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Liverpool John Moores University School of Pharmacy and Biomolecular Sciences

PHARMACEUTICAL CHEMISTRY PHCMC1022 MODULE HANDBOOK 2008 - 2009


Module Leader: Dr Ian J Bradshaw

PHARMACEUTICAL CHEMISTRY MODULE HANDBOOK 2007 - 2008

CONTENTS
1. Introduction 2. Conduct 3. Safety 4. Computer-Aided Learning 5. Subject Areas and Indicative References 6. Practical Classes 7. Timetable 8. Examinations

1. INTRODUCTION
This handbook has been prepared for your benefit and we believe it contains much useful information. We would welcome any critical feedback on the handbook and how it could be improved in the future. It is strongly recommended that you print a hard-copy of this document for future reference. Important information Module leader: Room: Telephone: e-mail: Dr Ian J Bradshaw Room 903 James Parsons Tower 0151 231 2014 i.j.bradshaw@ljmu.ac.uk

Pharmaceutical chemistry is a year-long twenty-four credit core module on the BSc (Hons) Applied Chemical and Pharmaceutical Sciences and Master of Pharmacy Degree programmes. Students with Disabilities Students are requested to identify any disabilities including dyslexia during the admissions process. This information is treated as strictly confidential but the University has to be informed, before learning support can be arranged for you. Following enrolment you should contact the Schools Disability Co-ordinator (Dr Bob Jones), who will act as internal (and, where appropriate, external) link in helping you to get the help you need and, with your permission, notify appropriate staff. It is important that you realise that by not declaring your disability you may not be able to receive practical help available to you and financial support such as the disabled students allowance. Purpose of Pharmaceutical Chemistry Module Chemistry is at the heart of drug action. The chemical properties of a drug determine how it needs to be delivered, how it is transported around the body, how it interacts with systems in the body and how it is removed from the body. The material in this module will build upon your existing chemical knowledge to help you understand how drugs behave both inside and outside the body. More specifically this module will provide you with an overview of aspects of chemistry and biochemistry that are significant with respect to the properties and analysis of drugs and their dosage forms. This overview will enable you to appreciate those chemical properties that are significant for biochemical transformation in vivo and the interaction of drugs with body chemistry. Such information is vital for an appreciation of drug action and the subtler functions of pharmacology. Further, on completion of this module, you should be familiar with a variety of analytical techniques available to the scientists in the pharmaceutical sciences and the reasons for their application.

Module mark

The pass mark for this module is 40%. The module mark is comprised 30% from coursework and 70% from the examination. Please refer to information on examinations later in this document. Under University Regulations no module marks will be released to students until they have been presented at the appropriate examination board. In terms of this module this may mean the end of the academic year. Key skills This course is designed to help you develop many key skills including the following: 1. 2. 3. 4. 5. 6. Perform analytical techniques within the laboratory Communicate scientific information in a competent manner Perform scientific calculations Interpret scientific data to enable you to reach a conclusion Retrieve scientific information from reference sources Develop the skills necessary to write reports

Staff In the School of Pharmacy and Chemistry we pride ourselves on the approachability of our staff and the good relations we maintain normally with the student population. If you have queries relating to this module please feel free to contact the appropriate member of staff. Please note that during certain busy periods we may not be able to answer your query directly but would be happy to arrange an appointment at a mutually convenient time. The main contributors to this module are: Prof. Mark Cronin Dr Chris Rostron Dr Fyaz Ismail Dr Linda Seton Dr Ian Bradshaw Dr Barry Nicholls Room 650 Room 909 Room 202a Room 221d Room 903 Room 202b

Module Assessment Schedule


Type of Assessment: Coursework Assignments: 9% of module mark Name of Coursework Assignment Type of Assessment Contribution to module mark 1.5% 1.5% 1.5% 1.5% 1.5% 1.5% Submission Details Assessment Criteria Marking Scheme Learning Outcomes Being Assessed (refer to Module Proforma) 3, 5 2, 8 1 1, 8 2, 7 2, 8, 9

Quantitative Analysis Organic Chemistry IUPAC Nomenclature Functional Group Chemistry Heterocyclic Chemistry Biologically Important Molecules

Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment

Date of assessment to be confirmed Date of assessment to be confirmed Date of assessment to be confirmed Date of Assessment to be confirmed Date of Assessment to be confirmed Date of Assessment to be confirmed

Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment Multiple Choice Assessment

N/A N/A N/A N/A N/A N/A

Type of Assessment: Practical Reports: 21% of module mark Type of Assessment Weighing, measuring, accuracy, precision, COSHH Standardisation of HCl titration Practical Report Prelaboratory work, Contribution to module mark 2.1% 1.05% Submission Details In practical class one week after practical taken Date to be arranged Assessment Criteria Quality of Practical Work and Comprehension of the Subject Area Quality of Practical Work and Comprehension of the Subject Area Marking Scheme Available on Blackboard Available on Blackboard 3, 5, 6 3, 5

Determination of acid titration

Standardisation of Potassium Permanganate titration

Calcium salt titration

Hydrogen Peroxide titration

ChemiCal exercise and marks for Accuracy and Precision of Titration Prelaboratory work, Practical Report and marks for accuracy and precision of titration Prelaboratory work, ChemiCal exercise and marks for Accuracy and Precision of Titration Prelaboratory work, ChemiCal exercise and marks for Accuracy and Precision of Titration Prelaboratory work,

1.05%

In practical class one week after practical taken

Quality of practical work and comprehension of subject area

Available on Blackboard

3, 5

0.7%

Date to be arranged

Quality of Practical Work and Comprehension of the Subject Area

Available on Blackboard

3, 5

0.7%

Date to be arranged

Quality of Practical Work and Comprehension of the Subject Area

Available on Blackboard

3, 5

0.7%

In practical class one week after practical taken

Quality of Practical Work and Comprehension of the Subject Area

Available on Blackboard

3, 5

Determination of pKa of 2-nitrophenol Investigation of unimolecular solvolysis Synthesis and analysis of aspirin

Practical Report and marks for Accuracy and Precision of Titration Practical Report Blackboard Multiple Choice Assessment Prelaboratory work, practical report To be confirmed Practical Report Prelaboratory work, ChemiCal exercise and marks for Accuracy and Precision of Titration Prelaboratory work, ChemiCal exercise and

2.1% 2.1%

In practical class one week after practical taken Assessment deadline to be confirmed In practical class one week after practical taken

Quality of Practical Work and Comprehension of the Subject Area Quality of Practical Work and Comprehension of the Subject Area Quality of practical work and comprehension of the subject area Quality of practical work and comprehension of the subject area Quality of Practical Work and Comprehension of the Subject Area Quality of Practical Work and Comprehension of the Subject Area

Available on Blackboard N/A

3, 4, 5, 10 8, 10

2.1%

Available on Blackboard

1, 2, 5

Carbohydrate Chemistry exercise Identification of an unknown drug sample Iodine titration

2.1% 2.1% 1.05%

In practical class one week after practical taken In practical class one week after practical taken Date to be confirmed

Available on Blackboard Available on Blackboard Available on Blackboard

1,5,9 1, 5, 9, 10 3, 5

Formol titration

1.05%

Date to be determined

Quality of Practical Work and Comprehension of the Subject Area

Available on Blackboard

3, 5

marks for Accuracy and Precision of Titration Type of Assignment: Examination Name of Coursework Assignment Type of Assessment Contribution to module mark 70% Submission Details Assessment Criteria Marking Scheme Learning Outcomes Being Assessed (refer to Module Proforma) 1-6, 8-11

