MINISTRY OF EDUCATION AND SCIENCE OF UKRAINE National Aviation University A.D. Kustovska, T.V. Kravchuk, O.P. Yashchuk ORGANIC CHEMISTRY. ANOXIC COMPOUNDS Guide Approved by Academic Council of National Aviation University for University students of specialty 162 “Biotechnology and Bioengineering” Kyiv 2017 1 UDC All rights reserved. No part of this book may be reproduced in any form without the prior written permission of the publisher Compilers: A.D. Kustovska – candidate of chemical sciences, docent – chapter 5-8; T.V. Kravchuk – master of chemical technology, junior lecturer – chapter 1-4 (together with Yashchuk O.P.); O.P. Yashchuk – specialist of the english language and literature, junior lecturer – chapter 1-4 (together with Kravchuk T.V.) Reviewers: Sokolsky G.V. – Doctor of Science (Chemistry) (National University of Food Technologies); Nesterova L.O. – Doctor of Technical Sciences, docent (National University of Life and Environmental Sciences of Ukraine); Novoselov E.F. – Candidate of Chemical Sciences, docent (National Aviation University) Approved by Academic Council of National Aviation University (Minute №___ of ________) Навчальний посібник уміщує теоретичний та практичний матеріал для вивчення дисципліни «Органічна хімія». Для студентів вищих навчальних закладів спеціальності 162 «Біотехнологія та біоінженерія». Kustovska A.D. Organic Chemistry. Anoxic Compounds: guide / A.D. Kustovska, T.V. Kravchuk, O.P. Yashchuk. – К.: NAU, 2017. – 200 p. The guide contains theoretical and practical material for the study of discipline “Organic chemistry”. For University students of specialty 162 “Biotechnology and Bioengineering” Kustovska А.D., Kravchuk Т.V., Yashchuk О.P., 2017 NAU, 2017 2 Contents Introduction ............................................................................................. 7 CHAPTER 1. STRUCTURE OF ORGANIC COMPOUNDS ......Error! Bookmark not defined. 1.1. Introduction to organic chemistryError! Bookmark not defined. 1.2. Structure of organic compounds . Error! Bookmark not defined. 1.2.1. The structure of the atom ..... Error! Bookmark not defined. 1.2.2. Concept of hybridization of atomic orbitals .................Error! Bookmark not defined. 1.3. Methods of representation of organic molecules .................Error! Bookmark not defined. 1.4. Isomerism ................................... Error! Bookmark not defined. 1.4.1. Structural isomerism ............ Error! Bookmark not defined. 1.4.2. Types of stereoisomerism .... Error! Bookmark not defined. 1.5. Atoms cross-coupling in a molecule.......... Error! Bookmark not defined. 1.5. Acids and Bases .......................... Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 2. CLASSIFICATION OF ORGANIC REACTIONS. ............................................................... Error! Bookmark not defined. 2.1. Classification by the type of reactions ....... Error! Bookmark not defined. 2. 2. Classification by type of chemical bonds braking .............Error! Bookmark not defined. 3 2. 3. Classification by the nature of a reagent... Error! Bookmark not defined. 2. 4. Classification by reaction order . Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 3. CLASSIFICATION AND NOMENCLATURE OF ORGANIC COMPOUNDS ................... Error! Bookmark not defined. 3.1. Classification of Organic Compounds ....... Error! Bookmark not defined. 3.2. Nomenclature of hydrocarbons .. Error! Bookmark not defined. 3.3. Nomenclature of the derivatives of hydrocarbons ...............Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 4. SATURATED HYDROCARBONS ... Error! Bookmark not defined. 4.1. Alkanes ....................................... Error! Bookmark not defined. 4.1.1. Nomenclature of Alkanes .... Error! Bookmark not defined. 4.1.2. Physical Properties of Alkanes ........... Error! Bookmark not defined. 4.1.3. Sources and Preparation of Alkanes ... Error! Bookmark not defined. 4.1.4. Chemical Properties of Alkanes ......... Error! Bookmark not defined. 4.2. Cycloalkanes............................... Error! Bookmark not defined. 4.2.1. Nomenclature of Cycloalkanes ........... Error! Bookmark not defined. 4 4.2.2. Isomerization of Cycloalkanes ........... Error! Bookmark not defined. 4.2.3. Physical Properties of Cycloalkanes ... Error! Bookmark not defined. 4.2.4. Chemical Properties of Cycloalkanes Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 5. UNSATURATED HYDROCARBONS .................Error! Bookmark not defined. 5.1. Alkenes ....................................... Error! Bookmark not defined. 5.1.1. Nomenclature of Alkenes .... Error! Bookmark not defined. 5.1.2. Physical Properties of Alkenes ........... Error! Bookmark not defined. 5.1.3. Preparation of Alkenes ........ Error! Bookmark not defined. 