ELEMENTARY ORGANIC - KopyKitab

ELEMENTARYORGANICSPECTROSCOPYPRINCIPLES AND CHEMICAL APPLICATIONSFOR B.Sc. (HONS.), POSTGRADUATE STUDENTS OF ALLINDIAN UNIVERSITIES AND COMPETITIVE EXAMINATIONSY.R. SHARMAPostgraduate Department of Chemistry,D.A.V. College, Jalandhar, India.S. CHAND & COMPANY PVT. LTD.(AN ISO 9001 : 2008 COMPANY)RAM NAGAR, NEW DELHI-110055

S. CHAND & COMPANY PVT. LTD.(An ISO 9001 : 2008 Company)Head Office: 7361, RAM NAGAR, NEW DELHI - 110 055Phone: 23672080-81-82, 9899107446, 9911310888 Fax: 91-11-23677446Branches :Shop at: schandgroup.com; e-mail: info@schandgroup.comAHMEDABAD: 1st Floor, Heritage, Near Gujarat Vidhyapeeth, Ashram Road, Ahmedabad - 380 014,Ph: 27541965, 27542369, ahmedabad@schandgroup.comBENGALURU: No. 6, Ahuja Chambers, 1st Cross, Kumara Krupa Road, Bengaluru - 560 001,Ph: 22268048, 22354008, bangalore@schandgroup.comBHOPAL: Bajaj Tower, Plot No. 2&3, Lala Lajpat Rai Colony, Raisen Road, Bhopal - 462 011,Ph: 4274723, 4209587. bhopal@schandgroup.comCHANDIGARH: S.C.O. 2419-20, First Floor, Sector - 22-C (Near Aroma Hotel), Chandigarh -160 022,Ph: 2725443, 2725446, chandigarh@schandgroup.comCHENNAI: No.1, Whites Road, Opposite Express Avenue, Royapettah, Chennai - 600014Ph. 28410027, 28410058, chennai@schandgroup.comCOIMBATORE: 1790, Trichy Road, LGB Colony, Ramanathapuram, Coimbatore -6410045,Ph: 2323620, 4217136 coimbatore@schandgroup.com (Marketing Office)CUTTACK: 1st Floor, Bhartia Tower, Badambadi, Cuttack - 753 009, Ph: 2332580; 2332581,cuttack@schandgroup.comDEHRADUN: 1st Floor, 20, New Road, Near Dwarka Store, Dehradun - 248 001,Ph: 2711101, 2710861, dehradun@schandgroup.comGUWAHATI: Dilip Commercial (Ist floor), M.N. Road, Pan Bazar, Guwahati - 781 001,Ph: 2738811, 2735640 guwahati@schandgroup.comHYDERABAD: Padma Plaza, H.No. 3-4-630, Opp. Ratna College, Narayanaguda, Hyderabad - 500 029,Ph: 27550194, 27550195, hyderabad@schandgroup.comJAIPUR: 1st Floor, Nand Plaza, Hawa Sadak, Ajmer Road, Jaipur - 302 006,Ph: 2219175, 2219176, jaipur@schandgroup.comJALANDHAR: Mai Hiran Gate, Jalandhar - 144 008, Ph: 2401630, 5000630, jalandhar@schandgroup.comKOCHI: Kachapilly Square, Mullassery Canal Road, Ernakulam, Kochi - 682 011,Ph: 2378740, 2378207-08, cochin@schandgroup.comKOLKATA: 285/J, Bipin Bihari Ganguli Street, Kolkata - 700 012, Ph: 22367459, 22373914, kolkata@schandgroup.comLUCKNOW: Mahabeer Market, 25 Gwynne Road, Aminabad, Lucknow - 226 018, Ph: 4076971, 4026791, 4065646,4027188, lucknow@schandgroup.comMUMBAI: Blackie House, IInd Floor, 103/5, Walchand Hirachand Marg, Opp. G.P.O., Mumbai - 400 001,Ph: 22690881, 22610885, mumbai@schandgroup.comNAGPUR: Karnal Bagh, Near Model Mill Chowk, Nagpur - 440 032, Ph: 2720523, 2777666 nagpur@schandgroup.comPATNA: 104, Citicentre Ashok, Mahima Palace , Govind Mitra Road, Patna - 800 004, Ph: 2300489, 2302100,patna@schandgroup.comPUNE: 291, Flat No.-16, Ganesh Gayatri Complex, IInd Floor, Somwarpeth, Near Jain Mandir,Pune - 411 011, Ph: 64017298, pune@schandgroup.com (Marketing Office)RAIPUR: Kailash Residency, Plot No. 4B, Bottle House Road, Shankar Nagar, Raipur - 492 007,Ph: 2443142,Mb. : 09981200834, raipur@schandgroup.com (Marketing Office)RANCHI: Flat No. 104, Sri Draupadi Smriti Apartments, (Near of Jaipal Singh Stadium) Neel Ratan Street, UpperBazar, Ranchi - 834 001, Ph: 2208761, ranchi@schandgroup.com (Marketing Office)SILIGURI: 122, Raja Ram Mohan Roy Road, East Vivekanandapally, P.O., Siliguri, Siliguri-734001,Dist., Jalpaiguri, (W.B.) Ph. 0353-2520750 (Marketing Office) siliguri@schandgroup.comVISAKHAPATNAM : No. 49-54-15/53/8, Plot No. 7, 1st Floor, Opp. Radhakrishna Towers,Seethammadhara North Extn., Visakhapatnam - 530 013, Ph-2782609 (M) 09440100555,visakhapatnam@schandgroup.com (Marketing Office) 1980, Y.R. SharmaAll rights reserved. No part of this publication may be reproduced or copied in any material form (including photocopying or storing it in any medium in form of graphics, electronic or mechanical means and whether or nottransient or incidental to some other use of this publication) without written permission of the copyright owner.Any breach of this will entail legal action and prosecution without further notice.Jurisdiction : All disputes with respect to this publication shall be subject to the jurisdiction of the Courts, tribunalsand forums of New Delhi, India only.First Edition 1980Subsequent Editions and Reprints 1984, 86, 89, 90, 92, 93, 94, 95, 96, 97, 99, 2000, 2001, 2002Fourth Revised and Enlarged (Multicolour) Edition 2007, Reprints 2008,2009 (Twice), 2010, 2011 (Twice), 2012Fifth Revised Edition 2013ISBN : 81-219-2884-2Code : 04A 305printed in indiaBy Rajendra Ravindra Printers Pvt. Ltd., 7361, Ram Nagar, New Delhi -110 055and published by S. Chand & Company Pvt. Ltd., 7361, Ram Nagar, New Delhi -110 055.

