH2NH2
NH2
f. N-ethyl-N-propylcyclopentylamine
a. cyclobutylamine
b. 4-nonanamine
c. N-pentylaniline
d. 3-amino-2-butanone
e. 3-methyl-1-butanamine
3-amino 1
3
N-ethyl
NH2
CH3CH2CH2CHCH2CH2CH2CH2CH3
NH2
4
N-pentyl
O
CH3
13
N CH2CH2CH3
CH2CH3 N-propyl
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Chapter 18–11
18.41 Draw the structures to illustrate the differences between N,N-dimethylaniline and 2,4-diethylaninline
N(CH3)2 NH2
CH2CH3CH3CH2
N,N-dimethylaniline 2,4-diethylaniline
3° amine 1° amine
18.42 Draw the structures to illustrate the differences between N-butylaniline and o-butylaniline.
NH(CH2)3CH3 NH2
CH2CH2CH2CH3
N-butylaniline o-butylaniline
2° amine 1° amine
18.43 Work backwards from the name to draw each ammonium salt.
c. ethyldimethylammonium hydroxide
[(CH3CH2CH2)2NH2]+ ++
Cl– (CH3CH2CH2CH2NH3) Br– CH3CH2N(CH3)2 OH–
H
a. dipropylammonium chloride b. butylammonium bromide
ethyl
dimethyl 18.44 Work backwards from the name to draw each ammonium salt.
c. ethylmethylammonium chloride
+CH3CH2NCH3
–ClH
a. cyclohexylammonium fluoride b. triethylammonium iodide
ethyl
methyl
NH3+
F– NHCH2CH3
CH3CH2
CH2CH3
+ I–
H
18.45 Draw and name the four amines of molecular formula C3H9N.
NCH3
CH3 CH3 CH3CH2CH2NH2 CH3CH2NHCH3
trimethylamine 1-propanamine N-methylethanamine
CH3CHNH2CH3
2-propanamine
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Amines and Neurotransmitters 18–12
18.46 Draw and name the eight constitutional isomers of molecular formula C4H11N. Identify the chirality center present in one of the amines.
CH3CH2CHCH3
NH2
CH3CH2CH2CH2NH2*
chirality center
1-butanamine 2-aminobutane
CH3CHCH2NH2
CH3
2-methyl-1-propanamine
CH3CCH3
CH3
NH2
2-amino-2-methylpropane
CH3CH2CH2NHCH3
N-methyl-1-propanamine
CH3CH2NHCH2CH3
diethylamine
CH3CHNHCH3
CH3
N-methyl-2-propanamine
CH3CH2NCH3
CH3
N,N-dimethylethanamine 18.47 Pyridine is capable of hydrogen bonding with water, so it is more water soluble than benzene.
Pyridine has a higher boiling point than benzene because it contains polar C–N bonds, while benzene is a nonpolar hydrocarbon.
18.48 CH3CH2CH2NH2 is water soluble because it is capable of hydrogen bonding with water.
CH3CH2CH2CH3 is not water soluble because it is a nonpolar hydrocarbon and cannot hydrogen bond to water.
18.49 Determine the compound in each pair with a higher boiling point, using the rules in Example
18.3.
a.
b.
c.CH3CH2CH2NH2 or CH3(CH2)7NH2
CH3(CH2)6OH or CH3(CH2)6NH2
CH2N(CH3)2 CH2CH2CH2NH2or
alcoholhigher
boiling point
amine
3 C amine 8 C aminehigher
boiling point 3° amineno N–H bonds
1° amineN–H bonds
higherboiling point
18.50 Determine the compound in each pair with the higher boiling point using the rules in Example
18.3.
a.
b.
c.
ketone aminehigher
boiling point
1° amine
(CH3CH2)2C O or (CH3CH2)2CHNH2
NHor
hydrocarbon aminehigher
boiling point
CH3CHCH2CHCH3
Cl NH2
or CH3CH2CH2CHCH3
NH3+
Cl–
ammonium salthigher
boiling point
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Chapter 18–13
18.51 The hydrogen bond is drawn as a dashed line.
NCH2CH3
HCH2CH3
NCH3CH2
CH3CH2H
18.52 The hydrogen bond is drawn as a dashed line.
NCH3CH2
CH3CH2H
OH
H
18.53 Primary amines can hydrogen bond to each other, whereas 3o amines cannot. Therefore, 1o
amines have higher boiling points than 3o amines of similar size. Since all amines contain nitrogen atoms, any amine can hydrogen bond to water. Therefore, 1o and 3o amines have similar solubility properties.
18.54 CH3(CH2)5NH3
+Cl is more water soluble than CH3(CH2)5NH2 because the ammonium salt is an ionic solid and therefore soluble in water. CH3(CH2)5NH2 contains six carbons and is therefore not water soluble.