3-hour examination

Examination

Date of exam to be confirmed by examination office

Comprehension of the Subject Area

N/A

2. CONDUCT
This module is subject to the Regulations of Liverpool John Moores University. Please note the following specific items: Attendance at lectures A lecture timetable will be issued. Please note any changes to this timetable which will be announced prior to the event. Check the Blackboard and emails daily for such information. A list of exact start times for lectures is published. Any variations on this will be announced. Lecturers will not normally allow late-comers admittance to the lecture room. Practical class and tutorial attendance Attendance at practical and tutorial sessions is compulsory and will be recorded. Late admission into practical classes is not permissible due to Health and Safety reasons. Lecture Handouts Occasionally lecturers may supply students with a handout to accompany the lecture information. These may reinforce the lecture material, give supplementary information, or may contain complex diagrams etc. These may be supplied after the lecture series and in no circumstances are they to be considered a substitute for good lecture notes. Handouts will be available normally only to those who attend lectures. Rather than you being given hard-copy of some handouts and other course information, they may be made available to you on the Liverpool John Moores University Blackboard System. You may, for example, find course information and notes appertaining to lecture material under the name of the lecturer. You will need a University username and password to access some of this material. More information will be supplied at the appropriate time. Assignments A number of assignments will be set during the module. The outcome of the assignments will provide you information on your academic progress through this module. For assignments in Semester 1 (and some assignments in Semester 2) you should prepare the answers by the set deadline. A convenient date will then be arranged for you to complete the assignment on EDPAC forms, to enable computer marking of the assignments. Please note the Dr Cronin/Dr Nichollss Chemical Analysis Assignment, and other assignments, will be available only on "Blackboard" on the University's networked computers. You will not be given a hard copy of these assignments. It is your responsibility to obtain this assignment from the network. Further details will be supplied at an appropriate time.

Plagiarism YOU WILL BE GIVEN MORE DETAILED INFORMATION REGARDING PLAGIARISM BY THE COURSE LEADER. IF YOU ARE IN ANY DOUBT AS TO WHAT CONSTITUTES PLAGIARISM, ASK A MEMBER OF ACADEMIC STAFF. Briefly, plagiarism is defined as the taking and using of anothers work as ones own. In this context you should assume that anothers work includes that of any student or member of staff, past or present, of Liverpool John Moores University, or any other source (such as text books, journal articles, internet etc.). Plagiarism applies to any aspect of the coursework, including, for example, practical work and reports, oral presentations, assignments and work for tutorial sessions. Please note that if reports are computer generated, these must be done individually by each student and for each piece of coursework. Plagiarism is an extremely serious offence and will be dealt with severely. You are referred to the regulations of the School of Pharmacy and Chemistry and Liverpool John Moores University for further information. Use and abuse of e-mail Electronic mail (e-mail) is an extremely useful and simple method of communication. It should not, however, be seen as an alternative to verbal communication. You should use email when it is not possible to contact a member of staff easily. It should be used to pass on important information, arrange meetings or inform members of staff of absences etc. Staff will also use e-mail to forward information to the class as a whole, or individuals within the class. If you are using e-mail please note the following guidelines: 1. Only send e-mails to those who need to receive them. It is time wasting and irritating to staff to receive e-mails that are not relevant. 2. Please put something meaningful in the Subject header (in a few words), so the person who receives it will have some idea of what the content. 3. DO NOT WRITE IN UPPER CASE. Unfortunately the University system makes you log on in upper case. Typing in upper case is the written equivalent of shouting. It is aggressive, difficult to read and unhelpful. 4. Please write in coherent English. There is always a temptation to write an e-mail in poorly constructed English, or not check the spelling. This does not assist the member of staff to comprehend and respond to your e-mail. 5. If you wish to arrange a meeting with the member of staff, please provide a number of options for specific times and dates so that the member of staff can reply efficiently to arrange a meeting. If you request a meeting via e-mail, please check your e-mail to see when it has been arranged for! 6. Please sign your e-mail with your full name, course and level.

3. SAFETY STATEMENT
Details on general laboratory safety will be supplied at the beginning of your course. Specific safety information regarding each individual practical class will be supplied. This is supplied normally at the start of a practical class. If you miss this information you are not able to participate in that practical session and thus you will be excluded if you arrive late for any class. Chemicals are potentially harmful - be careful.

4. COMPUTER-AIDED LEARNING
Computer-Aided Learning (CAL) forms a vital part of your learning experience in the School of Pharmacy and Chemistry. A number of packages are available to reinforce your key skills. Some indications of these, and their use in various parts of the course are described below. CHEMICAL - Titrimetry - this accompanies and reinforces the material delivered in the quantitative volumetric analysis (i.e. titration) section of this course. Nomenclature of organic compounds. This is used in a self-study situation and is linked to an assignment. Internet sources This is in addition to any material that may be made available to you on the Liverpool John Moores University Computer System and Blackboard. The internet (world-wide web) is diverse source of all types of information. The information to be found and the web sites are changing too quickly to be listed in this publication. However do not be afraid to dip in to this potential goldmine of information to supplement your knowledge and learning. It would be helpful if you would report any useful (preferably legal) web sites for pharmaceutical chemistry to the module leader for future use. Caution: much of the information available on the internet has not been checked. Please use reliable sources of information only.