5.1.4. Chemical Properties of Alkenes ......... Error! Bookmark not defined. 5.2. Alkynes ....................................... Error! Bookmark not defined. 5.2.1. Nomenclature of Alkynes ....... Error! Bookmark not defined. 5.2.2. Physical Properties of Alkynes Error! Bookmark not defined. 5.2.3. Preparation of Alkynes ............ Error! Bookmark not defined. 5.2.4. Chemical Properties of Alkynes ............. Error! Bookmark not defined. 5.3. Dienes ......................................... Error! Bookmark not defined. 5.3.1. Preparation of Dienes .............. Error! Bookmark not defined. 5 5.3.2. Chemical Properties of Dienes Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 6. AROMATIC HYDROCARBONS Error! Bookmark not defined. 6.1. Introduction ................................ Error! Bookmark not defined. 6.2. Nomenclature of the Benzene Derivatives Error! Bookmark not defined. 6.3. The Stability of Benzene ............ Error! Bookmark not defined. 6.4. Physical Properties and Sources of Aromatic Hydrocarbons ........................................................... Error! Bookmark not defined. 6.5. Preparation of Benzene............... Error! Bookmark not defined. 6.6. Chemical Properties of Benzene. Error! Bookmark not defined. 6.7. Polycyclic Aromatic Compounds Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 7. NITROGEN COMPOUNDS ........ Error! Bookmark not defined. 7.1. Introduction ................................ Error! Bookmark not defined. 7.2. Nomenclature of Amines ............ Error! Bookmark not defined. 7.3. Physical Properties of Amines .... Error! Bookmark not defined. 7.4. Preparation of Amines ................ Error! Bookmark not defined. 7.5. Chemical Properties of Amines .. Error! Bookmark not defined. 7.5.1. Basicity of Amines .............. Error! Bookmark not defined. 7.5.2. Acylation of amines ............. Error! Bookmark not defined. 6 7.5.3. Reactions of Amines with Nitrous Acid ... Error! Bookmark not defined. 7.6. Arendiazonium Salts................... Error! Bookmark not defined. 7.7. Uses of Amines and their Derivatives ....... Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. CHAPTER 8. HALOGEN COMPOUNDS .......... Error! Bookmark not defined. 8.1. Introduction ................................ Error! Bookmark not defined. 8.2. Nomenclature of Halogen Compounds ..... Error! Bookmark not defined. 8.3. Physical Properties of Halogen Compounds ... Error! Bookmark not defined. 8.4. Preparation of Halogen Compounds .......... Error! Bookmark not defined. 8.5. Chemical Properties of Halogen Compounds.. Error! Bookmark not defined. 8.5.1. Nucleophilic Substitution Reactions... Error! Bookmark not defined. 8.5.2. Elimination Reactions.......... Error! Bookmark not defined. 8.5.3. Uses of Halogen Compounds ............. Error! Bookmark not defined. Questions and problems......................... Error! Bookmark not defined. 7 Introduction Organic chemistry plays a great role in the present day life. All plants consist of organic molecules. Organic molecules pass signals between neutrons in all animals; they are main part of food we eat daily. And the most important role of organic molecules is that they store all genetic information on the planet. Every day people use some things, which consist of organic substances. The common examples of such things are our clothes, mobile phones, stationery and so on. Modern screens of mobile phones are made of organic liquid crystals. Polymers are used for paper production. So, organic chemistry takes a very important place in our lives. Organic chemistry as a branch of science changes very fast. In the early days of organic chemistry, it worked mainly with soaps and dyes, but now it takes the central place in various fields of industry. So, we need to know organic chemistry for better understanding interdisciplinary problems. General chemistry tells us that a substance structure determines its properties. And organic chemistry helps us to understand in the best way connections between the structure and properties of a substance. Organic compounds of different classes have different structure. We tried to explain this interrelation between the structure and properties for better understanding the main principles of organic chemistry. Nowadays it is very important to make a theoretical part of organic chemistry more powerful. That is why a special attention is being paid to the structure of organic compounds, principles of atomic orbitals formation and types of organic reactions. This guide has a classical structure. Aliphatic hydrocarbons are considered at first, then aromatic hydrocarbons and at last nitrogen and halogen organic compounds. 8
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