Solution Manual For Experimental Organic Chemistry A Miniscale and Microscale Approach 6th Edition by Gilbert Martin

Section 2.
Chemicals and Special Equipment by Chapters Experimental Organic Chemistry: A Miniscale and Microscale Approach
Solution Manual for Experimental Organic Chemistry

A Miniscale and Microscale Approach 6th Edition by
Gilbert Martin
ISBN 1305080467 9781305080461
Full link download

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a-miniscale-and-microscale-approach-6th-edition-by-gilbert-martin-isbn-
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SECTION 2. CHEMICALS AND SPECIAL EQUIPMENT BY CHAPTERS

The amount provided is that required for 10 students. The equipment listed in this section is that needed in addition to
the standard equipment listed in Section 1.
CH 3 Solids: Recrystallization and Melting Points. 3.2
Recrystallization
Chemicals: Quantity
Miniscale Microscale
Acetanilide 0.60 g
Benzoic acid 0.60 g
Naphthalene 0.60 g
Resorcinol 0.60 g
Petroleum ether (bp 60–80 °C) 30 mL
Impure benzoic acid 10 g 1.0 g

Impure acetanilide 10 g 1.0 g
Impure naphthalene 10 g 1.0 g
Decolorizing carbon 1–2 g 0.5 g
Filter aid (Celite) 10 g 2.0 g

Methanol, 95% ethanol, or 2-propanol 250 mL 30 mL
6
2016 Cengage Learning. All rights Reserved. May not be scanned, copied, or duplicated, or posted to a publicly accessible website, in whole or
in part.
Section 2. Chemicals and Special Equipment by Chapters Experimental Organic Chemistry: A Miniscale and Microscale Approach
Other solvents, e.g., those listed in Table 3.1, may be needed if an unknown compound has been
assigned for recrystallization. About 500 mL of each such solvent is required per 10 students.
3.3 Physical Constants: Melting Points.
Parts A/B. Melting Points.
Chemicals (Standards for calibration): Quantity
7
in part.
3-Phenylpropanoic acid 0.2 g

Acetamide 0.2 g
Acetanilide 0.2 g
Benzamide 0.2 g
Salicylic acid 0.2 g
4-Chloroacetanilide 0.2 g
3,5-Dinitrobenzoic acid 0.2 g

Equipment: Quantity
Thiele tubes 10
or electric melting point apparatus 1
Packing tubes 10
Parts A/B. Melting Points. (cont.)
Equipment: Quantity
Capillary tubes 100
Compounds for Melting Point Unknowns
Compound Melting point (°C)
1,3-Dinitrobenzene 90
Acetanilide 114
Benzoic acid 122 Benzamide 130
Phthalic anhydride 131
Urea 132
trans-Cinnamic acid 133
p-Acetophenetidide (phenacetin) 135
o-Chlorobenzoic acid 142
Salicylamide 142 Benzilic acid 150
Adipic acid 153 Salicylic acid 158
Benzanilide 163
p-Bromoacetanilide 167
p-Toluic acid 178 Succinic acid 188
3,5-Dinitrobenzoic acid 207
Part C. Who Else Has My Compound?
Suggested compounds for unknowns. All compounds should be colorless, and samples should be
numbered in such a way that they cannot easily be decoded. Samples should be dispensed such that there
8
in part.
are two or three students per compound in the lab.

Quantity/3 students
Acetanilide 0.6 g
Ethyl p-Hydroxybenzoate 0.6 g
Urea 0.6 g
(E)-Cinnamic acid 0.6 g
Phenacetin 0.6 g
Aspirin (sodium acetylsalicylate 0.6 g
p-Phenylphenol 0.6 g
Part C. Who Else Has My Compound? (cont.)
Quantity/3 students
4-Hydroxyacetanilide 0.6 g
p-Toluic Acid 0.6 g
p-Anisic Acid 0.6 g
Equipment: Quantity
Thiele tubes 10
or electric melting point apparatus 1
Packing tubes 10
Melting-point capillaries 50
TLC chambers 10
250 µm pre-coated silica gel TLC plates with fluorescence indicator
cut into ~ 3-cm x 10-cm strips 60 strips
Capillary pipets 20
Compounds for Melting Point Unknowns
Compound Melting point (°C)
Acetanilide 113–115
Ethyl p-hydroxybenzoate 114–117
Urea 132–135
trans-Cinnamic acid 132–135
Phenacetin 133–136 (dec.)
Aspirin 134–136
p-Phenyphenol 164–166
4-Hydroxyacetanilide 168–172
p-Toluic acid 177–180
p-Anisic acid 182–185
9
in part.
CH 4 Liquids: Distillation and Boiling Points