5. SUBJECT AREAS
Prof, Mark Cronin/Dr Barry Nicholls: Qualitative and Quantitative Analytical Methods: Titrimetry These lectures report the need for quality control of pharmaceutical substances and their dosage forms. This includes how the information is reported in monographs in the British Pharmacopeia. Techniques for quantitative pharmaceutical quality control include volumetric analysis and the principle of titrations, and the appropriate units will be described. Details will be given on six titration regimes commonly applied in pharmaceutical analysis. The role of the Limit Tests will also be discussed and illustrated with appropriate examples. These lectures will provide the information for a total of three practical classes utilising volumetric analysis. These methods will also be useful in a number of other practical sessions in this module and throughout your course. The information will be reinforced by means of an assignment and a tutorial. Indicative references: Beckett A.H., Stenlake J.B. (1976) Practical Pharmaceutical Chemistry. Third Edition. Athlone Press. Cairns D. (2000) Essentials of Pharmaceutical Chemistry. Pharmaceutical Press. Watson D.G. (1999) Pharmaceutical Analysis. A Textbook for Pharmacy Students and Pharmaceutical Chemists. Churchill Livingstone. Dr Ian Bradshaw: Organic Reaction Mechanisms This part of the module will provide a review of general mechanistic chemistry. Prior to dealing with specific mechanisms, factors affecting the mechanisms, such as inductive and mesomeric effects and acidity and basicity, will be considered. The mechanisms will then be dealt with in some detail, covering nucleophilic and electrophilic substitution, addition, elimination and free radical mechanisms. The subsection will conclude with a consideration of isomerism, including an introduction to stereoisomerism. The mechanistic background to organic reactions is required for a consideration of functional group, heterocyclic and biological chemistry dealt with later in the module and will be referred to at many points throughout the remainder of the course. The lectures will be supported by 1 practical class, 1 tutorial and 1 assignment. Indicative references: Sykes, P (1995). Primer to Mechanism in Organic Chemistry. Longman. McMurray, J (1990). Fundamentals of Organic Chemistry. 2th Ed. Brooks Cole. Brown, W H (1987). Introduction to Organic and Biochemistry. 4th Ed. Brookes Cole.

Dr Linda Seton: Qualitative and Quantitative Analytical Methods: Spectroscopy

Continuing the theme of pharmaceutical quality control quantitative and qualitative aspects of spectroscopy will be described. This will commence with a brief introduction to spectroscopy covering the nature of electromagnetic radiation and the concept of absorption and emission of light by a substance. The arrangement of a simple spectrophotometer will be described. Specific aspects of spectroscopy will be illustrated including ultra-violet and visible radiation and the application of Beer-Lamberts Law in the Pharmaceutical Sciences. The practical aspects of infra-red spectroscopy will be described also, as will its role to enable the quantitative identification of pharmaceutical compounds. These lectures will provide the information for a practical class utilising spectroscopy. These methods will also be useful in a number of other practical sessions in this module and throughout your course. The information will be reinforced in a tutorial. Beckett A.H., Stenlake J.B. (1976) Practical Pharmaceutical Chemistry. Third Edition. Athlone Press. Watson D.G. (1999) Pharmaceutical Analysis. A Textbook for Pharmacy Students and Pharmaceutical Chemists. Churchill Livingstone. Cairns D. (2000) Essentials of Pharmaceutical Chemistry. Pharmaceutical Press. Dr Fyaz Ismail: Steroid Chemistry These lectures provide a brief introduction into steroid chemistry. Steroids have a number of vital physiological roles and may be thought of as pharmacologically active compounds. This topic covers the system for naming steroids to distinguish between their forms including the and substituents, axial and equatorial functional groups and their effects on steroid reactivity and the cis and trans ring junctions and their effect on the general shape of the molecule. More specific topics include the chemistry of the in vivo and in vitro synthesis of D vitamins. The chemistry of the bile acids will be described with particular emphasis on the relationship of their structure to their function. To illustrate further the function and properties of steroids their biosynthesis and catabolism will be described, noting how catabolic changes increase water solubility and how a single steroid may yield many different catabolic products. Indicative reference: Murray et al (1996) Harpers Review of Biochemistry. 24th Edition. Appleton and Lange. Dr Chris Rostron: Functional Group Chemistry A review of functional group chemistry will be presented, with particular reference to biologically and pharmaceutically significant molecules. Each functional group will be dealt with in the same format, namely, introduction, physical properties and chemical properties. The following functional groups will be covered: alkanes, alkenes, alkynes, aromatic hydrocarbons, haloalkanes, alcohols, phenols, ethers, carbonyl compounds, carboxylic acids and their derivatives, amines, organo-sulpur compounds. The lectures will be supported by 1 practical class, 1 tutorial and 1 assignment. Indicative references:

