Page 1 Study Guide: CHEM110 - Organic Chemistry 1 CHEM 110 Module 3 Organic Chemistry Module Notes Page 2 Study Guide: CHEM110 - Organic Chemistry 1 CHEM 110 Module 3 Organic Chemistry Module Notes Study Guide: CHEM110 - Organic Chemistry 2 T T T Ta a a ab b b bl l l le e e e o o o of f f f C C C Co o o on n n nt t t te e e en n n nt t t ts s s s Topic 3A – Introduction ................................................................... 1 Topic 3B - Bonding in carbon compounds.............................................. 7 Topic 3C – Alkanes .......................................................................16 Topic 3D - Alkenes and Alkynes........................................................31 Topic 3E - Aromatic compounds........................................................49 Topic 3F Alkyl halides....................................................................61 Topic 3G – Alcohols ......................................................................69 Topic 3H – Amines........................................................................80 Topic 3I - Aldehydes and Ketones ......................................................88 Topic 3J - Carboxylic acids and their derivatives.....................................96 Page 3 Study Guide: CHEM110 - Organic Chemistry 1 CHEM 110 Module 3 Organic Chemistry Module Notes Study Guide: CHEM110 - Organic Chemistry 2 T T T Ta a a ab b b bl l l le e e e o o o of f f f C C C Co o o on n n nt t t te e e en n n nt t t ts s s s Topic 3A – Introduction ................................................................... 1 Topic 3B - Bonding in carbon compounds.............................................. 7 Topic 3C – Alkanes .......................................................................16 Topic 3D - Alkenes and Alkynes........................................................31 Topic 3E - Aromatic compounds........................................................49 Topic 3F Alkyl halides....................................................................61 Topic 3G – Alcohols ......................................................................69 Topic 3H – Amines........................................................................80 Topic 3I - Aldehydes and Ketones ......................................................88 Topic 3J - Carboxylic acids and their derivatives.....................................96 Study Guide: CHEM110 - Organic Chemistry 1 O O O Or r r rg g g ga a a an n n ni i i ic c c c C C C Ch h h he e e em m m mi i i is s s st t t tr r r ry y y y M M M Mo o o od d d du u u ul l l le e e e 3 3 3 3 Topic 3A – Introduction K K K Ke e e ey y y y q q q qu u u ue e e es s s st t t ti i i io o o on n n ns s s s Why is carbon so special? How is it that the vast majority of chemicals known today are made from carbon (and other elements)? Carbon chemistry is not only omnipresent in our society but it is emphatically the basis of life itself. In this topic we introduce you to the long history of the subject "carbon chemistry" or more widely known as "organic chemistry" as well as deal with the principles for breaking down such a vast field of science into understandable units. O O O Ou u u ut t t tl l l li i i in n n ne e e e The notes produced for the CHEM110 organic chemistry component of the unit are based on sections of the book Introduction to Organic Chemistry, William H. Brown (described as Brown in these notes). However, the Module notes do not necessarily follow exactly the order given in the text. We will also refer to both the Saunders ChemOffice Web CD-ROM (included with the Brown text) and the General Chemistry CD-ROM (included with your other main text, Chemistry and Chemical Reactivity, Kotz and Treichel, 5 th edition). These CD- ROM references are not essential to learn this course, but we highly recommend their use to gain a better understanding of the principles involved. Some topics have been expanded from these prescribed materials, and others given lesser emphasis or even omitted. This reflects our philosophy regarding the relative importance of the various aspects of organic chemistry to be covered in the unit. The ordering adopted is based on that which has been found to be successful in teaching the internal unit. This permits the introduction of new topics and concepts to be used as a revision of earlier parts of the unit. Nonetheless, the endpoint arrived at is essentially the same as that of the prescribed text. Page 4 Study Guide: CHEM110 - Organic Chemistry 1 CHEM 110 Module 3 Organic Chemistry Module Notes Study Guide: CHEM110 - Organic Chemistry 2 T T T Ta a a ab b b bl l l le e e e o o o of f f f C C C Co o o on n n nt t t te e e en n n nt t t ts s s s Topic 3A – Introduction ................................................................... 