4.2 Boiling Points of Pure Liquids
Chemicals:
Suggestions for possible boiling point unknowns are provided below.
Equipment: Quantity
Thiele tubes 10
Capillary tubes for micro boiling points 20
6- to 8-mm Tubing for samples 10
4.2 Boiling Points of Pure Liquids (cont.)
Compounds for Boiling Point Knowns and Unknowns

Compound Boiling point (°C)
Ethanol 78
1-Chlorobutane 78
2-Butanone (methyl ethyl ketone) 80
Cyclohexane 81 2-Propanol 83
2-Methyl-2-propanol (tert-butyl alcohol) 83
Methyl isobutyrate 93
Heptane 98 2-Butanol 100
2-Methyl-2-butanol 102
2-Methyl-1-propanol 108
Toluene 111
1-Butanol 118
Acetic acid 118
Tetrachloroethylene 131
Chlorobenzene 132
4-Methyl-2-pentanol 132
Ethylbenzene 136 Isopropylbenzene 152 Cyclohexanone
156 Bromobenzene 156
Anisole 156
Cyclohexanol 161
tert-Butylbenzene 168 sec-Butylbenzene 172 Isobutylbenzene
172 1,3-Dichlorobenzene 179 Ethyl acetoacetate 181
n-Butylbenzene 183
1
0
in part.
10
in part.
4.3 and 4.4 Simple and Fractional Distillation

Chemicals: Quantity
Simple distillation:
Cyclohexane with non-volatile dye 100 mL 20 mL
Fractional distillation:
Cyclohexane 100 mL
Toluene 200 mL
Equipment:
Copper or stainless steel gauze, Raschig rings or other column
packings
Aluminum foil and/or glass wool (optional) for
insulating columns
4.6 Steam Distillation of Citral from Lemon Grass Oil
Chemicals: Quantity
Lemon grass oil 25 mL
Diethyl ether, solvent grade 300 mL
Calcium chloride, anhydrous, granular 5–10 g
Chemicals for unsaturation tests (see 4.7A1)
Equipment:
Apparatus for steam distillation using an internal steam source 10
4.7 Qualitative Analysis.
Part A. Tests for Unsaturation
1. Bromine in Dichloromethane
Chemicals: Quantity
Dichloromethane 25 mL
Bromine 0.01 mL
To prepare a 0.1 M solution of Br2 in CH2Cl2, dissolve 0.01 mL of Br2 in 10 mL of CH2Cl2;
store the solution in a tightly stoppered container.
2. Potassium Permanganate
Chemicals: Quantity
Water, distilled 2 mL
Potassium permanganate 0.032 g
Ethanol, 95% 40 mL
11
in part.
Dissolve 0.32 g of KMnO4 in 20 mL of distilled water to give a 0.1 M aqueous solution.