McMurray, J (1990). Fundamentals of Organic Chemistry. 2th Ed. Brooks Cole. Brown, W H (1987). Introduction to Organic and Biochemistry. 4th Ed. Brookes Cole. A.N. Other : Biologically Significant Molecules This section will provide an overview of the chemistry of biologically important molecules, with particular emphasis on those properties which are significant with respect to the properties of drugs and their actions on the body. The content will draw heavily on material presented in the preceding sections. Classes of compounds to be covered will be carbohydrates, lipids, aminoacids nucleic acids and steroids. In particular, this section will provide a foundation for the year 2 module entitled Biomolecular and Medicinal Chemistry. In addition to lectures, this section will include 1 practical class, 1 tutorial and 1 assignment. Indicative references: Brown, W H (1987). Introduction to Organic and Biochemistry. 4th Ed. Brookes Cole. Martin et al (1991) Harpers Review of Biochemistry. 26th Ed. Lange. Montgomery et al (1990) Biochemistry - A Case Oriented Approach. 5th Ed. C V Mosby. Dr Fyaz Ismail: Heterocyclic Chemistry This series of lectures will examine the physical and chemical properties of some simple heterocyclic molecules. This will provide a sound basis for the description of the pharmaceutical and biological importance of heterocyclic molecules. In addition to lectures, this section is supported by 1 practical class and 1 assignment. Indicative references: Gilchrist, T.L. (1985) Heterocyclic Chemistry, Pitman Publishing Dr Linda Seton: Introduction to Chromatography and Atomic Spectroscopy These lectures seek to supply a basic understanding of the scientific principles of chromatography. The lectures will describe column, paper and thin layer chromatography as analytical techniques and the role of partition and adsorption as separative processes. Further a brief introduction will be given to the use of atomic spectroscopy. These lectures will provide a firm basis for the discussion of more advanced techniques later in the course. Indicative references: Braithwaite A., Smith F.J. (1996) Chromatographic Methods. Fifth Edition. Chapman and Hall. Beckett A.H., Stenlake J.B. (1976) Practical Pharmaceutical Chemistry. Third Edition. Athlone Press. Harris D.C. (1995) Quantitative Chemical Analysis. Fourth Edition. Freeman. Watson D.G. (1999) Pharmaceutical Analysis. A Textbook for Pharmacy Students and Pharmaceutical Chemists. Churchill Livingstone.

Dr Fyaz Ismail: Complex Carbohydrate Chemistry The aim of this series of lectures is to provide an insight into of different types of polysaccharides encountered in the animal and plant world. An introduction will be given to the structure of polysaccharides and the nomenclature of the different types. Methods of determining the structure of polysaccharides will be considered as well as the role of enzymes in the utilisation of polysaccharides as a food source. The importance of the relationship between structure and function will be emphasised by consideration of polysaccharides such as starch, cellulose, dextrans and glycogen. The different functions of polysaccharides will be discussed as well as their role in animal physiology. Specific examples which will be used include heparin and the blood group antigenic polysaccharides. Indicative references: Brown, W H (1987). Introduction to Organic and Biochemistry. 4th Ed. Brookes Cole.

