PDF Lab Manual For Organic Chemistry A Short Course 13Th 13Th Edition David J Hart Ebook Full Chapter

Lab Manual for Organic Chemistry A
Short Course 13th 13th Edition David J.

Hart
Visit to download the full and correct content document:
https://textbookfull.com/product/lab-manual-for-organic-chemistry-a-short-course-13th
-13th-edition-david-j-hart/
More products digital (pdf, epub, mobi) instant
download maybe you interests ...
Study Guide and Solutions Manual Intl Edition for Hart

Hadad Craine Hart s Organic Chemistry a Brief Course
International Edition 13th David J. Hart
https://textbookfull.com/product/study-guide-and-solutions-
manual-intl-edition-for-hart-hadad-craine-hart-s-organic-
chemistry-a-brief-course-international-edition-13th-david-j-hart/
Organic Chemistry I Lab Manual 18th Edition David

Moderelli
https://textbookfull.com/product/organic-chemistry-i-lab-
manual-18th-edition-david-moderelli/
Chemistry 13th Edition Raymond Chang
https://textbookfull.com/product/chemistry-13th-edition-raymond-
chang/
Organic Chemistry 2nd Edition Robert J. Ouellette And

J. David Rawn
https://textbookfull.com/product/organic-chemistry-2nd-edition-
robert-j-ouellette-and-j-david-rawn/
Organic Evolution Evolutionary Biology 13th Edition
Veer Bala Rastogi
https://textbookfull.com/product/organic-evolution-evolutionary-
biology-13th-edition-veer-bala-rastogi/
Choices in Relationships 13th Edition David Knox
https://textbookfull.com/product/choices-in-relationships-13th-
edition-david-knox/
Financial Markets & Institutions (MindTap Course List)

13th Edition Jeff Madura
https://textbookfull.com/product/financial-markets-institutions-
mindtap-course-list-13th-edition-jeff-madura/
Accounting Principles, 13th Edition Jerry J. Weygandt
https://textbookfull.com/product/accounting-principles-13th-
edition-jerry-j-weygandt/
Organic Chemistry Student Study Guide and Solutions

Manual 3 ed 3rd Edition Klein David
https://textbookfull.com/product/organic-chemistry-student-study-
guide-and-solutions-manual-3-ed-3rd-edition-klein-david/
Laboratory Manual
Organic Chemistry
A Short Course
THIRTEENTH EDITION
David J. Hart
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University, Professor Emeritus
T. K. Vinod
Western Illinois University
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
This is an electronic version of the print textbook. Due to electronic rights restrictions,
some third party content may be suppressed. Editorial review has deemed that any suppressed
content does not materially affect the overall learning experience. The publisher reserves the right
to remove content from this title at any time if subsequent rights restrictions require it. For
valuable information on pricing, previous editions, changes to current editions, and alternate
formats, please visit www.cengage.com/highered to search by ISBN#, author, title, or keyword for
materials in your areas of interest.
© 2012 Brooks/Cole, Cengage Learning ISBN-13: 978-1-111-42584-5
ISBN-10: 1-111-42584-1
ALL RIGHTS RESERVED. No part of this work covered by the
copyright herein may be reproduced, transmitted, stored, or Brooks/Cole
used in any form or by any means graphic, electronic, or 20 Davis Drive
mechanical, including but not limited to photocopying, Belmont, CA 94002-3098
recording, scanning, digitizing, taping, Web distribution, USA
information networks, or information storage and retrieval
systems, except as permitted under Section 107 or 108 of the Cengage Learning is a leading provider of customized
1976 United States Copyright Act, without the prior written learning solutions with office locations around the globe,
permission of the publisher. including Singapore, the United Kingdom, Australia,
Mexico, Brazil, and Japan. Locate your local office at:
www.cengage.com/global
For product information and technology assistance, contact us at Cengage Learning products are represented in
Cengage Learning Customer & Sales Support, Canada by Nelson Education, Ltd.
1-800-354-9706
To learn more about Brooks/Cole, visit
For permission to use material from this text or product, submit www.cengage.com/brookscole
all requests online at www.cengage.com/permissions
Further permissions questions can be emailed to Purchase any of our products at your local college
permissionrequest@cengage.com store or at our preferred online store
www.cengagebrain.com
Publisher: Mary Finch

Acquisitions Editor: Chris Simpson
Assistant Editor: Jon Olafsson
Editorial Assistant: Laura Bowen
Marketing Manager: Barb Bartoszek
Marketing Coordinator: Julie Stefani
Art Director: John Walker
Production Manager: Michelle Clark
Manufacturing Buyer: Judy Inouye
Cover image: © Steve Taylor/Getty Images
Printed in the United States of America

1 2 3 4 5 6 7 14 13 12 11 10
Contents
Preface v
Introduction: To the Student viii
1. Melting Point Determination: Purity and Identity of Crystalline

Organic Compounds 1
2. Recrystallization: Purification of Crystalline Organic Compounds 11
3. Distillation: Separation and Purification of Organic Liquids 23
4. Extraction: A Separation and Isolation Technique 33
5. Isolation of Natural Products: Caffeine and Eugenol 47
Chemistry at Home: Spice Essences 57
6. Chromatography: Column, Thin-Layer, Gas-Liquid, and Paper 59
Chemistry at Home: Food Dyes and Marking Pens 77
7. Conformations of Alkanes and Cycloalkanes: An Exercise with Molecular Models and

Computer Modeling 79
8. Preparation of Alkenes from Cyclohexanol or 2-Methyl-2-butanol, and Tests for

Unsaturation 107
9. Cis-Trans Isomerism in Alkenes: Models and Experiments 123
10. Cycloadditions: The Diels-Alder Reaction 133
11. Electrophilic Aromatic Substitution 149
12. Stereoisomerism: Principles Illustrated with Molecular

Models, Computer Modeling and Experiments 169
13. Alkyl Halides: Structure and Reactivity in Nucleophilic Substitutions 199
14. The Hydroxyl Group: Reactions of Alcohols and Phenols 215
15. Reactions of Aldehydes and Ketones 231
16. Oxidation of Alcohols and Reduction of Ketones 253
17. Oxidation of Aldehydes to Carboxylic Acids: A Green Chemistry Experiment 265
18. Two Ways to Synthesize a Carboxylic Acid 271
iii
iv Contents
19. Reactions of Carboxylic Acids and Their Derivatives 283
Chemistry at Home: Eggshells and Vinegar 301
20. Esters: Synthesis and Saponification of Methyl Benzoate 303
Chemistry at Home: Saponification Is Making Soap 315
21. Synthesis of Aspirin (Acetylsalicylic Acid) 319
22. Amines and Diazonium Compounds 327
23. Preparation of Sulfanilamide: A Multistep Synthesis 341
24. Dyes and Dyeing 351
Chemistry at Home: Natures’s Indicators and What They Indicate 366
25. Infrared and NMR Spectroscopy 369
26. Synthesis of a Heterocycle: 2-Amino-4,6-dimethylpyrimidine 379
27. Storage and Release of Light Energy: Benzopinacol and Luminol 387
28. Synthetic Polymers 395
29. Fats and Oils; Soaps and Detergents 409
Chemistry at Home: Soap and Talcum Powder 421
30. Reactions of Carbohydrates 423
Chemistry at Home: Where’s the Starch? 439
31. Amino Acids and Proteins 441
Chemistry at Home: Enzymes Are Nature’s Catalysts 461
Appendix A Some Useful Atomic Weights 463
Appendix B Boiling Points and Densities of Some Common Organic Liquids 463
Appendix C Concentrations of Common Reagents 463
Appendix D Preparation of Special Reagents 464
Appendix E Chemicals Required for Each Experiment 465
Appendix F Suggested Equipment for Each Student 481
Index 483
Preface
This laboratory manual is designed for a short introductory course in organic chemistry. It is ideal
for a one-semester or a one- or two-quarter course. Most of the experiments can be completed by
a beginner in a single three-hour laboratory period, and some in considerably less time. Many
experiments have multiple parts that can easily be adapted to a two-hour period, if necessary.
The manual consists of thirty-one experiments, offering instructors a wide selection from
which to choose. In addition, those experiments with multiple parts allow instructors flexibility
in choosing experiments particularly suited to their own students, facilities, and schedules. For
further alternatives, nearly half the experiments offer optional microscale procedures. The lab
manual also includes a set of eight experiments under the heading of Chemistry at Home that
students can do outside a laboratory setting.
Among the many features of this manual is the useful combination of varied experiments:
technique experiments; preparative experiments; experiments that illustrate reactions of and tests
for various functional groups; and general-interest, or practical, experiments illustrating
applications of organic chemistry. In this edition we have included an experiment for an eco-
friendly oxidation of aldehydes to carboxylic acids thus introducing students to the concepts of
Green Chemistry. Also in this edition is the inclusion of Pre-Lab Exercises, a set of questions
following each experiment which instructors may utilize and include as part of the required pre-
lab write up or use as pre-lab quizzes to ascertain student preparedness to successfully carry out
the experiment. Immediately following the Pre-Lab exercise of every experiment, report sheets on
perforated paper help students take notes in an orderly manner. Questions at the end of the report
enable students to reinforce what they have learned from the experiment.
For the instructor’s convenience, the appendices include instructions for preparing special
reagents and complete lists of the chemicals required for each experiment and their quantities
per ten students.
Organization
The experiments are organized as follows: The first six illustrate common laboratory techniques.
The next sixteen give the student experience with some important reactions of the common
functional groups. This sequence parallels the order in which these groups are discussed in the
accompanying text (Hart, Organic Chemistry: A Short Course, 13th edition) and approximates the
order in most brief texts. Next comes a simple multistep synthesis, followed by experiments on
practical applications, on spectroscopy, and on biomolecules (or their analogs). Chemistry at Home
experiments are located at the end of experiments to
which they are related.
Unique to this manual are Experiments 7 and 12—which give the student experience in
manipulating molecular models in the context of conformational analysis and stereochemistry,
and subsequently giving them an opportunity to verify what they learned about strain energy and
conformations by having them perform molecular modeling (mechanics) calculations using
commercially available modeling programs. Molecular models are also used in Experiment 9 in
conjunction with experimental sections to highlight the configurational aspects and reactivity
patterns of cis-trans isomers. In Experiment 17 and 18, the student synthesizes the same
compound by three different methods and consequently learns that one’s objectives can be
achieved through more than one approach.
vi Preface
The Thirteenth Edition
The order of experiments in the thirteenth edition follows closely the order in which topics are
introduced in the accompanying text. Experiment 11 (Electrophilic Aromatic Substitution) uses
a discovery format, although it can be carried out in the traditional manner at the instructor’s
discretion. In the discovery format, students make individual contributions to a common data
pool, from which conclusions can be drawn about substituent directing effects (Part A) and
activating effects (Part B). Either Part A or Part B can be carried out within one
3-hour lab period. Experiment 17, describing an eco-friendly protocol for a convenient
oxidation of aldehydes to carboxylic acids, is a new experiment included in this edition.
Experiments 1, 4, 5, 7, 8, 10, 12, 14, 15, and 22 have been revised significantly, including
some changes in existing experiments, some additions, and some deletions.
Microscale A large number of undergraduate teaching laboratories have converted to microscale