18.55 Draw the reaction of each amine with water by transferring a proton from H2O to the amine.
a. CH3CH2NH2 + H2O (CH3CH2NH3)+
+ OH–
+
b. (CH3CH2)2NH + H2O (CH3CH2)2NH2 + OH–
+
c. (CH3CH2)3N + H2O (CH3CH2)3NH + OH–
18.56 Draw the ammonium salt that is formed when each amine is treated with HCl.
+NH2 + HCla. NH3 Cl –
+CH2NHCH3 + HClb. CH2NH2CH3 Cl –
+N(CH2CH3)2 + HClc. NH(CH2CH3)2 Cl –
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Amines and Neurotransmitters 18–14
18.57 Draw the products of each reaction.
a. CH3CH2CH2N(CH3)2 + HCl CH3CH2CH2NH(CH3)2 + Cl–+
b. CH3CH2CHCH2CH3
NH2+ H2SO4 CH3CH2CHCH2CH3
NH3+ HSO4
–
+
c.N
+ HBrNH
+ Br–+
CH3CH2 NH
CH2CH3
CH2CH3
++d. NaOH CH3CH2 N CH2CH3
CH2CH3
+ H2O + Na+
18.58 Draw the products of each acid–base reaction.
a. + HCl + Cl–+N N
H
b. + H2SO4 + HSO4–
+
CH3CH2CHCH2CH3NHCH3
CH3CH2CHCH2CH3NH2CH3
c. + CH3COOH + CH3COO–+
CH3NH2 CH3NH3
CH3(CH2)5NH3+
+d. NaOH CH3(CH2)5NH2 + H2O + Na+
18.59 Draw the products of each reaction.
a.NH
CH2CH2CH3 N CH2CH2CH3
+
Cl–
H H
HCl
O
HO
NCH3HO
b. O
HO
NCH3HO
+
Cl–H
HCl
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Chapter 18–15
18.60 Draw the products of each reaction.
+CH2CHNH2
CH3
a. + H2SO4 CH2CHNH3CH3
HSO4–
+
CH2CH2NH2b. + H2SO4 HSO4–HO
HO
CH2CH2NH3HO
HO
18.61 The heterocycle in both coniine and morphine is piperidine (labeled in bold).
O
HO
NCH3HO
morphine
NH
CH2CH2CH3
coniine
18.62 The pyrrolidine N is trigonal pyramidal because it is surrounded by four groups, three of which
are bonds and one of which is a lone pair of electrons. The pyridine N has only three groups around it, two of which are bonds and one of which is a lone pair. The pyridine N doesn’t have enough groups around it to be trigonal pyramidal.
N NCH3
trigonal pyramidaltrigonal planar 18.63 Caffeine is a mild stimulant, imparting a feeling of alertness after consumption. It also increases
heart rate, dilates airways, and stimulates the secretion of stomach acid. These effects are observed because caffeine increases glucose production, making an individual feel energetic.
18.64 Caffeine intake should be limited in pregnant and nursing mothers because excessive
consumption increases the risk of miscarriage and caffeine can pass into breast milk, possibly affecting the health of a newborn baby.
18.65 An alkaloid solution is slightly basic since its amine pulls off a proton from water, forming OH–
and an ammonium ion. 18.66 a. Morphine is found in poppies and is used as a pain reliever for people suffering from severe
chronic pain. b. Quinine is found in the bark of the cinchona tree and is used to treat malaria. c. Atropine is found in the nightshade plant and is used to increase heart rate.
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Amines and Neurotransmitters 18–16
18.67 Dopamine affects brain processes that control movement, emotions, and pleasure. Normal dopamine levels give an individual a pleasurable, satisfied feeling. Increased levels result in an intense “high.” Drugs such as heroin, cocaine, and alcohol increase dopamine levels. When there is too little dopamine in the brain, an individual loses control of fine motor skills and Parkinson’s disease results.
18.68 Patients with Parkinson’s disease cannot be treated by giving them dopamine, even though the
disease results from low dopamine levels, because dopamine does not cross the blood–brain barrier.
18.69 Serotonin plays an important role in mood, sleep, perception, and temperature regulation. We get
sleepy after eating a turkey dinner on Thanksgiving because the unusually high level of tryptophan in turkey is converted to serotonin. A deficiency of serotonin causes depression.
18.70 Two examples of SSRIs are fluoxetine (Prozac) and sertraline (Zoloft). They combat depression
by inhibiting the reuptake of serotonin by the presynaptic neuron. 18.71 Dopamine [part (a)] and norepinephrine [part (b)] are derived from tyrosine, serotonin [part (c)] is
derived from tryptophan, and histamine [part (d)] is derived from histidine. 18.72 A neurotransmitter is a chemical messenger that transmits nerve impulses from one nerve cell
(neuron) to another cell. A hormone is a compound produced by an endocrine gland, which then travels through the bloodstream to a target tissue or organ.