6. PRACTICAL CLASSES IMPORTANT


You are required to purchase a hard backed, A4 size, laboratory book in which to record all experimentally obtained results from practical sessions attended in the module. This will be used for other modules as well. This will be a permanent record of your practical work on your degree programme. This will provide a permanent record of your experimentally obtained results your attendance Failure to have this permanent record available for examination may result in penalties being applied to all or part of your coursework. Practical classes that will be included in this module include the following (note that the content and order of these classes are subject to change). Semester 1 Practical Class 1 Weighing, measuring, accuracy, precision, risk assessment Practical Class 2 Pharmaceutical quantitative analysis using titrimetry 1. Practical Class 3 Pharmaceutical quantitative analysis using titrimetry 2. Practical Class 4 Use of ultra-violet spectroscopy to assess ionisation. Practical Class 5 Investigation of unimolecular kinetics. Semester 2 Practical Class 6 Synthesis and analysis of aspirin. Practical Class 7 Carbohydrate Chemistry exercise Practical Class 8 Identification of an unknown drug substance using functional group, and other analyses. Practical Class 9 Pharmaceutical quantitative analysis using formol and iodine titrimetry. Further details in the form the practical schedules for each of the practical classes can be found on Blackboard for your prior perusal. Practical Reports Must be Submitted by the Set Deadline. Unless there are significant mitigating circumstances, or other extenuating reasons (that should be notified beforehand), coursework submitted late will not be considered for marking. Practical reports will only be considered from those students who attended that class. Reports submitted from absentees

will not be considered. Reports must be written in ink. Submissions in pencil will not be marked. Information on the writing of practical reports can be found on Blackboard.

7. TIMETABLE
A copy of the timetable is available on Blackboard. It is YOUR RESPONSIBILITY to attend the timetabled events and to take notice of any alterations from the timetable.

8. EXAMINATIONS
Conduct in Examination - see also statement on plagiarism. Conduct in examinations is governed by the Regulations of Liverpool John Moores University. In addition, you should be aware of the following information that is specific to the School of Pharmacy and BioMolecualr Sciences. 1. In addition to the items stipulated in the regulations, it is not permissible to bring to your examination desk the following items: pencil cases of any description, unless transparent glasses cases or similar of any description, unless transparent food drink, other than a bottle of still water

2. Calculators for use in examinations must have one line of alphanumeric text only. In exams where a calculator is not needed, no calculator may be present on your desk. 3. You are required to deposit all coats, bags and personal items at the front of the examination room, or in any other specified position, BEFORE you go to your examination desk. 4. Please refer to other rules in the School of Pharmacy and Biomolecular Sciences as stipulated on the relevant noticeboards. Examination Details The examination component of this module comprises one three hour examination which will take place in the appropriate examination weeks at the end of the second semester. The exact date, time and examination venue will be supplied by the Examinations Office of Liverpool John Moores University. It is your responsibility to acquaint yourself with this information. The examination will examine your knowledge of the information supplied in both semesters. The examination paper will comprise two sections. SECTION A: You are required to answer all questions in the first section (named Section A). These will be multiple choice questions. Typically Section A will comprise of forty questions. It is suggested that you spend one hour on Section A. Section A constitutes a third of the marks for the examination. SECTION B: The second section (named Section B) will be longer questions and you will be expected to answer four from eight of these questions. Within Section B, there will be four Parts (named Part 1, Part 2, Part 3 and Part 4). Each Part of Section B will contain 2 questions. Each Part of Section B relates to a particular series of topics in the module as indicated below (note this information is provided as an illustration and may be subject to change).