4.7 Qualitative Analysis (cont.)
Part B. Test for Aldehyde Function
Chromic Acid
Chemicals: Quantity
Chromic anhydride 10 g
Sulfuric acid, concentrated 10 mL
Water, distilled 30 mL
To prepare chromic acid, add 1 g of chromic anhydride to 1 mL of concentrated H2SO4 and
stir the mixture until a smooth paste is obtained. Then cautiously dilute the paste with 3 mL
of distilled H2O and stir this mixture until a clear orange solution is obtained.
CH 5 Extraction
5.3 Base and Acid Extractions
Chemicals: Quantity
Benzoic acid 22 g 3g
Naphthalene 22 g 3g
2-Naphthol 7g 1g
4-Nitroaniline 5g 1g
Diethyl ether, solvent grade 750 mL 50 mL
Dichloromethane 400 mL 30 mL
Sodium bicarbonate, 1.25 M 200 mL 10 mL
Sodium hydroxide, 2.5 M 350 mL 10 mL
Sodium hydroxide, 6 M 750 mL 30 mL
Hydrochloric acid, 3 M 250 mL
Hydrochloric acid, 6 M 750 mL 30 mL
Hydrochloric acid, 12 M 5 mL
Sodium Sulfate, anhydrous 10 g 5g
5.4 Isolation of Trimyristin from Nutmeg
Chemicals: Quantity
Ground nutmeg 40 g 10 g
12
in part.
Diethyl ether, solvent grade 150 mL 50 mL
Acetone 50 mL 15 mL
CH 6 Chromatography
6.2 Thin-Layer Chromatography
Part A. Separation of Spinach Pigments by TLC
Chemicals: Quantity
Green leaves 10
Petroleum ether (30–60 °C) 150 mL
Ethanol, absolute 30 mL
Sodium sulfate, anhydrous 10 g
Chloroform 100 mL
Acetone 100 mL
Equipment:
Bottle, wide-mouth, for developing chamber 10
Eastman Type K301R2 Chromagram sheet or equivalent 1 sheet
Part B. Separation of Syn- and Anti-Azobenzenes by TLC
Chemicals: Quantity
Azobenzene solution in toluene, 10% 10 mL Petroleum ether (30–60
°C) 100 mL
Acetone 100 mL
Chloroform 100 mL
Equipment:
Bottle,wide-mouth, for developing chamber 10
Eastman Type K301R2 Chromatogram sheet or equivalent 1 sheet
Sunshine or sun lamp
6.3 Column Chromatography
Chemicals: Quantity
Alumina 50 g
Sand 10 g
Petroleum ether (60–80 °C) 1L
Fluorene 1g
9-Fluorenone 1g
13
in part.
Equipment:
50-mL Buret 10
Glass wool or cotton
Erlenmeyer flasks, 50-mL 30
6.4 Gas-Liquid Chromatography
Part A. Qualitative and Quantitative Analyses of a Mixture of Compounds by GLC
Chemicals: Quantity
Ethyl acetate 10 mL
n-Butyl acetate 10 mL
Ethylbenzene 10 mL
Isopropylbenzene 10 mL
Toluene 10 mL
Part B. Determining GLC Response Factors
A selection of the same chemicals required for Part A.
Equipment:
Gas chromatograph, equipped with column and recorder
Syringes, 1–10 L capacity
Syringe, gas-tight
CH 7 Stereoisomers
7.2 Separation of Diastereomeric 1,2-Cyclohexanediols
Chemicals: Quantity
1,2-Cyclohexanediol, commercial mixture of cis- and
trans-isomers ca. 1 g
trans-1,2-Cyclohexanediol, 98% ca. 1 g
Acetone 20 mL
Petroleum ether, bp 60–80 °C 75 mL
2-Propanol 25 mL
Iodine 1g
Equipment:
Eastman Type K301R2 Chromagram sheet or equivalent 1 sheet
Bottle, wide-mouth, for developing chamber 10
7.3 Isomerization of Dimethyl Maleate to Dimethyl Fumarate

14
in part.
Chemicals: Quantity
Dimethyl maleate 15 mL 5 mL
Bromine in dichloromethane, 0.6 M 20 mL
7.3 Isomerization of Dimethyl Maleate to Dimethyl Fumarate (cont.)
Chemicals: Quantity
Dichloromethane 10 mL 5 mL Ethanol, 95% 50 mL 10 mL
Cyclohexene 10 mL 5 mL
Equipment:
100-watt unfrosted light bulb and socket 1
7.4 Properties of the Enantiomeric Carvones.
Part A. Properties of the Enantiomeric Carvones
Chemicals: Quantity
Spearmint and/or caraway seed oil 150 mL (140 g)
(Suppliers of the essential oils are listed in the Thomas
Register or in Chem Sources U.S. A. One vendor is Pfaltz
& Bauer, Inc.)
To prepare a 0.1 M solution of Br2 in CH2Cl2, dissolve 0.01 mL of Br2 in 10 mL of CH2Cl2;
keep the solution in a tightly stoppered container.
Equipment:
Manometer
Gas chromatograph
Polarimeter
Part B. Formation of Carvone 2,4-Dinitrophenylhydrazone
Chemicals: Quantity
Spearmint and/or caraway seed oil 6 mL 2,4-Dinitrophenylhydrazine
6 g Sulfuric acid, concentrated 30 mL
Ethanol, 95% 350 mL
Ethyl acetate 50 mL
7.6 Resolution of Racemic 1-Phenylethanamine