1 Topic 3B - Bonding in carbon compounds.............................................. 7 Topic 3C – Alkanes .......................................................................16 Topic 3D - Alkenes and Alkynes........................................................31 Topic 3E - Aromatic compounds........................................................49 Topic 3F Alkyl halides....................................................................61 Topic 3G – Alcohols ......................................................................69 Topic 3H – Amines........................................................................80 Topic 3I - Aldehydes and Ketones ......................................................88 Topic 3J - Carboxylic acids and their derivatives.....................................96 Study Guide: CHEM110 - Organic Chemistry 1 O O O Or r r rg g g ga a a an n n ni i i ic c c c C C C Ch h h he e e em m m mi i i is s s st t t tr r r ry y y y M M M Mo o o od d d du u u ul l l le e e e 3 3 3 3 Topic 3A – Introduction K K K Ke e e ey y y y q q q qu u u ue e e es s s st t t ti i i io o o on n n ns s s s Why is carbon so special? How is it that the vast majority of chemicals known today are made from carbon (and other elements)? Carbon chemistry is not only omnipresent in our society but it is emphatically the basis of life itself. In this topic we introduce you to the long history of the subject "carbon chemistry" or more widely known as "organic chemistry" as well as deal with the principles for breaking down such a vast field of science into understandable units. O O O Ou u u ut t t tl l l li i i in n n ne e e e The notes produced for the CHEM110 organic chemistry component of the unit are based on sections of the book Introduction to Organic Chemistry, William H. Brown (described as Brown in these notes). However, the Module notes do not necessarily follow exactly the order given in the text. We will also refer to both the Saunders ChemOffice Web CD-ROM (included with the Brown text) and the General Chemistry CD-ROM (included with your other main text, Chemistry and Chemical Reactivity, Kotz and Treichel, 5 th edition). These CD- ROM references are not essential to learn this course, but we highly recommend their use to gain a better understanding of the principles involved. Some topics have been expanded from these prescribed materials, and others given lesser emphasis or even omitted. This reflects our philosophy regarding the relative importance of the various aspects of organic chemistry to be covered in the unit. The ordering adopted is based on that which has been found to be successful in teaching the internal unit. This permits the introduction of new topics and concepts to be used as a revision of earlier parts of the unit. Nonetheless, the endpoint arrived at is essentially the same as that of the prescribed text. Study Guide: CHEM110 - Organic Chemistry 2 I I I In n n n t t t th h h he e e e b b b be e e eg g g gi i i in n n nn n n ni i i in n n ng g g g. . . .. . . .. . . .. . . .. . . .. . . .. . . .. . . . Friedrich Wöhler expressed a view of organic chemistry with which some newcomers to the discipline might have some sympathy. In a letter to Jons Jacob Berzelius in 1835, he wrote: "Organic Chemistry just now is enough to drive one mad. It gives me the impression of a primeval tropical forest, full of the most remarkable things; a monstrous and boundless thicket, with no way of escape, into which one may well dread to enter". Berzelius in 1808 had been involved in the isolation and study of chemicals derived from living sources; the view at the time was that such "organic" substances as they were known could not be synthesised in the laboratory from "inorganic" materials, because it was believed that a "vital force" which was possessed only by living organisms was necessary to produce organic compounds. This "Vital Force Theory" was challenged by Wöhler in 1828 when he heated the inorganic compound ammonium cyanate (NH 4 OCN) and obtained urea which was recognised as being "organic" because it could be isolated from urine. A few years later August Kekulé assigned the modern definition of organic chemistry - organic compounds are those containing carbon. Likewise Leopold Gmelin in 1848 defined organic chemistry as “the chemistry of the compounds of carbon which occur naturally”. This definition is too restrictive, however - although many organic compounds are of natural origin, the great majority owe their existence to the endeavours of academic and industrial