Experiments techniques for reasons of laboratory safety, economy of scale, and reduction of waste-
disposal problems. As in the previous four editions, this edition contains both macroscale
and microscale experiments. Microscale procedures are included in Experiments 2, 4, 8-11,
13, 15-21, 23, 26, and 27.
The procedures for the microscale experiments are based on the glassware designed and
developed by Mayo, Pike and Forbes.* Most of these experiment, however, can also be
adapted to the glassware designed for Williamson’s text,** and many can be run in readily
available glassware and do not require a special kit. The microscale experiments that can be
run without special glassware are Experiments 2 Part A, 4, 9 Part B (Sec. 2), 10, 11, 15, 16
Part B, 21, 23, 26, and 27 Part A.
Chemistry A thirteenth edition contains a set of eight experiments that students can do outside the
at Home laboratory. These experiments are located at the end of Experiments 5, 6, 19, 20, 24, 29, 30
and 31. Each one contains a brief introduction, a list of materials needed (all of which are
readily obtained household items), a procedure, some questions for thought, some suggestions
for additional explorations, and some suggested reading materials. No report form is provided
since these experiments are meant to be exploratory and open-ended. The instructor may wish
to assign these experiments, use them as a springboard for other laboratory or classroom
activities, or simply encourage students to try them out.
Safety and As in previous editions, safety is emphasized in this edition. Readily identifiable “Cautions”
Waste Disposal advise students and instructors of potential hazards and precautionary measures. Safer
Instructions heating methods have been substituted for oil baths and Bunsen burners when possible. Safety
and environmental considerations have prompted us to include the suggested waste
disposal directions to the experiment procedures. Students are clearly instructed to dispose of
both organic and aqueous wastes in appropriately labeled waste containers. Under no
circumstance should aqueous waste from experiments be disposed of in the sink flushing it
with large amounts of water. Although chemical experimentation always carries some risk
with it, most of these experiments have been used safely with thousands of students for more
than 30 years. The microscale experiments offer additional safety advantages because they
involve decreased exposure to toxic substances and use smaller quantities of flammable
solvents. With care, common sense, and good judgment, all of these experiments should be
safe, even in the hands of beginners.
*Mayo, D. W., Pike, R. M., and Forbes, D. C., Microscale Organic Laboratory: with Multistep and
Multiscale Syntheses, 5th ed., John Wiley & Sons: Hoboken, 2011.
**Williamson, K. L., and Masters, K. M., Macroscale and Microscale Organic