Chemicals: Quantity
15
in part.
1-Phenylethanamine, racemic 125 g

Methanol 3.0 L
(+)-Tartaric acid 156 g
7.6 Resolution of Racemic 1-Phenylethanamine (cont.)

Chemicals: Quantity
Sodium hydroxide, 14 M 80 mL
Ether, solvent grade 1.5 L
Sodium chloride 55 g
Sodium sulfate, anhydrous 30 g
Equipment:
Polarimeter
CH 9 Alkanes
9.2 Free-Radical Chain Chlorination of 1-Chlorobutane
Chemicals: Quantity
1-Chlorobutane 50 mL 5 mL
Sulfuryl chloride 20 mL 2 mL
1,1’-Azobis(cyclohexanenitrile) 2.0 g 0.2 g
Sodium carbonate, 0.5 M (100 g of Na2SO4/4 L of
solution) 100 g 10 g
Sodium sulfate, anhydrous 50 g 5g
Sodium chloride solution (brine) 300 mL 20 mL
Equipment:
Glass wool, Pyrex
Gas trap 10 10
9.3 Relative Rates of Free-Radical Chain Bromination
Chemicals: Quantity
Toluene 5 mL
Ethylbenzene 5 mL
Isopropylbenzene 5 mL
tert-Butylbenzene 5 mL
16
in part.
Cyclohexane 5 mL
Methylcyclohexane 5 mL
Bromine in dichloromethane, 1 M 70 mL
Equipment:
100- or 150-watt unfrosted light bulb and socket 1
CH 10 Alkenes
10.2 Dehydrohalogenation of Alkyl Halides
Part A. Elimination with Alcoholic Potassium Hydroxide
Chemicals: Quantity
Potassium hydroxide in 1-propanol, 4 M 250 mL 25 mL
2-Bromo-2-methylbutane 25 mL 10 mL
Part B. Elimination with Potassium tert-Butoxide
Chemicals: Quantity
Potassium tert-butoxide in anhydrous tert-butyl

alcohol, 1 N 250 mL
2-Bromo-2-methylbutane 25 mL
Qualitative Tests
Chemicals: Quantity
Cyclohexene 2g
Bromine in dichloromethane solution (see Section 4.7A1)
Baeyer test (see Section 4.7A2)
10.3 Dehydration of Alcohols
Part A. Dehydration of 4-Methyl-2-pentanol
Chemicals: Quantity
4-Methyl-2-pentanol 40 mL
Sulfuric acid, 9 M (50:50 concentrated H2SO4:H2O) 25 mL
Potassium carbonate, anhydrous 20 g

Part B. Dehydration of Cyclohexanol
Chemicals: Quantity
17
in part.
Cyclohexanol 50 mL 10 mL
Sulfuric acid, 9 M (50:50 concentrated H2SO4:H2O) 25 mL 5 mL
Potassium carbonate, anhydrous 20 g 2g

Qualitative Tests
Chemicals: Quantity
Cyclohexene 2g
Bromine in dichloromethane solution (see Section 4.7A1)
Qualitative Tests (cont.)
Chemicals:
Baeyer test (see Section 4.7A2)
10.5 Addition of Hydrobromic Acid to Alkenes
Part A. Addition of Hydrogen Bromide to 1-Hexene
Chemicals: Quantity
1-Hexene 30 mL 5 mL
Hydrobromic acid, concentrated 140 mL 20 mL
Methyltrioctylammonium chloride 10 g 1.5 g
Petroleum ether (30–60 °C) 150 mL 10 mL
Sodium bicarbonate, 10% (50 g of NaHCO3/500 mL
of solution) 300 mL 10 mL
Sodium sulfate, anhydrous 20 g 2g
Part B. Qualitative Analysis of Alkyl Halides
1. Silver Nitrate Test
Chemicals: Quantity
Silver nitrate 0.4 g
Ethanol, 85% 20 mL
To prepare a 0.1 M solution of AgNO3 in ethanol, dissolve 0.4 g of AgNO 3 in 20 mL of 95% ethanol;
store the solution in a dark bottle.
2. Sodium Iodide Test
Chemicals: Quantity
Sodium iodide 1.5 g
Acetone 10 mL
To prepare a 1 M solution of NaI in ethanol, dissolve 1.5 g of NaI in 10 mL of acetone;
store the solution in a dark bottle.
10.6 Bromination of Alkenes
18
in part.
Part A. Bromination of (E)-Stilbene