DedicatedToMy Father

(iv)

FOREWORDUndergraduate education in Chemistry seems to be in the midst of a major revolution inIndia. Sophisticated topics are increasingly being introduced into the college chemistry courses.In Organic Chemistry, this trend is apparent in the new text books. However, it has been foundthat a single text, no matter how well written, is not the best medium of presenting glimpses ofthese sophisticated topics in addition to the necessary basic chemistry. Spectroscopic techniques,viz., UV, IR and NMR are parts of the subjects which are regarded as essential and common toall universities in degree and postgraduate courses. Thus, the publishers and the author felt theneed to write a separate book on these few techniques.I have gone through the whole of the text, entitled “Elementary Organic AbsorptionSpectroscopy” and find it an interesting reading. The presentation of the subject in a lucid styleand simple language speaks of the hard work done by the author, Sh. Y.R. Sharma, Post-graduateDepartment of Chemistry, D.A.V. College, Jalandhar. All explanations have well attended reasonsand are supplemented by appropriate data to bring home the point. The inclusion of a largenumber of worked examples and problems gives ample insight into the topics dealt with. Thepresentation of the subject matter is systematic and has made the book useful not only to studentsbut also to the workers engaged in organic synthesis in chemical and allied industries.Relatively newer techniques like C13 NMR spectroscopy have also been incorporated for thebenefit of students engaged in advanced studies. Ample space devoted to the spectra of someimportant solvents and their effects on the spectra merit special attention.I think that a long-felt need for such a book by an Indian author has been fulfilled. I wishthe book a great success.ChandigarhO.P. VIG(v)

PREFACE TO THE FIFTH EDITIONThe warm reception accorded to the fourth edition of Elementary Organic Spectroscopyand its subsequent reprints has provided me a great deal of encouragement to present the fourthedition of this book. The subject-matter presented in the book is sufficiently comprehensive andthe knowledge gained through it will make easy to identify an unknown compound. The massivescope of the subject dictates that all possible visual assistance be available to the students. Thishas been done by presenting a large number of spectral diagrams which have been added inthis edition. Their interpretation serve to reinforce as well as assist the students in learning thesubject. This attempt also helps the students to develop an intutive feel in using spectroscopy tosolve structural problems. The main features of the present edition are : Multichoice questions are added in each chapter. Some numerical problems are alsoincluded where required. A chapter on ‘Raman Spectroscopy’ has been added to meet the demand of a largenumber of students and teachers. This technique forms a part of curriculum in most ofthe universities and is dealt here in reasonable detail. Each chapter in the text is made more elaborate by induction of suitable material inthe form of applications, numerical problems and explanation of new spectra. Importantfeatures for each technique, Short Question with Answers, Important problems (Solved)form special features of the fifth edition. A number of problems have been given for the students to check their competence. Extensive summarises have been placed at the end of each shapter in order to revieweach topic and highlight the main points. Every attempt is made to retain the comprehensive character of the text so as to ensurethat it continues to be one volume text for the students studying Organic Chemistry atthe Graduate and Postgraduate levels. A large number of new figures have been added in the text and all old figures havebeen redesigned. In the ultra-violet spectroscopy, Polycyclic hydrocarbons and their spectra have beendiscussed and proton nuclear magnetic resonance spectra of carbocations have beengiven.I express my gratitude to my colleagues and friends who gave useful suggestions and tookkeen interest in the revision of the book. Thanks are due to my wife, Mrs. Saroj Sharma for thesecretarial assistance which she rendered during the revision of the book. I will welcome suggestionsand healthy criticism of the subject-matter and style for the further improvement of this book.JalandharY.R. SHARMAPh: 0181-2250012e-mail: sharma yr1940@ymail.com(vi)