Experiments, 6th ed., Brooks/Cole, Cengage Learning: Belmont, 2011.
Preface vii
The Chemistry at Home experiments are as safe as any normal activity carried out in the home
and do not, therefore, require special safety instructions. However, students should be reminded to
pay attention to the cautions on the labels of the household products they use and in general to
behave sensibly around kitchen appliances. In two of the experiments, additional cautions are
explicitly given because pf the nature of the household products used.
Safety Note It is assumed throughout this manual that each instructor is thoroughly familiar with ordinary
safety precautions involved with solutions he or she prepares for students. If students, lab
assistants, or untrained personnel are used to prepare these solutions, the instructor is solely
responsible for the safety of the students who use the laboratory manual; even though safety
precautions are featured as required in each experiment, they are not intended as a substitute for
the instructor’s directions and supervision.
Acknowledgments
Reviewers of previous editions of this manual have found that there is a “good representative
selection of well-described experiments that work well when performed by beginners” and that
“in general this manual requires less costly materials and relatively safe procedures and materials
when compared to other lab manuals.” We hope that users of previous editions and new users of
this one will continue to find these virtues in the manual. Suggestions for improvement are
always welcome and should be sent to Dr. T. K. Vinod, Department of Chemistry, One
University Circle, Western Illinois University, Macomb, IL 61455.
DAVID J. HART
THE OHIO STATE UNIVERSITY
LESLIE E.CRAINE
CENTRAL CONNECTICUT STATE UNIVERSITY
HAROLD HART
MICHIGAN STATE UNIVERSITY
DR. T. K. VINOD
WESTERN ILLINOIS UNIVERSITY
Introduction: To the Student
Aims of Laboratory Work
The experiments in this book illustrate many of the reactions discussed in your text. When you
perform a reaction in the laboratory, it should become more vivid to you and therefore easier to
conceptualize and remember.
Before each set of experiment directions, you will find a brief discussion of the chemistry
that the experiment illustrates. It is important that you read and understand these discussions
before doing the experiment. You may find it helpful to look up the particular reaction in your
text and read about it there, as well. There is not much point in performing an experiment
without really understanding what you are doing.
The primary aim of laboratory work in this course is to illustrate the chemical reactions and
properties of molecules discussed in lecture and to help you learn them. We hope that you will
also find some of the experiments fun to do and that you will be encouraged to try your hand at
some of the new Chemistry at Home experiments as well.
General Laboratory Instructions and Pre-Lab Preparations
Learning experimental chemistry efficiently requires one to arrive at the laboratory prepared. Be
sure to read the experiment directions before your scheduled laboratory period. Familiarize
yourself with the equipment and procedure before you enter the laboratory. If you do not
understand them, or if you have some questions about the chemistry involved in an experiment,
ask your instructor directly for a reliable response.
Many students come to the laboratory ill-prepared to perform the experiment and consider
it perfectly acceptable to carry out their work by following a given experimental procedure as a
recipe to obtain their final desired result or product. Blindly following a procedure (often
asking oneself in the middle of the experiment, what do I add next? or what do I do next?)
invariably results in adding or doing the wrong thing at the wrong time. The ill consequences
of such an approach in the laboratory can result in having to re-do the experiment, not getting
the desired product/result at the end, and, even worse, creating accidents that can potentially
hurt the student and other occupants of the lab.
In order to enhance the learning experience and enjoyment of a laboratory experience,
instructors often require students to complete a detailed pre-lab write-up prior to attending the
laboratory, thus forcing the students to read the theory and practical aspects of the experiment.
Individual instructors vary in their preference for the type of laboratory notebook to be used, but
universally all instructors prefer a bound notebook with entries made in ink. The pre-lab write-
up includes the title of the experiment, purpose, chemical equations in case of preparative
experiments, reagents and amounts used, a detailed procedure, and, finally, answers to any
assigned pre-lab questions.
Following each experiment, you will find a set of questions under the heading of Pre- Lab
Exercise. Your instructor may assign all or some of these questions as part of your pre- lab write-up
or may choose to use these questions as a pre-laboratory quiz to ascertain your preparedness to do
that particular experiment. In any case, by answering these questions, you will able to comprehend
the underlying concepts, both theoretical and practical, of the experiment and will also be able to
assess your preparedness to successfully complete the experiment in the allotted time.
viii
Introduction ix
While performing the experiment, students must pay special attention to all safety precautions
noted in this manual and those announced in class by your instructor. Laboratory work should not
be messy. Keep your bench reasonably neat. Wear a lab apron to protect your clothes. Many of the
experiments in this book require the use of clean and dry apparatus. For this reason, you should
clean all soiled apparatus at the end of each experiment so that it will be dry and ready for use
when next needed. However, do not waste time drying labware that will be used with water or
aqueous solutions.
Record-Keeping
It is necessary to keep a record of the results obtained in an experiment so that you can refer to
them later. To assist you in your record-keeping, a report form is included after each experiment.
The first part of each form has a place for you to record your observations and data. Complete this
part as you perform an experiment, when results are fresh in your mind. Record what you observe,
not what you think you ought to observe. If an experiment does not work the way it is supposed to,
why not drop us a line and tell us about it? Perhaps we can figure out what happened and improve
the experiment in the next edition of this manual.
The second part of each report sheet contains short-answer questions that relate directly to the
experiment. They are intended to reinforce what you should have learned from the experiment.
Often, answering these questions may simply involve writing an equation or a brief explanation of
the reactions performed. A file of the corrected reports should be helpful in your study of organic
chemistry.
Safety
Though a chemical laboratory can be a fun and exciting place where students can validate the
theories and concepts that they learned in their lecture courses, it can also be a dangerous place to
work if one is not familiar with the fundamentals of laboratory safety. This is especially so in an
organic chemistry laboratory where students often work with flammable, corrosive, toxic, and
sometimes even carcinogenic (cancer-producing) substances. Many of the chemicals are also
volatile and can easily get into the air you breathe or be easily absorbed through skin when
accidentally spilled on oneself. In addition to these potential dangers, many of the experimental
procedures in an organic chemistry laboratory require the use of glassware that is easily broken,
and this poses additional danger to the student. Negligence on the part of one student can affect the
well-being of all of his/her labmates. Thus, safety in the laboratory is of paramount importance and
everyone is expected to follow all of the safety regulations of the laboratory. Listed below are a
few precautions that you should take to avoid accidents in an organic chemistry laboratory. In
addition to these listed precautions, your instructor may have additional precautions and a list of
do’s and don’ts that you will need to follow while in the laboratory.
1. Wear eye protection at all times. Locate the eye-wash stations and know how to use them. If
you do not wear prescription glasses, wear safety glasses. If you wear contact lenses, wear
prescription glasses, preferably, or clear safety glasses when you work in the laboratory. It is a
standard rule that students may not work in the laboratory without eye protection.
2. Locate all fire extinguishers, fire blankets, and safety showers and know how to use them. Fire
is a particular hazard in the organic laboratory because commonly used solvents such as ether,
alcohol, and acetone are flammable. Light burners only when you are required to use them,
and note those experiments that do not permit the use of lit burners in the laboratory. To
ensure the safety of yourself and those around you, closely follow instructions regarding the
use of burners. Smoking in the laboratory is strictly forbidden.
3. Locate the first aid kits.
x Introduction
4. Report all accidents such as cuts, burns, spilled chemicals, and so on to your
instructor. He or she can help you with minor first aid and will get emergency help
quickly, if necessary.
5. Be aware of what is going on around you. In this way, you may avoid being a
victim of your neighbor’s accident.
6. Do not perform unauthorized experiments. They can be dangerous to your own and your
labmates’ health and safety.
7. Closely follow your instructor’s directions.
In addition to accidents, there are other laboratory hazards to be aware of and guard
against:
8. Avoid breathing the vapors of volatile solvents. Some organic solvents, such as
halogenated hydrocarbons, may be toxic or carcinogenic. If the use of such solvents
cannot be avoided altogether, they should be used only in the laboratory hood or in
a well-ventilated laboratory.
9. Avoid contact of chemicals with your skin, eyes, and clothing. If you accidentally spill
chemicals on your body, wash the affected area with copious amounts of water. Clean up
of chemical spillage on the bench or floor must only be undertaken after the instructor is
informed and preferably under his/her supervision. Handle corrosive chemicals (strong
acids, bases, bromine and others) with extreme care. Do not taste chemicals.
10. Do not bring food or drink into the laboratory because they might accidentally
come in contact with toxic chemicals.
11. Dispose of chemicals in proper containers, according to directions from your instructor.
Ordinarily, organic chemicals are not washed down sink drains but must be carefully
disposed of in a manner that is safe and minimizes environmental pollution. Instructions
for proper waste disposal are given after each experiment procedure as necessary. In
general, common inorganic acids and bases can be neutralized and washed down the
drain. Some nonhazardous water-soluble wastes can be diluted with water and washed
down the drain. Halogenated solvents and combustible solvents should be placed in
separate waste containers. Other chemicals may need specific treatment before being
disposed of in waste containers or flushed down the drain. Your instructor will inform
you of any alternative or special procedures to be followed.
12. Keep a neat, uncluttered laboratory bench. You are less likely to break glassware or spill
chemicals if your work area is kept orderly. Also, do not fool around or talk excessively
about nonchemical subjects. Accidents are less likely to happen if you pay attention to
what you are doing.
13. Wear appropriate attire when working in the lab. As a protection against spilled
chemicals or broken glass you are required to wear appropriate clothing, such as long
pants and closed-toed shoes, while working in the lab. You are not allowed to work in the
laboratory wearing shorts, skirts and open-toed shoes. To protect yourself and your
clothing, you may choose to wear a lab coat or an apron. Use of disposable gloves while
handling chemicals is also highly encouraged.
Introduction xi
Do not dispose of any chemical waste in the sink unless specifically instructed to
do so by your instructor.
To summarize all these do’s and don’ts: When working in the laboratory, try at all
times to exercise common sense, good judgment, and consideration for others.
You, the student, are entitled to know the hazards associated with the chemicals
with which you will be working. Although this manual provides the essential
information, the chemistry department at your school or your instructor should have a
file of Material Safety Data Sheets (MSDSs) containing additional information
available for you to examine.
xii Introduction
Some examples of commonly used glassware
Introduction xiii
EXPERIMENT
1 Melting Point Determination:

Purity and Identity of Crystalline
Organic Compounds
1 How Are Melting Points Used?
Most crystalline organic compounds have characteristic melting points that are sufficiently low
(50–300°C) to be conveniently determined with simple equipment. Organic chemists routinely
use melting points (a) to get an indication of the purity of crystalline compounds and (b) to help
identify such compounds.
The melting point of a pure crystalline substance is a physical constant or property of that
substance. A physical property of a substance is one that is intrinsic to a given substance in its
pure form. Pure crystalline compounds usually have a sharp melting point. That is, the melting
point range—the difference between the temperature at which the sample begins to melt and
the temperature at which the sample is completely melted—is small (narrow). Impurities, even
when present in small amounts, usually lower the melting point and broaden the melting point
range. A wide melting point range (more than 5°C) usually indicates that the substance is
impure; a narrow melting point range (0.5–2°C) usually indicates that the substance is fairly
pure. However, there are some exceptions to both of these generalizations. Small differences in
melting point (on the order of 2–3°C) may also result from variations in technique, thermometer
accuracy, and the experience of the person doing the melting point determination.
Melting points can be used in the following way to help identify a compound. Say a sharp-
melting, unknown substance X is suspected of being identical to some known substance A. If
the two are identical, they should have the same melting point. Thus if A is reported in the
chemical literature to have a melting point significantly different from that observed for X, we
can be quite certain that X does not have the same structure as A. On the other hand, if A is
reported to have a melting point within a few degrees of that observed for X, the two substances
may be identical (the small difference being due to variations in technique or purity).
To make certain that X and A are identical, one can determine the mixture melting point—
that is, the melting point of a mixture of X and A (when a sample of A is available). If X and A
are identical, the mixture should have the same melting point as X or A alone. On the
other hand, if X and A are not the same substance (even though they separately have the same
melting point), then a mixture of the two usually has a lower melting point and a broader
melting point range than either substance alone. This is because each substance acts as an
impurity in the other.
To summarize, if a crystalline substance is pure, its melting point range is likely to be
narrow. If two samples have identical structures, their mixture melting point is not depressed
and the melting point range is not broadened.
2 Experiment 1 Melting Point Determination: Purity and Identity of Crystalline Organic Compounds
2 General Technique for Melting Point Determination
To determine the melting point of a crystalline substance, we introduce a small amount of the
finely powdered material into a thin-walled capillary tube that is sealed at one end. The
capillary tube is inserted into a melting point apparatus and heated. Two temperatures are
recorded: the temperature at which the substance begins to liquefy and the temperature at
which it becomes completely liquefied. The observed melting point range is the interval
between these two temperatures. The melting point is a characteristic property of a pure
chemical substance.
The observed melting point range can be influenced not only by the purity of the
material but also by the size of the crystals, the amount of material, the density of its packing
in the tube, and the rate of heating. A finite time is required to transfer heat from a hot liquid
bath or metal block through the walls of the capillary tube and throughout the mass of the
sample. When the bath or block is heated too quickly, its temperature rises several degrees
during the time required for melting to occur. This can result in an observed range that is
higher than the true one.
When the temperature of the bath or block approaches the melting point of the sample, it
is essential for good results to raise the temperature slowly and at a uniform rate, usually
about 2°C/min. The sample should be small, finely powdered, and packed tightly in a thin-
walled capillary tube of small diameter. The column of solid in the capillary tube should be
just high enough to be seen clearly during melting (about 1–2 mm).
The behavior of a material upon melting should be observed and recorded carefully.
Write, for example, “Melts sharply at 89.0–89.5°C” or “mp 131–133°C, with decomposition”
or “Discolors at 65°C; melts slowly at 67–69°C.”
3 Objectives of the Experiment
In this experiment you will determine the melting points of two different pure solids that
have approximately the same melting point range. You will then prepare a mixture of the two
substances and determine its melting point range. Finally, you will obtain a sample of an
unknown from your instructor. After you determine its melting point, you will identify the
substance by finding a mixture melting point.
4 The Melting Point Apparatus and Tubes
The two principal types of melting point apparatus commercially available today are those in
which the melting point tube is heated by an enclosed, electrically heated oil bath (Figure
1.1a) and those in which the melting point tube is heated by an electrically heated metal
block (Figure 1.1b).
Experiment 1 Melting Point Determination: Purity and Identity of Crystalline Organic Compounds 3
(a) Thomas-Hoover (b) Mel-Temp apparatus, Figure 1.1 Two