Chemicals: Quantity
(E)-Stilbene 9g 1.8 g
Dichloromethane 125 mL 25 mL
Bromine in dichloromethane, 1 M 50 mL 10 mL
Part B. Bromination of (E)-Stilbene: The Green Approach
Chemicals: Quantity
(E)-Stilbene 6g 1.5 g
Hydrobromic acid, concentrated 15 mL 5 mL
Hydrogen peroxide, 30% 10 mL 3 mL
Ethanol, 95% 140 mL 35 mL
Xylene 100 mL 25 mL
Equipment: Quantity
Pipet, 1-mL, graduated 10 10
Pipet, 2 mL, graduated 10
Part C. Bromination of (E)-Cinnamic Acid
Chemicals: Quantity
(E)-Cinnamic acid 8g 1.5 g
Acetic acid, glacial 100 mL 15 mL
Pyridinium tribromide 17.6 g 3.3 g
Sodium bisulfite, 10% aqueous 50 mL 10 mL
1:1 95% EtOH:H2O 200 mL 40 mL
10.7 Hydration of Norbornene
Chemicals: Quantity
Sulfuric acid, concentrated 20 mL
Norbornene 10 g
19
in part.
Another random document with
no related content on Scribd:
A BABY TOWER,
FOOCHOW
BOTTLE SELLER
AND
HOSPITAL PATIENT.
The hospitals of England and China have evidently many things in

common. Inside the compound of the English Presbyterian Medical
Mission of Swatow, the patients buy their bottles of the vendor as
they if were patients of Guy’s or St. Bartholomew’s. A similar incident
is to be witnessed in Smithfield any day of the week. It may be
mentioned that the hospital of this particular Medical Mission is
nearly the largest in the East. In times of stress it accommodates
four hundred patients, and in the proportion of its cures is one of the
most successful in the world.
BOTTLE SELLER
AND
HOSPITAL PATIENT
THE DYING COOLIE.
Perhaps because benevolence and charity are the objects of guilds,

there is very little of the personal element in either. Personal
kindliness and care for the sick and dying do not characterise the
people of China. If a man is sick to death he is of no more use, and
why should time and care be wasted on him? This coolie in the
picture was one of Mrs. Bishop’s carriers, who fell sick by the way,
and though he had been a companion of the other men for many
days, they had no care for him when he fell sick, and Mrs. Bishop
was laughed at for taking the trouble to wet a handkerchief to lay on
the feverish forehead of a man who was of “no more use.”
THE DYING COOLIE
THE MODE OF SEPULCHRE
THROUGHOUT
SOUTHERN CHINA.
A horseshoe-shaped excavation is made in a hillside facing south,

the whole construction being faced with stone. There is in this mode
of arranging graves a similarity to that adopted by the Etruscans.
THE MODE OF SEPULCHRE
THROUGHOUT
SOUTHERN CHINA
COFFINS KEPT
ABOVE GROUND.
So careful is the Chinaman about his burial, that the date and place
of a funeral is not fixed until the geomancers have decided as to
both. Sometimes the coffins with their inmates remain above ground
for months, and even years, waiting for the professional decision as
to a favourable day. In such cases, where the friends are able, every
care is taken of them, incense being daily burned before them. It was
no uncommon thing for Mrs. Bishop, on her journey in Sze Chuan, to
have to sleep in a room where a coffin was stored, waiting the day of
its interment, incense burning and other religious rites being daily
performed in front of it. To prevent mischief owing to the retention of
bodies above ground for so long a time, the coffins are built of very
thick wood, the bodies are placed in lime, the joints of the coffin are
cemented, and the whole covered with varnish.
COFFINS KEPT
ABOVE GROUND
THE TEMPLE OF
THE GOD OF LITERATURE
AT MUKDEN.
Mukden is the capital of Manchuria, the Northern Province. In every