chemists. Some may only have been synthesised in milligram quantities (or less!) whereas others are manufactured annually on the scale of millions of tonnes. And let us not forget that all living matter is constructed of a multitude of (mainly very complex) organic chemicals and that life processes are the reactions of these chemicals. In 1848 Wöhler was to write: “The Philosopher of Chemistry will draw the conclusion that the production of all organic matters in our laboratories, in as much as they do not belong any more to the organism, must be regarded not only as probable but as certain. It is true we do not know the methods by which this final result will be reached, because the rudiments are unknown from which they are to be developed, but we shall know them in time”. A magnificent statement for 1848! Wöhler indicated various target natural products, among them morphine: 80 years were to elapse before the structure of morphine was elucidated and a further 20 years before its synthesis was achieved. Page 5 Study Guide: CHEM110 - Organic Chemistry 1 CHEM 110 Module 3 Organic Chemistry Module Notes Study Guide: CHEM110 - Organic Chemistry 2 T T T Ta a a ab b b bl l l le e e e o o o of f f f C C C Co o o on n n nt t t te e e en n n nt t t ts s s s Topic 3A – Introduction ................................................................... 1 Topic 3B - Bonding in carbon compounds.............................................. 7 Topic 3C – Alkanes .......................................................................16 Topic 3D - Alkenes and Alkynes........................................................31 Topic 3E - Aromatic compounds........................................................49 Topic 3F Alkyl halides....................................................................61 Topic 3G – Alcohols ......................................................................69 Topic 3H – Amines........................................................................80 Topic 3I - Aldehydes and Ketones ......................................................88 Topic 3J - Carboxylic acids and their derivatives.....................................96 Study Guide: CHEM110 - Organic Chemistry 1 O O O Or r r rg g g ga a a an n n ni i i ic c c c C C C Ch h h he e e em m m mi i i is s s st t t tr r r ry y y y M M M Mo o o od d d du u u ul l l le e e e 3 3 3 3 Topic 3A – Introduction K K K Ke e e ey y y y q q q qu u u ue e e es s s st t t ti i i io o o on n n ns s s s Why is carbon so special? How is it that the vast majority of chemicals known today are made from carbon (and other elements)? Carbon chemistry is not only omnipresent in our society but it is emphatically the basis of life itself. In this topic we introduce you to the long history of the subject "carbon chemistry" or more widely known as "organic chemistry" as well as deal with the principles for breaking down such a vast field of science into understandable units. O O O Ou u u ut t t tl l l li i i in n n ne e e e The notes produced for the CHEM110 organic chemistry component of the unit are based on sections of the book Introduction to Organic Chemistry, William H. Brown (described as Brown in these notes). However, the Module notes do not necessarily follow exactly the order given in the text. We will also refer to both the Saunders ChemOffice Web CD-ROM (included with the Brown text) and the General Chemistry CD-ROM (included with your other main text, Chemistry and Chemical Reactivity, Kotz and Treichel, 5 th edition). These CD- ROM references are not essential to learn this course, but we highly recommend their use to gain a better understanding of the principles involved. Some topics have been expanded from these prescribed materials, and others given lesser emphasis or even omitted. This reflects our philosophy regarding the relative importance of the various aspects of organic chemistry to be covered in the unit. The ordering adopted is based on that which has been found to be successful in teaching the internal unit. This permits the introduction of new topics and concepts to be used as a revision of earlier parts of the unit. Nonetheless, the endpoint arrived at is essentially the same as that of the prescribed text. Study Guide: CHEM110 - Organic Chemistry 2 I I I In n n n t t t th h h he e e e b b b be e e eg g g gi i i in n n nn n n ni i i in n n ng g g g. . . .. . . .. . . .. . . .. . . .. . . .. . . .. . . . Friedrich Wöhler expressed a view of organic chemistry with which some newcomers to the discipline might have some sympathy. In a letter to Jons Jacob Berzelius in 1835, he wrote: "Organic Chemistry just now is enough to drive one mad. It gives me