melting-point apparatus an electrically heated types of melting point
melting-point block
apparatus.
Your instructor will supply directions for the proper use of the melting point apparatus
available in your laboratory.*
5 Determination of Melting Points
Procedure Pulverize 50–100 mg of urea by crushing it with a spatula against the walls of a small (50
mL) dry beaker. It is important that the beaker be completely dry and free of moisture. A wet
pulverized sample will not only yield an erroneous lower melting point range but will also
make it difficult to fill the capillary tube with the required amount of sample for melting
point determination. Fill a melting point tube with a sample of urea by thrusting the open end
into the beaker several times. To work the plug of solid material down to the sealed end to
the tube, vigorously tap the sealed end on the table or lightly draw a file or stem of a test tube
brush across the tube held loosely in the hand. Repeat the procedure until the tube contains a
1–2 mm column of densely packed powder at the bottom. (See Figure 1.2.)
Insert the tube into the melting point apparatus and start heating. The temperature may
be allowed to rise fairly rapidly to within 15–20°C below the compound’s expected melting
point. However, during determination of the actual melting point range, the temperature
should not rise more rapidly than 1–2°C/min. Therefore, decrease the rate of heating when
the temperature is about 15°C below the expected melting point. The melting point of urea is
approximately 130°C. Record the melting point range of urea on the report sheet.
*It is recommended that beginners not use an open oil bath because of the risk of burns from hot oil. If,
for reasons of cost and availability, an open oil bath will be used, a description of this type of apparatus
can be found in Vogel’s Texbook of Practical Organic Chemistry Including Qualitative Organic
Analysis, 4th ed., Longman Scientific and Technical: England, 1987, pp. 222–227.
4 Experiment 1 Melting Point Determination: Purity and Identity of Crystalline Organic Compounds
In a similar way, determine and record the melting

point range of a sample of trans-cinnamic acid. This
compound also melts at approximately 130°C.
To demonstrate the effect of impurities on the
melting point of a pure substance, determine the melting
point range of a 50–50 mixture by weight (use about 50
mg of each compound) of urea and cinnamic acid. If time
permits, repeat the procedure with 75–25 and 25–75
mixtures. (Alternatively, your instructor may assign
different ratios to different students in the class, and each
student can use both his or her results and those of
Figure 1.2 A melting point
others.) Using midpoints of the melting point ranges, plot
the data on the report sheet. tube showing the actual size
of sample filled.
actual size
(filled)
6 Identification of an Unknown
When the melting point of an unknown substance is to be determined, you can save time if
you first obtain its approximate melting point using a rapid heating rate—say, 15–20°C/min.
Then allow the temperature of the thermometer to drop to 15–20°C below the approximate
melting point. Use a second sample of the substance to determine the melting point
accurately, with a slow heating rate of about 1–2°C/min.
Procedure Obtain an unknown sample (of one of the substances listed in Table 1.1) from your
instructor. Fill two melting point tubes with samples of the unknown. Use one tube to
determine the approximate melting point, and use the second tube to determine the melting
point more precisely, as described above. Use the data in Table 1.1 to make a preliminary
identification of your unknown. Then confirm its identity by the mixture melting point
technique: Mix about 50 mg of the unknown with an equal weight of the substance you
suspect it to be from the side shelf and determine the mixture melting point. Repeat the
procedure, if necessary, to determine with certainty the identity of the unknown. Record your
results and conclusion on the report sheet.
Experiment 1 Melting Point Determination: Purity and Identity of Crystalline Organic Compounds 5
Table 1.1 Melting points of some organic compounds
Compound mp, °C Compound mp, °C
Biphenyl 70–71 2-Naphthol 121–122

İ -Caprolactam 69–71 Benzoin 132–133
Vanillin 81–82 trans-Cinnamic acid 132–133
Glutaric acid 97–99 Urea 132–133
Dibenzothiophene 99–100 Cholesterol 148–150
Acetanilide 113–114* Salicylic acid 156–158
(±)-Mandelic acid 119–120 Benzanilide 164–166
Benzoic acid 121–122 Sulfanilamide 165–166
*If the acetanilide was recrystallized from water and not thoroughly dried, it may melt at 83–84°C.
Waste Discard your used melting point tubes in the waste glass container provided by your
Disposal instructor. Place extra solids from the mixture melting point in a solid organic waste container
provided by your instructor.
Name Section
Lab Instructor Date
PRELAB EXERCISE EXPERIMENT 1

Melting Point Determination: Purity and Identity
of Crystalline Organic Compounds
1. Define the term melting point range.
2. When determining the melting point of an unknown substance, it is a common practice to first determine a
rough melting point by quickly heating the sample followed by a careful determination of the melting point
by gradually heating the sample at the rate of 1–2°C/min. What is the advantage of this two-step
determination of the melting point?
3. What two effects do impurities have on the melting point of an organic compound?
Name Section
Lab Instructor Date
LAB REPORT EXPERIMENT 1

Melting Point Determination: Purity and Identity
of Crystalline Organic Compounds
Determination of Melting Points
1. Record the observed melting points in the table.
Melting Point, °C
Compound Start Finish Midpoint
Urea
Cinnamic acid
50–50 mixture
75–25 mixture
25–75 mixture
2. Graph the midpoints of the melting point ranges of urea, cinnamic acid, and mixtures of the two.
Identification of an Unknown
Identity number of my unknown:
Approximate melting point range:
Experiment 1 Report Sheet
Accurate melting point range:
Melting point mixed with , °C
Melting point mixed with , °C
My unknown compound is .
Questions
1. Why is it essential to (a) pack the sample tightly in the melting point tube and (b) heat the sample slowly
and steadily as the melting point temperature is approached?
2. What is the effect of using too large a sample when determining a melting point?
3. Research chemists when determining the melting points of newly synthesized compounds often fill a
second capillary tube with a known substance (of similar melting point range) and co-determine the
melting points of the two substances using the same apparatus. What purpose does the determination of the
melting point of the known substance serve?
4. For what two purposes are melting points routinely used?
a.
b.
5. Three test tubes contain white crystalline organic solids A, B and C, each of which melts at 149–150°C. A
50–50 mixture of A and B melts at 130–139°C. A 50–50 mixture of A and C melts at 149–150°C. In what
range would a 50–50 mixture of B and C probably melt?
What can you say about the identities of A, B and C?
10
EXPERIMENT
2 Recrystallization:
Purification of Crystalline
Organic Compounds
Impure crystalline substances can be purified by recrystallization from a suitable solvent. This
process depends on two facts: Most compounds are more soluble in hot solvents than in cold
ones, and impurities have solubilities different from those of the desired compound. The
procedure involves (1) dissolving the impure material in a minimum amount of boiling solvent,
(2) filtering the hot solution to remove insoluble impurities, (3) allowing the solution to cool
slowly to deposit crystals of the compound, (4) filtering the crystals from the solution (called the
mother liquor), (5) washing the crystals with a little cold solvent to remove the mother liquor,
and (6) drying the crystals to remove the last traces of solvent.
This experiment illustrates recrystallization (a) from a single solvent (water) and (b) from a
mixed solvent (ethanol-water).
1 General Principles
If recrystallization is to be effective, the solvent must be properly selected. A good
recrystallization solvent should (1) dissolve a moderate quantity of the substance being purified
at an elevated temperature, but only a small quantity at low temperature, (2) not react with the
substance being purified, (3) dissolve impurities readily at a low temperature or not dissolve
them at all, and (4) be readily removable from the purified product. This last requirement
usually means that the solvent should have a fairly low boiling point and evaporate readily. If a
single solvent cannot be found that meets all these requirements, a mixture of two solvents may
be used.
Solvents suitable for recrystallizing a known compound are usually reported in the chemical
literature. If none is reported, or if the substance is a new compound, several solvents can be
tested in the following way. Place about 10 mg (a small spatula tipful) of the substance to be
purified in each of several small test tubes, and add about 0.25 mL of a different solvent to each.
Then observe the solubility of the sample in each solvent, when cold and when heated. Also
note whether abundant, well-formed crystals are produced as the hot solution cools.
Caution Since many recrystallization solvents are flammable, do not use Bunsen burners to heat solutions
unless your instructor indicates that you should do so. If you must use an open flame to heat a
flammable solvent, follow your instructor’s directions closely.
11
12 Experiment 2 Recrystallization: Purification of Crystalline Organic Compounds
stirring rod to guide