province of the Empire the God of Literature stands highest in the
Chinese Pantheon, and it is interesting to note that the God of War
stands low, though in China, as in other countries, we know women
are devoted to his worship. In no country of the world does literature
stand in such high estimation; by means of it the poorest man may
climb to the highest post in the Empire. Nothing so helps a man to a
career as a knowledge of the literature of his country. Reverence for
it has become a superstition, and societies exist for collecting waste
paper and saving any writing from indignity by burning it in furnaces
erected for the purpose in every town.

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Section 2.

Solution Manual for Experimental Organic Chemistry

Full link download

SECTION 2. CHEMICALS AND SPECIAL EQUIPMENT BY CHAPTERS

Benzoic acid 0.60 g

Petroleum ether (bp 60–80 °C) 30 mL

Impure benzoic acid 10 g 1.0 g

Filter aid (Celite) 10 g 2.0 g

3-Phenylpropanoic acid 0.2 g

Salicylic acid 0.2 g

3,5-Dinitrobenzoic acid 0.2 g

or electric melting point apparatus 1

are two or three students per compound in the lab.

CH 4 Liquids: Distillation and Boiling Points

Compounds for Boiling Point Knowns and Unknowns

4.3 and 4.4 Simple and Fractional Distillation

Dissolve 0.32 g of KMnO4 in 20 mL of distilled water to give a 0.1 M aqueous solution.

Diethyl ether, solvent grade 750 mL 50 mL

Sodium bicarbonate, 1.25 M 200 mL 10 mL

Sodium hydroxide, 2.5 M 350 mL 10 mL

Sodium hydroxide, 6 M 750 mL 30 mL

Hydrochloric acid, 3 M 250 mL

Hydrochloric acid, 6 M 750 mL 30 mL

Sodium Sulfate, anhydrous 10 g 5g

5.4 Isolation of Trimyristin from Nutmeg

Diethyl ether, solvent grade 150 mL 50 mL

trans-1,2-Cyclohexanediol, 98% ca. 1 g

Petroleum ether, bp 60–80 °C 75 mL

Eastman Type K301R2 Chromagram sheet or equivalent 1 sheet

Bottle, wide-mouth, for developing chamber 10

7.3 Isomerization of Dimethyl Maleate to Dimethyl Fumarate

7.6 Resolution of Racemic 1-Phenylethanamine

1-Phenylethanamine, racemic 125 g

7.6 Resolution of Racemic 1-Phenylethanamine (cont.)

Sodium sulfate, anhydrous 50 g 5g

Sodium chloride solution (brine) 300 mL 20 mL

9.3 Relative Rates of Free-Radical Chain Bromination

100- or 150-watt unfrosted light bulb and socket 1

Potassium tert-butoxide in anhydrous tert-butyl

Potassium carbonate, anhydrous 20 g

Potassium carbonate, anhydrous 20 g 2g

Part A. Bromination of (E)-Stilbene

Hydrobromic acid, concentrated 15 mL 5 mL

Hydrogen peroxide, 30% 10 mL 3 mL

Ethanol, 95% 140 mL 35 mL

Pipet, 1-mL, graduated 10 10

Pipet, 2 mL, graduated 10

Part C. Bromination of (E)-Cinnamic Acid

(E)-Cinnamic acid 8g 1.5 g

Acetic acid, glacial 100 mL 15 mL

Pyridinium tribromide 17.6 g 3.3 g

Sodium bisulfite, 10% aqueous 50 mL 10 mL

1:1 95% EtOH:H2O 200 mL 40 mL

10.7 Hydration of Norbornene

The hospitals of England and China have evidently many things in

Perhaps because benevolence and charity are the objects of guilds,

A horseshoe-shaped excavation is made in a hillside facing south,

Mukden is the capital of Manchuria, the Northern Province. In every

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