18.73 The atoms of 2-phenylethylamine are labeled in bold in the compounds below.
CH2CH2CH2NH2a. b. c.C
CH3
CH3
CH2N(CH3)2 CH2HN
not a derivative of2-phenylethylamine
18.74 The atoms of 2-phenylethylamine are labeled in bold in the compounds below.
a. b. c.CCH3
CH3
C CH2CH2
not a derivative of2-phenylethylamine
CH3
NHCH3
CH3 CH2NH N
18.75 The atoms of 2-phenylethylamine are labeled in bold.
CH2CNH2
CH3
CH3
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Chapter 18–17
18.76 The atoms of 2-phenylethylamine are labeled in bold.
CHCH2NHC(CH3)3HO
HOCH2
OH
18.77 Chlorpheniramine is an example of an antihistamine. Antihistamines bind to the H1 histamine
receptor, but they evoke a different response than histamine. An antihistamine like chlorpheniramine or diphenhydramine, for example, inhibits vasodilation, so it is used to treat the symptoms of the common cold and environmental allergies.
18.78 Cimetidine is an anti-ulcer drug. It binds to the H2 histamine, thus reducing acid secretions in the
stomach. 18.79 Answer each question about benzphetamine.
CH2CHNCH2
CH3
CH3
chirality center
3o aminea. and b.
CC NCH2
CH3
H CH3
CCH2N C
CH3
HCH3
H
H
H
H
c.
enantiomers
CH2CHNH2
CH3
CH3
CH2
d.1° amine
constitutional isomer
CH2CH2N
CH2
e.CH3
CH3
3° amineconstitutional isomer
f. CH2CHNHCH2
CH3
CH3
+
Cl– benzphetamine hydrochloride
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Amines and Neurotransmitters 18–18
CH2CHNCH2CH3
CH3
+ CH3COOH CH2CHNHCH2CH3
CH3
++
g. CH3COO–
18.80 Answer each question about phentermine.
1o amineCH2CNH2
CH3
CH3
a.
CH2CNH2
CH3
CH3
tetrahedral
tetrahedral
trigonal pyramidal
trigonal planar
b.
CH2CHCH2NH2
CH3
c.
CH2CHNHCH3
CH3
d.
CH2CNH3
CH3
CH3
e. Br–+
CH2CNH2
CH3
CH3
f. CO
HO+ CH2CNH3CH3
CH3
–OCO
++
18.81 Answer the questions about Ritalin.
CH
COOCH3
HN
2o amine
ester
aromatic ring
a., b., and c.
chirality center
CH
COOCH3
N+
Cl–e.
d. 2-phenylethylamine in bold
HH
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Chapter 18–19
18.82 Answer the questions about seldane.
(CH3)3C CHCH2CH2CH2
OHN C
OH
2° alcohol
aromatic ring
aromatic ring
3° amine 3° alcohol
a., b., c., d., and e.
quaternary carbonchirality center
(CH3)3C CHCH2CH2CH2OH
N COH
f.+
Cl–
18.83 Work backwards to draw the structure of the amine and carboxylic acid that are used to form Chlortrimeton, an ammonium salt.
CHCH2CH2N(CH3)2
N
ClH
C CH
HOOC COO–
H
+
chlorpheniramine maleateChlortrimeton
CHCH2CH2N(CH3)2
N
ClC C
H
HOOC COOH
H
18.84 Draw the structure of the dextromethorphan hydrobromide.
CH3O
NHCH3
+ Br–
18.85 A vasodilator dilates blood vessels and a bronchodilator dilates airways in the lungs. Histamine is
a vasodilator and albuterol is a bronchodilator. 18.86 Antihistamines that cause drowsiness are able to cross the blood–brain barrier and bind to H1
receptors in the central nervous system. Antihistamines that do not cause drowsiness also bind to H1 receptors, but they are unable to cross the blood–brain barrier and bind to the H1 receptors in the central nervous system.
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Amines and Neurotransmitters 18–20
18.87 Albuterol will exist in the ionic form in the stomach (lower pH) and in the neutral form in the intestines.
HO
HOCH2
CHCH2NHC(CH3)3
OHHO
HOCH2
CHCH2NH2CH(CH3)3
OH +
ionic form neutral form
albuterol 18.88 Eating a poppy seed bagel can produce a positive test in a drug screening because poppy seeds
contain morphine. 18.89 Heroin has two esters, which can be made from the two OH groups in morphine. Add acetic acid
(CH3COOH) and H2SO4 to make the two esters in heroin.
O
HO
NCH3HO
O
O
NCH3O
CCH3
O
morphine heroin
CCH3
O
Both OH groups are converted to esters.
CH3COOHH2SO4
18.90 The compound that might cause the odor that allows for heroin detection is acetic acid, the main
ingredient in vinegar.
O
O
NCH3O
CCH3
O
heroin
CCH3
O+ 2 H2O C
O
CH3 OHO
HO
NCH3HO
+
acetic acid(vinegar)
2
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