liquid into funnel
cloth or paper to
protect hand against
fluted paper heat from solution
in funnel
“short” - stemmed funnel
Figure 2.1 Filtration of a

hot solution using fluted
filter paper.
To obtain a good recovery of purified material, it is best to avoid using unnecessarily

large volumes of solvent. Dissolving the substance in the smallest possible amount of hot
solvent minimizes the amount of material lost by retention in the mother liquors. In practice,
3–5% more solvent than the minimum required is used so that the hot solution will be not
quite saturated. This helps to prevent separation of the crystals and clogging of the filter
paper during filtration of the hot solution.
Traces of coloring matter or resinous impurities can sometimes be removed with
selective adsorbents, such as finely divided charcoal (Norit, Darco). To do this, add a small
amount of decolorizing charcoal to the warm* solution before filtering it. Avoid using excess
decolorizing agent, however, because it may also adsorb appreciable amounts of the
substance being purified.
Some substances readily form supersaturated solutions, and crystallization may not
occur spontaneously when the hot solution is cooled. In such situations, it is sometimes
possible to initiate crystallization by scratching the walls of the vessel beneath the surface of
the solution with a stirring rod. Though the effect of scratching the inside walls of the vessel
in inducing crystallization is not well understood, two possible explanation are: (a) the fine
glass particles produced through such scratching may act as nuclei on which crystallization
may begin, or more likely, (b) small amounts of the solution drawn onto the sides of the
vessel during scratching evaporate to produce dry solutes that are pushed back into the
solution. These finely divided solute particles act as nuclei for crystallization to start. The
best way to induce crystallization is to “seed” the cold solution with one or two crystals of
the substance being purified. Although some compounds crystallize readily, others may
separate from solution as oils, and it may take some time before they crystallize.
2 Apparatus for Hot Filtration and Vacuum Filtration
To remove insoluble impurities and decolorizing charcoal, it is necessary to filter the solution
while it is hot. Otherwise, when the solution cools, crystals deposit prematurely. Rapid
filtration can be accomplished by using fluted filter paper (paper folded with many pleats to
give a large surface, Figure 2.1) or by using a vacuum to increase the filtration rate. Vacuum
*Do not add decolorizing charcoal to a hot solution. If a solution is at or near its boiling point, the
addition of finely divided charcoal (which acts as thousands of boiling chips) will cause rapid boil over.
Experiment 2 Recrystallization: Purification of Crystalline Organic Compounds 13
Büchner funnel (or Hirsch funnel)
stopcock for release

of vacuum
to water
aspirator
(vacuum) Figure 2.2 Apparatus for
filter flask
vacuum filtration.
water trap
filtration is generally used to remove soluble impurities and solvent from the crystals of the
purified substance. Figure 2.2 shows the apparatus for vacuum filtration. A Büchner or a
Hirsch funnel is fitted to a filter flask with a tight-fitting rubber stopper. A disc of filter paper
just large enough to cover all the holes in the funnel is placed in the funnel and moistened
with some of the solvent used in the recrystallization. The filter flask is then connected to the
aspirator by thick-walled rubber tubing through a water trap, and vacuum is applied. When
the filter paper is drawn tightly to the funnel, the solution and crystals are transferred to the
funnel. The solution passes through the paper, while the crystals deposit on the paper.
3 Reflux Apparatus
It is sometimes necessary to heat a substance in a solvent for a long time without boiling
away the solvent. This can be done by attaching a vertical condenser to the flask containing
the boiling solution (Figure 2.3). The solvent vapor, upon cooling, condenses and returns as a
liquid to the boiling solution. This process of continuous boiling, vaporization, cooling, and
return of condensate is called refluxing. In recrystallizing, it is sometimes necessary to use a
reflux apparatus to obtain a solution of the material to be purified because the dissolution
process may be slow. We also use the reflux technique when recrystallizing large samples
from volatile, flammable solvents (a sand, steam, or oil bath or an electric mantle is
employed as the source of heat).
Another random document with
no related content on Scribd:
CHAPTER VI.
REPTON’S MERRY BELLS.
“Barrow’s big boulders, Repton’s merry bells,

Foremark’s cracked pancheons, and Newton’s egg shells.”
Thus does a local poet compare Repton bells with those of

neighbouring parishes. It is not intended to defend the comparison,
for as Dogberry says, “Comparisons are odorous”! but to write an
account of the bells, derived from all sources, ancient and modern.
Llewellynn Jewitt, in Vol. XIII. of the Reliquary, describing the bells
of Repton, writes, “at the church in the time of Edward VI. there were
iij great bells & ij small.” Unfortunately “the Churchwardens’ and
Constables’ accounts of the Parish of Repton” only extend from the
year 1582 to 1635. I have copied out most of the references to our
bells entered in them, which will, I hope, be interesting to my
readers.
Extracts from “the Churchwardens’ and Constables’ accounts of the
Parish of Repton.”
A.D. 1583. The levy for the bell vjˡⁱ ixˢ 0

It’ spent at takying downe the bell xvjᵈ
It’ payd to the Bellfounder xxxiijˢ iijᵈ
It’ bestowed on the s’vants at casting
of ye bell xvjᵈ
It’ expensys drawing up the bell vijᵈ
It’ to the ryngers the xviiᵗʰ day of
november xijᵈ
A.D. 1584. Recevyd of the levy for the bell vjˡⁱ xˢ vijᵈ
It’ of Bretby towards the bell vjˢ viijᵈ
It’ spent at taking downe ye bell viijᵈ
It’ bestowed on the bell founder ijᵈ
It’ Payd to Bellfounder for weight, i.e.,
iiij score & ij pounds iijˡⁱ xiˢ viijᵈ
A.D. 1585. It’ for a bell rope for the great bell ijˢ
It’ to John Pratt for makinge iiij newe
bellropes vˢ
It’ the day before Saynt Hew’s day for
mendyng the bels, & for nayles viijᵈ
A.D. 1586. It’ of our ladie’s even, given to the
ringers for the preservation of
our Queene xijᵈ
Our ladie’s even, eve of the
Annunciation of the Blessed
Virgin Mary (March 25th).
Preservation of our Queene Elizabeth
from the Babington Conspiracy.
A.D. 1587. It’ given unto the ringers uppon
coronation daye iijᵈ
A.D. 1589. It’ for a bell rope ijˢ viijᵈ
A.D. 1590. It’ payde to francis Eaton for
mendynge the irons aboutt the
bells ijˢ iijᵈ
A.D. 1592. It’ payde to Ralphe Weanwryghte for
trussynge the bells agyne the
Coronacyon daye iijˢ
A.D. 1600. It’ spent in takinge downe ye beell xijᵈ
It’ payd to John Welsh fordowne
takinge hitt donne vjᵈ
It’ spent in lodinge hitt iiijᵈ
It’ spent in charges going with the
beell to Nottingham, being towe
days and one night vjˢ viijᵈ
It’ payd to ye bellfounder for castinge
ye beell iiijˡⁱ xviijˢ
It’ spent with him ijᵈ
It’ payd for yookeinge ye Beell and ijˢ viijᵈ
for greysse
It’ spent uppon them that holpe with
the beell xᵈ
A.D. 1603. It’ given to the ringers uppon New
yeares daye morninge vjᵈ
It’ given to ye ringers upon St. James
daye (July 25th) xijᵈ
It’ given to ye ringers the v daye of
August xijᵈ
A.D. 1605. It’ payd at hanginge up ye greatte bell vjᵈ
It’ bestowed of ye Ringers at ye first
Ringinge of ye bells vijᵈ
It’ payd for greese for ye bells viijᵈ
A.D. 1607. It’ given to ye Ringers uppon
Christmas daye morning iiijᵈ
A.D. 1614. It’ towe bellclappers
A.D. 1615. The names of them that gave money
to bye the newe beell 80
(Repton, 62. Milton, 18.)
Sum gathered xijˡⁱ viijˢ viijᵈ
A.D. 1623. First paide for castinge the bell vˡⁱ
It’ given to the Ringers at the time of
Prince Charlles his comminge
forth of spaine. (Oct. 1623). xijᵈ
Extract from the diary of Mr. George Gilbert.
“A.D. 1772, Oct. 7th. The third bell was cracked, upon ringing
at Mr. John Thorpe’s wedding. The bell upon being taken
down, weighed 7 cwt. 2 qr. 18lb., clapper, 24lb. It was
sold at 10d. per lb., £35. 18s. Re-hung the third bell, Nov.
21st, 1774. Weight 8 cwt. 3 qr. 24lb., at 13d. per lb., £54.
7s. 8d., clapper, 1 r. 22 lb., at 22d., £1. 2s. 10d. £55. 9s
6½d.”
This is all the information I can gather about “Repton’s merry bells”
from ancient sources.
For some time our ring of six bells had only been “chimed,” owing
to the state of the beams which supported them, it was considered
dangerous to “ring” them.
During the month of January, 1896, Messrs. John Taylor and Co.,
of Loughborough, (descendants of a long line of bell-founders),
lowered the bells down, and conveyed them to Loughborough,
where they were thoroughly cleansed and examined. Four of them
were sound, but two, the 5th and 6th, were found to be cracked, the
6th (the Tenor bell) worse than the 5th. The crack started in both
bells from the “crown staple,” from which the “clapper” hangs; it (the
staple) is made of iron and cast into the crown of the bell. This has
been the cause of many cracked bells. The two metals, bell-metal
and iron, not yielding equally, one has to give way, and this is
generally the bell metal. The “Canons,” as the projecting pieces of
metal forming the handle, and cast with the bell, are called, and by
which they are fastened to the “headstocks,” or axle tree, were found
to be much worn with age. All the “Canons” have been removed,
holes have been drilled through the crown, the staples removed, and
new ones have been made which pass through the centre hole, and
upwards through a square hole in the headstocks, made of iron, to
replace the old wooden ones. New bell-frames of iron, made in the
shape of the letter H, fixed into oak beams above and below, support
the bells, which are now raised about three feet above the bell
chamber floor, and thus they can be examined more easily.
During the restoration of the Church in 1886, the opening of the
west arch necessitated the removal of the ringers’ chamber floor,
which had been made, at some period or other, between the ground
floor and the groined roof, so the ringers had to mount above the
groined ceiling when they had to ring or chime the bells. There,
owing to want of distance between them and the bells, the labour
and inconvenience of ringing was doubled, the want of sufficient
leverage was much felt: now the ringers stand on the ground floor,
and with new ropes and new “sally-guides” their labour is lessened,
and the ringing improved.
When the bells were brought back from Loughboro’ I made careful
“rubbings” of the inscriptions, legends, bell-marks, &c., before they
were raised and fixed in the belfry. The information thus obtained,
together with that in Vol. XIII. of the Reliquary, has enabled me to
publish the following details about the bells.
The “rubbings” and “squeezes” for the article in the Reliquary were
obtained by W. M. Conway (now Sir Martin Conway) when he was a
boy at Repton School.
Plate 6.
REPTON BELL MARKS AND ORNAMENTS.
The 1st (treble) Bell.