Section B Part 1. Topics that may be included: Quantitative and Qualitative Analytical Methods: Titrimetry, Spectroscopy, Chromatography. Section B Part 2. Topics that may be included: Organic Reaction Mechanisms, Functional Group Chemistry, Section B Part 3. Topics that may be included: Steroids and Heterocyclic Chemistry. Section B Part 4. Topics that may be included: Biologically Significant Molecules and Complex Carbohydrates You will be required to answer one question from each Part of Section B: Four Questions in Total. Failure to comply with this will result in examination questions not being marked. It is suggested that you spend two hours on Section B. Section B constitutes two-thirds of the marks for the examination. Past exam papers are NOT available in the library, nor are they held by the module leader or individual members of staff. So that you are familiar with the style of questions that may be asked a sample examination paper is included for your reference in this handbook. Please note this was NOT an actual examination paper, and the papers set in this module MAY DIFFER, with regard to the actual number of questions and their content. The purpose of this sample examination paper is to allow you to see the style of question that will be asked and the academic standard. Answers to the sample paper, to indicate the style of answer required, are given. An equation list is not normally supplied with this examination. Examination Marks The examination component makes up 70% of the module mark. To pass the module, the module mark must be 40%. A referral in the examination component of this module will require sitting of the examination at the next available opportunity.

NOT TO BE PLACED IN THE LIBRARY


Liverpool John Moores University School of Pharmacy and Chemistry BSc (Hons) ACAPS Courses Masters (Hons) Pharmacy Level 1 Examinations PHCMC1022 MONTH AND YEAR TIME ALLOWED: THREE HOURS PHARMACEUTICAL CHEMISTRY

________________________________________________________________________ INSTRUCTIONS TO CANDIDATES 1. Answer ALL questions in Section A. Answer four questions from Section B, one question from Part 1, one question from Part 2, one question from Part 3 and one question from Part 4. Section A and Section B carry one third and two-thirds of the total mark of the examination respectively. Answers to the multiple choice questions in Section A will be made using the EDPAC sheet. Each response carries one mark unless otherwise stated.

SAMPL
2. 3. 4. 5. 6 Candidates are not advised to spend more than SIXTY minutes on Section A. This question paper MUST BE HANDED IN, together with the University Answer Books and any supplementary sheets of paper used. CALCULATORS with more than ONE single line of alphanumeric display are NOT permitted to be used in this examination. CANDIDATES DESK NUMBER

Answers to the Section B questions must be in separate University Answer Books.

............................................................................................................................................

NOTE TO STUDENTS: SECTION A WILL NORMALLY COMPRISE QUESTIONS OF A VALUE OF 40 MARKS. THE QUESTIONS PROVIDED BELOW ARE INTENDED TO ILLUSTRATE THE TYPE AND STANDARD OF SECTION A QUESTIONS ONLY.

SECTION A. ANSWER ALL QUESTIONS Each response carries one mark unless otherwise stated.

SAMPLE
Examples of MCQ Questions will appear later in the academic year.

NOTE TO STUDENTS: THE LONG QUESTIONS WILL NORMALLY COMPRISE EIGHT QUESTIONS ORGANISED INTO 4 SECTIONS. THE EXAMPLES PROVIDED BELOW ARE INTENDED TO ILLUSTRATE THE TYPE AND STANDARD OF LONG QUESTIONS ONLY.

SECTION B: ANSWER FOUR QUESTIONS IN TOTAL. YOU MUST ANSWER ONE FROM EACH PART ANSWER SECTION B QUESTIONS IN SEPARATE UNIVERSITY ANSWER BOOKS
Part 1: Answer at least one question from this part. 1. Describe the role of spectroscopy in pharmaceutical analysis. (100% of the available marks) Part 2: Answer at least one question from this part. 2. Suppose you were given a mixture of the following three compounds. Describe a procedure (experimental details not required) you could use to separate and isolate each in a pure form.

NH2

OH

CH3CH2CH2CH2OH (100% of the available marks)

SAMPLE
3. Discuss, using appropriate examples, the following statement: Carbonium ions are key intermediates in organic chemical reactions. (100% of the available marks) Part 3: . Answer at least one question from this part. 4. a.) Explain fully the following statements: i) The structure of pyridine fulfils the criteria for aromacity. ii) Pyridine is -deficient. (20% of the available marks) (20% of the available marks) (20% of the available marks) iii) Pyrrole is -excessive. b) Draw the structure of the Diels-Alder adduct between furan and maleic anhydride. What does the Diels-Alder reaction tell us about the comparative aromatic stabilities of thiophene, furan and pyrrole?