the impression of a primeval tropical forest, full of the most remarkable things; a monstrous and boundless thicket, with no way of escape, into which one may well dread to enter". Berzelius in 1808 had been involved in the isolation and study of chemicals derived from living sources; the view at the time was that such "organic" substances as they were known could not be synthesised in the laboratory from "inorganic" materials, because it was believed that a "vital force" which was possessed only by living organisms was necessary to produce organic compounds. This "Vital Force Theory" was challenged by Wöhler in 1828 when he heated the inorganic compound ammonium cyanate (NH 4 OCN) and obtained urea which was recognised as being "organic" because it could be isolated from urine. A few years later August Kekulé assigned the modern definition of organic chemistry - organic compounds are those containing carbon. Likewise Leopold Gmelin in 1848 defined organic chemistry as “the chemistry of the compounds of carbon which occur naturally”. This definition is too restrictive, however - although many organic compounds are of natural origin, the great majority owe their existence to the endeavours of academic and industrial chemists. Some may only have been synthesised in milligram quantities (or less!) whereas others are manufactured annually on the scale of millions of tonnes. And let us not forget that all living matter is constructed of a multitude of (mainly very complex) organic chemicals and that life processes are the reactions of these chemicals. In 1848 Wöhler was to write: “The Philosopher of Chemistry will draw the conclusion that the production of all organic matters in our laboratories, in as much as they do not belong any more to the organism, must be regarded not only as probable but as certain. It is true we do not know the methods by which this final result will be reached, because the rudiments are unknown from which they are to be developed, but we shall know them in time”. A magnificent statement for 1848! Wöhler indicated various target natural products, among them morphine: 80 years were to elapse before the structure of morphine was elucidated and a further 20 years before its synthesis was achieved. Study Guide: CHEM110 - Organic Chemistry 3 How can we succeed? What is the best way to study organic chemistry? In many ways it can be likened to learning a new language, and like the use of language communication is both oral and written. The written component of the organic chemistry language is the structural formula, but while one can frequently get by with an ungrammatical sentence, a badly drawn (ungrammatical?) structure is useless. The structure of a compound determines its reactivity, so the need for accuracy in drawing structures is paramount. This accuracy can only be achieved by practice with pen on paper: the task is rather like learning multiplication tables in primary school-eventually the correct structure will (we hope) be drawn automatically. Even professional chemists started this way and they communicate extensively by drawing structures. At least the written language is universal! Production of correct pictures needs precision in drawing which leads to precision in thinking. W W W Wh h h hy y y y i i i is s s s c c c ca a a ar r r rb b b bo o o on n n n s s s so o o o s s s sp p p pe e e ec c c ci i i ia a a al l l l? ? ? ? Read Brown, Chapter 1.1 – 1.4 It is a characteristic of carbon that it forms strong covalent bonds with other carbon atoms, and with certain other elements, particularly hydrogen (carbon and hydrogen differ in electronegativity by only 0.4 on the Pauling scale). The carbon - carbon bond energy for a single bond is around 350 kJmol -1 . This is among the strongest of covalent bonds between like atoms of any element. Carbon can also form multiple bonds, that is, double and triple bonds readily. The first point allows carbon to form an enormous variety of chains and rings, and this is the reason for the diversity of organic compounds. There are more than 10 million compounds listed in Chemical Abstracts, and most of these are organic. Fortunately we can classify them into a few dozen families. This classification is based on structural entities which have a chemical reactivity that is roughly predictable - so-called functional groups. We won’t cover them all, but by the end of the course the principles will be well apparent to you. Two of the simplest examples, both containing carbon chains are: H C H C H C H HH H H C C C C C C HH H H HH H H H H H H and propane cyclohexane General Chemistry CD-ROM Screen 11.3Read More
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