On the haunch, between three lines, one above, two below,
FRAVNCIS THACKER OF LINCOLNS INN ESQᴿ, 1721.
a border: fleurs-de-lis (fig. 7): Bell-mark of Abraham Rudhall, (a

famous bell-founder of Gloucester): border (fig. 7).
A catalogue of Rings of Bells cast by A. R. and others, from 1684-
1830, is in the Bodleian Library, Oxford: this bell is mentioned as the
gift of Francis Thacker.
At the east end of the north aisle of our Church there is a mural
monument to his memory.
The 2nd Bell.
On the crown a border of fleurs-de-lis (fig. 9). Round the haunch,
Is sweetly toling men do call to taste on meats that feed the soule
between two lines above and below, then below the same border
(fig. 9) inverted.
1622 Godfrey Thacker Iane Thacker
This bell is referred to in the Churchwardens’ accounts under

dates 1615 and 1623.
The 3rd Bell.
Round the haunch, between two lines,
THOˢ. GILBERT & IOHN TETLEY CHVRCH WARDENS 1774 PACK & CHAPMAN
OF LONDON FECIT
Below, a border, semicircles intertwined.

This is the bell referred to in the extract quoted above from George
Gilbert’s diary.
The 4th Bell.
Round the haunch, between six lines (3 above and 3 below),
✠ Melodie Nomen Tenet Magdelene
a shield: three bells (two and one), with a crown between them (fig.
1), (Bell mark of Richard Brasyer, a celebrated Norwich Bell founder,
who died in 1513) a lion’s head on a square (fig. 2): a crown on a
square (fig. 3); and a cross (fig. 5).
The 5th Bell.
Round the haunch, between two lines, one above, one below,
✠ Vox du̅ i̅ ihū x̅ r̅ i̅ vox exultarionis
same marks (except the crown) as No. 4 Bell: a king’s head crowned
(fig. 4): and a cross (fig. 6). Below this, round the haunch, a beautiful
border composed of a bunch of grapes and a vine leaf (fig. 8),
alternately arranged.
Below, the Bell mark of John Taylor and Co. within a double circle,
a triangle interlaced with a trefoil, and a bell in the centre. Above the
circle the sacred emblem of S. John Baptist, the lamb, cross, and
flag. The name of the firm within the circle.
RECAST 1896.
The 6th Bell (the tenor Bell).
Round the haunch, between four lines, two above, and two below,
Hec Campana Sacra Fiat Trinitate Beata GILB THACKAR ESQ IC MW CH

WARDENS 1677
(no bell marks).

Below, a border like that on the fifth Bell.
RECAST 1896.
G. WOODYATT, VICAR.
J. ASTLE, }
CHURCHWARDENS.
T. E. AUDEN, }
Bell mark of J. Taylor and Co. on the opposite side.

(Owing to the difference of the type of the inscription, and names,
it is supposed that this bell was recast in 1677, so it may have been
one of the “three great bells” in Edward VI.’s time.)
The following particulars of the bells have been supplied by
Messrs. John Taylor & Co.
Diameter. Height. Note. Weight.

ft. in. ft. in. cwt. qr. lbs.
No. I. 2 9½ 2 3 C♯ 7 3 19
” II. 2 10¾ 2 4½ B 7 2 27
” III. 3 0½ 2 4½ A 8 1 18
” IV. 3 2 2 6½ G♯ 9 2 21
” V. 3 6 2 10 F♯ 12 2 26
” VI. 3 11 3 1 E 17 3 0
Total 3 tons 4 cwts. 0 qrs. 27 lbs.
Key-note E major.
To complete the octave, two more bells are required, D ♯ and E,
then indeed Repton will have a “ring” second to none.
CHAPTER VII.
THE PRIORY.
THE PRIORY FOUNDED, &c.

Before we write an account of the next most important event in the
history of Repton, viz., the founding of Repton Priory, we must go
back to the year 1059, when Calke Abbey is supposed to have been
founded by Algar, Earl of Mercia. Dr. Cox is of opinion that it was
founded later, at the end of the reign of William (Rufus), or at the
beginning of that of Henry I. circa 1100. About that date a Priory of
Canons regular of St. Augustine, dedicated to St. Giles, was
founded. Many benefactors made grants of churches, lands, &c., a
list of all these will be found in Cox’s Derbyshire Churches, vol. iii., p.
346. There is a curious old Chronicle, written in Latin, by one
T(h)omas de Musca, Canon of Dale Abbey. Each section of the
Chronicle begins with a letter which, together, form the Author’s
name, a monkish custom not uncommon. The section beginning with
an E. (Eo tempore) records the arrival, at Deepdale, of the Black
Canons, as they were called, from Kalc (Calke). Serlo de Grendon,
Lord of Badeley or Bradeley, near Ashbourne, “called together the
Canons of Kalc, and gave them the place of Deepdale.” Here, about
1160, the Canons “built for themselves a church, a costly labour, and
other offices,” which became known as Dale Abbey, in which they
lived for a time, “apart from the social intercourse of men,” but “they
began too remissly to hold themselves in the service of God; they
began to frequent the forest more than the church; more to hunting
than to prayer or meditation, so the King ordered them to return to
the place whence they came,” viz., Calke. During the reign of Henry
II., Matilda, widow of Randulf, 4th Earl of Chester, who died 1153,
granted to God, St. Mary, the Holy Trinity, and to the Canons of
Calke, the working of a quarry at Repton, (Repton Rocks), together
with the advowson of the church of St. Wystan at Repton, &c., &c.,
on condition that as soon as a suitable opportunity should occur, the
Canons of Calke should remove to Repton, which was to be their
chief house, and Calke Abbey was to become subject to it. “A
suitable opportunity occurred” during the episcopate of Walter
Durdent, Bishop of Coventry only, at first, afterwards of Lichfield. He
died at Rome, Dec. 7th, 1159. The usual date given for the founding
of Repton Priory is a.d. 1172, but this must be wrong for the simple
reason that Matilda addresses the Charter of Foundation to Bishop
Walter Durdent, who died, as we saw, in 1159: moreover, the
“remains” of the Priory belong to an earlier date; probably the date
1172 refers to the coming of the Canons from Calke to Repton, as
Dugdale writes, “About the year 1172, Maud, widow of Randulf,
removed the greater part of them here (Repton), having prepared a
church and conventual buildings for their reception.” To those
interested in Charters, copies of the original, and many others, can
be read in Bigsby’s “History of Repton,” Dugdale’s “Monasticon,” and
Stebbing-Shaw’s Article in Vol. II. of “the Topographer,” in which he
has copied several “original Charters, not printed in the Monasticon,”
which were in the possession of Sir Robert Burdett, Bart., of
Foremark, and others.
Plate 7.
Repton Priory.
The Charters, containing grants, extend from Stephen’s reign,