(15% of the available marks) c) Give reasons for the differences in aromatic stabilities of thiophene, furan and pyrrole. (15% of the available marks) d) Give the name and function of a biologically important pteridine derivative. (10% of the available marks) Part4: . Answer at least one question from this part. Please note that no sample questions are available for this part

ANSWERS TO SECTION A OF THE SAMPLE PAPER These will be available later in the academic year. ANSWERS TO SECTIONS B OF THE SAMPLE PAPER Please note that these may be essay questions. You are expected to answer these in the form of essay i.e. you will need to spend time on constructing and planning an essay to obtain a good mark. 1. Describe the role of spectroscopy in pharmaceutical analysis. This is an open-ended question. There is no one correct answer! The role of a plan is vital to obtain good marks. A reasonable essay plan might be: Introduction - set the scene and make the following observations: what is spectrophometry - absorption of light different types of spectroscopy - UV vs IR quantitative UV qualitative IR Importance and role of spectroscopy in pharmaceutical analysis

Discussion of quantitative UV light absorbed in the visible and UV regions of the spectrum Beer-Lamberts law how this is used in pharmaceutical analysis - give examples experimental details - simple diagram of a spectrophotometer; problems with UV; solvents etc.

Discussion of qualitative IR light absorbed in IR region of the spectrum used to identify pharmaceutically important compounds, give details of fingerprint region; identify individual peaks; comparison with reference spectra mention that IR can also be used quantitatively

experimental details - IR cells; problems with solvents and overcoming them Concluding paragraph - draws your essay to a close spectroscopy important in pharmaceutical analysis for quantitative and qualative analysis 2. Suppose you were given a mixture of the following three compounds. Describe a procedure(experimental details not required) you could use to separate and isolate each in a pure form.

NH2

OH

CH3CH2CH2CH2OH

The basis of the separation relies upon the fact that the first compound (aniline) is basic, the second compound (phenol) is acidic and the third compound (butanol) is neutral. The water solubility of all three compounds is quite low. If the mixture is treated with aqueous acid. Aniline will react to form a water soluble hydrochloride salt. The phenol and the alcohol can be removed by extraction with an organic solvent such as chloroform. The aqueous acid solution can then be neutralised and the aniline will be released from the hydrochloride salt and can be isolated by solvent extraction. The remaining mixture can then be treated with aqueous sodium hydroxide. The phenol will react forming a soluble sodium salt. The alcohol can be removed by extraction with organic solvent. The phenol can be regenerated by acidification of the sodium salt solution and extraction with an organic solvent. 3. Discuss, using appropriate examples, the following statement: Carbonium ions are key intermediates in organic chemical reactions. Features to be included in this answer: Formation of carbonium ions ionisation elimination decomposition Stability of carbonium ions explanation of factors affecting stability Involved in unimolecular substitution reactions explanation and example Involved in unimolecular elimination reactions explanation and example Describe relationship between the two above reactions Involved in electrophilic substitution reactions

explanation and example. 4. a.) Explain fully the following statements: i) The structure of pyridine fulfils the criteria for aromacity. The structure of pyridine is planar and monocyclic. It has a fully conjugated -system with complete cyclic overlap and it obeys Huckels rule (4n + 2 = 6, n = 1). Pyridine therefore fulfils its criteria for aromaticity. ii) Pyridine is -deficient. Draw the resonance structure showing -deficiency and explain them. iii) Pyrrole is -excessive. Draw the resonance structure showing pyrrole is -excessive and explain them. b) Draw the structure of the Diels-Alder adduct between furan and maleic anhydride. What does the Diels-Alder reaction tell us about the comparative aromatic stabilities of thiophene, furan and pyrrole? Correctly drawing the structure of the adduct gets one mark. Aromatic stability means a general lack of reactivity in addition reactions such as the Diels-Alser reaction. Pyrrole and thiophene do not undergo this reaction, thus demonstrating that they are more aromatic than furan. c) Give reasons for the differences in aromatic stabilities of thiophene, furan and pyrrole. Consider, for example: differences in electronegativities of the heteroatom, differences in molecular shape. You need to explain how these differences affect aromaticity. d) Give the name and function of a biologically important pteridine derivative. One mark for stating a pteridine derivative (e.g. folic acid, riboflavine) and one mark for its biological importance.