(1135-1154), to the reign of Henry V., (1413-1422), and include the
church of St. Wystan, Repton, with its chapels of Newton Solney,
Bretby, Milton, Foremark, Ingleby, Tickenhall, Smisby, and Measham,
the church at Badow, in Essex, estates at Willington, including its
church, and Croxall.
In 1278 a dispute arose between the Prior of Repton and the
inhabitants of the Chapelry of Measham, which had been granted to
the Priory about 1271. The chancel of Measham Church was “out of
repair,” and the question was, who should repair it? After
considerable debate, it was settled that the inhabitants would re-
build the chancel provided that the Priory should find a priest to
officiate in the church, and should keep the chancel in repair for ever
after, both of which they did till the dissolution of the Priory.
In the year 1364 Robert de Stretton, Bishop of Lichfield (1360-
1386), was holding a visitation at Repton in the Chapter House of the
Priory. For some reason or other, not known, the villagers, armed
with bows and arrows, swords and cudgels, with much tumult, made
an assault on the Priory gate-house. The Bishop sent for Sir Alured
de Solney, and Sir Robert Francis, Lords of the Manors of Newton
Solney and Foremark, who came, and quickly quelled this early
“town and gown” row, without any actual breach of the peace. The
monument in the crypt of Repton Church, where it was placed during
the “restoration” of 1792, is supposed to be an effigy of Sir Robert
Frances. “The Bishop proceeded on his journey, and, on reaching
Alfreton, issued a sentence of interdict on the town and Parish
Church of Repton, with a command to the clergy, in the neighbouring
churches, to publish the same under pain of greater
excommunication.” See Lichfield Diocesan Registers.
On October 26th, 1503, during the reign of Henry VII., an
inquisition was held at Newark. A complaint was heard against the
Prior of Repton for not providing a priest “to sing” the service in a
chapel on Swarkeston Bridge, “nor had one been provided for the
space of twenty years, although a piece of land between the bridge
and Ingleby, of the annual value of six marks, had been given to the
Prior for that purpose.”
THE PRIORY DISSOLVED AND DESTROYED.

The Priory of Repton was dissolved in the year 1538. By the
advice of Thomas Cromwell—malleus monachorum—the hammer of
the monks—Henry VIII. issued a commission of inquiry into the
condition, &c., of the monasteries in England. A visitation was made
in 1535, the results were laid before the House of Commons, in a
report commonly known as the “Black Book.” In 1536 an Act was
passed for the suppression of all monasteries possessing an income
of less than £200. a year. By this Act 376 monasteries were
dissolved, and their revenues, £32,000. per annum, were granted to
the King, by Divine permission Head of the Church! Repton Priory
was among them. In the Valor Ecclesiasticus (27 Henry VIII.) the
gross annual value of the temporalities and spiritualities is given as
£167. 18s. 2½d. In 1535, Dr. Thomas Leigh and Dr. Richard Layton,
visited Repton and gave the amount as £180. Also they reported, as
they were expected, that the Canons were not living up to their vows,
&c., &c., and “Thomas Thacker was put in possession of the scite of
the seid priory and all the demaynes to yᵗ apperteynying to oʳ
sov’aigne lorde the Kynges use the xxvj day of October in the xxx
yere of oʳ seid sov’aigne lorde Kyng henry the viijᵗʰ.” There is a very
full inventory of the goods and possessions in the Public Record
Office, Augmentation Office Book, 172. A transcript of this inventory
is given by Bigsby in his History of Repton, also by W. H. St. John
Hope, in Vol. VI. of the Derbyshire Archæological Journal. From this
inventory, and Mr. St. John Hope’s articles in the journal, a very good
account and description can be given of the Priory as it was at the
time of its dissolution.
The dissolved Priory was granted to Thomas Thacker in 1539, he
died in 1548, leaving his property to his son Gilbert. He, according to
Fuller (Church History, bk. vi., p. 358), “being alarmed with the news
that Queen Mary had set up abbeys again (and fearing how large a
reach such a precedent might have), upon a Sunday (belike the
better day, the better deed) called together the carpenters and
masons of that county, and plucked down in one day (churchwork is
a cripple in going up, but rides post in coming down) a most beautiful
church belonging thereto, saying “he would destroy the nest, for fear
the birds should build therein again”.” The destruction took place in
the year 1553. How well he accomplished the work is proved by the
ruins uncovered during the years 1883-4.
This Gilbert died in 1563, as set forth on the mural tablet in the
south aisle of Repton Church, a copy of which I have made, so that
my readers may see what sort of a person he was who “wrought
such a deed of shame.” Gilbert sold the remains of the Priory to the
executors of Sir John Port in 1557, he and his descendants lived at
the Hall till the year 1728, when Mary Thacker, heiress of the Manor
of Repton Priory, left it, and other estates, to Sir Robert Burdett, of
Foremark, Bart. Since that time the Hall has been occupied by the
Headmasters of Repton School.
REPTON PRIORY DESCRIBED.
The Priory followed the usual plan of monastic buildings, differing
chiefly in having the cloister on the north of its church, instead of the
south. This alteration was necessary owing to the river Trent being
on the north. In choosing a site for monasteries the water supply was
of the first consideration, as everything, domestic and sanitary,
depended on that. The Conventual buildings consisted of Gate-
house, Cloister, with Church on its south side, Refectory or Fratry on
its north. The Chapter Rouse, Calefactorium, with Dormitory above
them, on its east side. Kitchens, buttery, cellars, with Guest Hall over
them, on its west side. The Infirmary, now Repton Hall, “beside the
still waters” of the Trent, on the north of the Priory. The Priory
precincts, (now the Cricket ground), were surrounded by the existing
wall on the west, south, and east sides; on the north flowed, what is
now called, “the Old Trent,” and formed a boundary in that direction.
Plate 8.
Sir John Porte Knt. The Founder of Repton School. (F. C. H.) (Page 62.)
Gilbert Thacker. (Page 54.)
On the east side of the Priory was the Mill. The wall, with arch-
way, through which the water made its way across the grounds in a
north-westerly direction, is still in situ in the south-east corner of the
Cricket ground. The Priory, and well-stocked fish ponds, were thus
supplied with water for domestic, sanitary, and other purposes.
The bed of the stream was diverted to its present course, outside
the eastern boundary wall, by Sir John Harpur, in the year 1606.
The Gate-house (now represented by the School Arch, which was
its outer arch, and wall) consisted of a square building with an upper
chamber, and other rooms on the ground floor for the use of the
porter. Two “greate gates,” with a wicket door let into one of them, for
use when the gates were closed, or only pedestrians sought for
admission, provided an entrance to the Priory. Proceeding through
the arch-way of the Gate-house, we find ourselves in the precincts.
In the distance, on our left hand, was the Parish Church of St.
Wystan, on our right the Priory Church and conventual buildings.
The Priory Church consisted of nave, with north and south aisles,
central tower, north and south transepts, choir, with aisles, and a
south chapel, and a presbytery to the east of the choir. The Nave (95
ft. 6 in. long, and, with aisles, 51 ft. 8 in. wide) “was separated from
the aisles by an arcade of six arches, supported by clustered pillars
of good design, and must have been one of the most beautiful in this
part of the country, all of exceptionally good character and design,
and pertained to the transitional period of architecture which
prevailed during the reign of Edward I., (1272-1307), when the
severe simplicity of the Early English was merging into the more
flowing lines of the Decorated.” In the north aisle the foundations of
an older church, perhaps the original one, were discovered in 1883-
4.
There were several Chapels in the Nave, two of which are named,
viz., “Oʳ lady of petys Chapell” and the “Chapell of Saint Thomas,”
with images, “reredoses, of wood gylte, and alebaster,” “and a
partition of tymber seled ouerin seint Thom’s Chapell.” “vij. peces of
tymber and lytell oulde house of tymber,” probably the remains of a
shrine, and “xij. Apostells,” i.e. images of them. “j sacrying bell,”
sanctus bell, used during the celebration of the mass. In the floor, in
front of the central tower arch, a slab was discovered, (6 ft. 4 in. by 3
ft. 2 in.), bearing a rudely cut cross, with two steps, and an
inscription, in Old English letters, partly obliterated, round the margin
“(Orate pro) anima magistri edmundi duttoni quondam canonici huius
ecclisie qui obiit ... januarii anno diu mcccclᵒ cui’ ppic (deus Amen).”
This slab is now lying among the ruins at the east end of the Pears
School.
Central Tower (25 ft. by 21 ft. 6 in.) supported by four large piers.
Between the two eastern piers there was a pulpitum, a solid stone
screen (5 ft. 4½ in. deep), with a door in the centre (4 ft. 4½ in.
wide). In the northern half was a straight stone stair leading to the
organ loft above, where was “j ould pair of Organs,” a phrase often
met with in old inventories, and church accounts, in describing that
instrument of music. Through the passage under the screen we
enter the Choir. The step leading down to the choir floor, much worn
by the feet of the canons and pilgrims, is still in situ. The Choir (26 ft.
wide, 31 ft. long) was separated from the south Choir aisle, by an
arcade of five arches, from the north choir aisle, by an arcade of
three arches. All traces of the Canons’ stalls have gone, but there
was room for about thirty-four, thirteen on each side, and four
returned at the west end of the Choir. In the Choir was the High Altar
with “v. great Images” at the back of which was a retable, or ledge of
alabaster, with little images, (on a reredos with elaborate canopies
above them). “iiij lytle candlestyks” and “a laumpe of latten,” i.e., a
metal chiefly composed of copper, much used in church vessels,
also “j rode” or cross.
On the south of the choir was a chapel dedicated to St. John, with
his image, and alabaster table, similar to that in the choir. To the
south of St. John’s Chapel was the “Chapel our Lady” similarly
ornamented, these two chapels were separated from the south
transept by “partitions of tymber,” or screens, the holes in which the
screens were fixed are still to be seen in the bases of the pillars. On
the east of the choir was the Presbytery. In the South Transept was
the Chapel of St. Nicholas with images of St. John and St. Syth, (St.
Osyth, daughter of Frithwald, over-lord of the kingdom of Surrey, and
Wilterberga daughter of King Penda). Of the North Choir Aisle
nothing remains: it is supposed that in it was the shrine of St.
Guthlac, whose sanctus bell is thus referred to by the visitors in their
report “superstitio—Huc fit peregrinatio ad Sanctum Guthlacum et ad
eius campanam quam solent capitibus imponere ad restinguendum
dolorem capitis.” “Superstition. Hither a pilgrimage is made to (the
shrine of) St. Guthlac and his (sanctus) bell, which they were
accustomed to place to their heads for the cure of headache.” The
North Transept was separated from the north choir aisle by an
arcade of three arches, immediately to the east of which the
foundations of a wall, about six feet wide, were discovered, which,
like those in the north nave aisle, belonged to an older building.
Many beautiful, painted canopies, tabernacle work, &c., were found
among the débris of the north transept and aisle, which no doubt
adorned the shrines, and other similar erections, which, before the
suppression of the monasteries, had been destroyed, and their relics
taken away—that is, probably, the reason why we find no mention of
the shrines of St. Guthlac, or St. Wystan in the Inventory.
In the western wall of the North Transept there was a curious
recess (13 ft. 10 in. by 4 ft. 10 in.) which may have been the
armarium, or cupboard of the Vestry, to hold the various ornaments,
and vestments used by the Canons, “j Crosse of Coper, too tynacles,
(tunicles), ij albes, ij copes of velvet, j cope of Reysed Velvet, iiij
towels & iiij alter clothes, ij payented Alterclothes,” &c., &c.
Leaving the Church, we enter the Cloister, through the door at the
east end of the Nave, it opened into the south side of the Cloister (97
ft. 9 in. long by 95 ft. wide). Here were “seats,” and “a lavatory of
lead,” but, owing to alterations, very little indeed is left except the
outside walls. Passing along the eastern side we come to the
Chapter House, the base of its entrance, divided by a stone mullion
into two parts, was discovered, adjoining it on the north side was a
slype, or passage, through which the bodies of the Canons were
carried for interment in the cemetery outside. The slype (11¾ ft. wide
by 25½ ft. long) still retains its roof, “a plain barrel vault without ribs,
springing from a chamfered string course.” Next to the slype was the
Calefactorium or warming room. Over the Chapter House, Slype,
and Calefactorium was the Dormitory or Dorter, which was
composed of cells or cubicles.
The Fratry or Refectory occupied the north side of the Cloister,
here the Canons met for meals, which were eaten in silence,
excepting the voice of the reader. A pulpit was generally built on one
of the side walls, from which legends, &c., were read. Underneath
the Fratry was a passage, leading to the Infirmary, and rooms, used
for various purposes, Scriptorium, &c. At the east end of the Fratry
was the Necessarium, well built, well ventilated, and well flushed by
the water from the Mill race.
At the west end of the Fratry was the Buttery. The west side of the
Cloister was occupied by the Prior’s Chamber, and five others called,
in the Inventory, “the Inner,” “Gardyn,” “Next,” “Halle,” and “Hygh
Chambers.” All were furnished with “fether bedds, &c., &c.,” for the
use of guests, who were received and entertained in this part of the
Priory. Underneath these rooms were “the Kychenn,” “Larder,”
“Bruhouse,” &c., called the Cellarium, over which the Cellarer had
supreme authority. Originally the Cellarium was divided into three
parts, Kitchen, Cellar, and Slype or passage into the south side of
the Cloister. The part assigned to the Kitchen was sub-divided into
three rooms, one on the east side, two on the west. One of these two
(the south) has a vaulted roof, with plain square ribs, the boss where
they meet has been carved, and a part of one of the ribs has been
ornamented with the dog tooth moulding, for about 18 inches, there it
stopped unfinished, in the walls are many recesses for the reception
of “plate,” &c.
The Cellar was a long room (89 ft. by 26 ft.), divided into two
“alleys” by a row of six massive Norman columns, four of which
remain, one has a scollopped capital, the others are plain. The floor
above was divided in a similar manner, with the Prior’s Chamber at
the north end, the Guest Hall, divided into the various rooms
mentioned above, and a chamber over the slype, which was
probably used as a parlour by the guests.

PDF Lab Manual For Organic Chemistry A Short Course 13Th 13Th Edition David J Hart Ebook Full Chapter

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

PDF Lab Manual For Organic Chemistry A Short Course 13Th 13Th Edition David J Hart Ebook Full Chapter

Uploaded by

Copyright:

Available Formats

Lab Manual for Organic Chemistry A

Short Course 13th 13th Edition David J.

Study Guide and Solutions Manual Intl Edition for Hart

Organic Chemistry I Lab Manual 18th Edition David

Chemistry 13th Edition Raymond Chang

Organic Chemistry 2nd Edition Robert J. Ouellette And

Choices in Relationships 13th Edition David Knox

Financial Markets & Institutions (MindTap Course List)

Accounting Principles, 13th Edition Jerry J. Weygandt

Organic Chemistry Student Study Guide and Solutions

Publisher: Mary Finch

Cover image: © Steve Taylor/Getty Images

Printed in the United States of America

Introduction: To the Student viii

1. Melting Point Determination: Purity and Identity of Crystalline

2. Recrystallization: Purification of Crystalline Organic Compounds 11

3. Distillation: Separation and Purification of Organic Liquids 23

4. Extraction: A Separation and Isolation Technique 33

5. Isolation of Natural Products: Caffeine and Eugenol 47

Chemistry at Home: Spice Essences 57

6. Chromatography: Column, Thin-Layer, Gas-Liquid, and Paper 59

Chemistry at Home: Food Dyes and Marking Pens 77

7. Conformations of Alkanes and Cycloalkanes: An Exercise with Molecular Models and

8. Preparation of Alkenes from Cyclohexanol or 2-Methyl-2-butanol, and Tests for

9. Cis-Trans Isomerism in Alkenes: Models and Experiments 123

10. Cycloadditions: The Diels-Alder Reaction 133

11. Electrophilic Aromatic Substitution 149

12. Stereoisomerism: Principles Illustrated with Molecular

13. Alkyl Halides: Structure and Reactivity in Nucleophilic Substitutions 199

14. The Hydroxyl Group: Reactions of Alcohols and Phenols 215

15. Reactions of Aldehydes and Ketones 231

16. Oxidation of Alcohols and Reduction of Ketones 253

17. Oxidation of Aldehydes to Carboxylic Acids: A Green Chemistry Experiment 265

18. Two Ways to Synthesize a Carboxylic Acid 271

19. Reactions of Carboxylic Acids and Their Derivatives 283

Chemistry at Home: Eggshells and Vinegar 301

20. Esters: Synthesis and Saponification of Methyl Benzoate 303

Chemistry at Home: Saponification Is Making Soap 315

21. Synthesis of Aspirin (Acetylsalicylic Acid) 319

22. Amines and Diazonium Compounds 327

23. Preparation of Sulfanilamide: A Multistep Synthesis 341

24. Dyes and Dyeing 351

Chemistry at Home: Natures’s Indicators and What They Indicate 366

25. Infrared and NMR Spectroscopy 369

26. Synthesis of a Heterocycle: 2-Amino-4,6-dimethylpyrimidine 379

28. Synthetic Polymers 395

29. Fats and Oils; Soaps and Detergents 409

Chemistry at Home: Soap and Talcum Powder 421

30. Reactions of Carbohydrates 423

Chemistry at Home: Where’s the Starch? 439

31. Amino Acids and Proteins 441

Chemistry at Home: Enzymes Are Nature’s Catalysts 461

Appendix A Some Useful Atomic Weights 463

Appendix C Concentrations of Common Reagents 463

Appendix D Preparation of Special Reagents 464

Appendix E Chemicals Required for Each Experiment 465

Appendix F Suggested Equipment for Each Student 481

The Thirteenth Edition

Microscale A large number of undergraduate teaching laboratories have converted to microscale

**Williamson, K. L., and Masters, K. M., Macroscale and Microscale Organic

Aims of Laboratory Work

General Laboratory Instructions and Pre-Lab Preparations

3. Locate the first aid kits.