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Chemistry 30 Organic Chemistry Notes A. Carbon Compounds 30-C1.1k define organic compounds as compounds containing carbon, recognizing inorganic exceptions such as carbonates, cyanides, carbides and oxides of carbon organic compounds are those in which _______________ atoms are almost always bonded to each other, to __________________ atoms and a few other atoms (___________________) inorganic exceptions are the ___________________________________ __________________________________________________________ (no C-C bonds or C-H bonds) eg) _____________________________________________________ there are ________________ of organic compounds and all contain ___________________________________ carbon is unique for two reasons: a) it can bond with ________________________ atoms to form _________________________________________________ b) it can form combinations of ___________________________ ____________________________ (no other element does this!!!!) recall polarity and intermolecular forces from the chemical bonding unit polar bonds are formed when there is an ________________ pull on e _____________ compounds are formed when the polar bonds within a molecule ______________________________________ each other out the presence of _______________________________ forces and ________________________________________ will allow polar compounds to ________________________________, since it is also polar _________________________ compounds only have LD forces between molecules and _______________________ dissolve in water 30-C1.2s perform an experiment to compare the properties of organic compounds with inorganic compounds, considering properties such as solubility, viscosity, density, conductivity and reactivity Chemistry 30 Organic Chemistry 1 Jill Agnew B. Structural Isomers 30-C1.5k define structural isomerism as compounds having the same empirical formulas, but with different structural formulas, and relate the structures to variations in the properties of the isomers isomers are compounds with the _______________________________ but a ___________________________________ Example 1 Draw the three structural isomers for C5H12. 1. 2. 3. Example 2 Draw three structural isomers for C4H8F2. 1. 2. 3. 30-C1.3s compile and organize data to compare the properties of structural isomers different structures result in different ____________________ the arrangement of the atoms determines the types of intermolecular attractions which then determines properties such as _______________ and ___________________ in water Example Draw two isomers of C3H8O. Which one would have a boiling point of 7.4C and which would have a boiling point of 82.5C? Explain why the boiling points are so different. Chemistry 30 Organic Chemistry 2 Jill Agnew C. Formulas and Structural Diagrams organic molecules can be drawn in three different ways: 1. complete structural diagram – shows _____________________ eg) C3H8 C3H7F 2. condensed structural diagrams – shows ___________________ _______________________ but includes the ______________ etc. attached to each carbon eg) C3H8 C3H7F 3. line structural diagrams – shows only ____________________ ______________________________ bonds eg) C3H8 C5H12 C4H8 Chemistry 30 Organic Chemistry 3 Jill Agnew 30-C1.2s build molecular models depicting the structures of selected organic and inorganic compounds Your Assignment: pg 1 D. Prefixes 1. Number of Functional Groups 6 = hexa 2 = di 7 = hepta 3 = tri 8 = octa 4 = tetra 9 = nona 5 = penta 10 = deca 2. Number of Carbons 1 = __________ 6 = __________ 2 = __________ 7 = __________ 3 = __________ 8 = __________ 4 = __________ 9 = __________ 5 = __________ 10 = __________ 30-C1.2k identify and describe significant organic compounds in daily life, demonstrating generalized knowledge of their origins and applications 30-C1.3k name and draw structural, condensed structural and line diagrams and formulas, using IUPAC nomenclature guidelines, for saturated and unsaturated aliphatic (including cyclic) and aromatic carbon compounds 30-C1.1sts explain how science and technology are developed to meet societal needs and expand human capability 30-C1.2sts explain that science and technology have influenced, and been influenced by, historical development and societal needs 30-C1.3s follow appropriated IUPAC guidelines when writing the names and formulas of organic compounds Chemistry 30 Organic Chemistry 4 Jill Agnew E. Alkanes eg) ________________________________________ hydrocarbons containing _____________________________________ between the carbons ie) they are __________________________ can be _____________ continuous chains, _________________ chains, ___________ structures __________________________ 1. Properties ___________________________________________ in water can be ___________________________________________ depending on number of carbon atoms relatively ______________________ because the ____________ bonds are ___________________________ 2. Uses natural gas, BBQ’s, lighter fluid, gasoline etc good for making plastics, lubricants 3. Naming IUPAC = International Union of Pure and Applied Chemistry i. Continuous Chains __________________________________ eg) H H H H H C C C C H H H H H ii. Branched Chains branches are called ____________ functional group 1 C = __________; 2C = _________; 3 C = __________ etc find the ___________________________________________ and ____________________________ so the branches get the __________ possible numbers Chemistry 30 Organic Chemistry 5 Jill Agnew to name: name the ____________ first (in _______________________ order), including the ________________________________________ where each group is found, then name the ________________________ __________________(parent name) eg) H H H H H H H C C C C C H H CH3 H H H H H H H C C C C C H CH3 CH2 H H H H CH3 H H H H H H C C C C C H H H Try These: H 1. H 2. H CH3 CH3 H H H H H H C C C C C C H CH3 H CH3 H H H H H H H C C C C C H CH2 H H H CH3 H CH3 Chemistry 30 Organic Chemistry 6 Jill Agnew CH3 3. CH3 CH CH2 CH CH3 CH2 CH CH3 CH3 CH3 4. CH3 C CH3 CH2 CH3 C CH3 CH3 Try These Draw the structure for each of the following compounds: 1. 2,2-dimethylpropane 2. 4-ethyl-2,3-dimethylhexane 3. 4-propyloctane 4. 3,5-diethyl-4-methylheptane Your Assignment: pgs 2-3 in workbook Chemistry 30 Organic Chemistry 7 Jill Agnew iii. Cycloalkanes use the ________________________ as the _________________ name __________ + ____________ + _____________ eg) if there are branches, number the carbons in the ring so the branches get the _______________________________________________________ eg) CH2 CH3 CH3 Try These: CH3 1. CH3 2. CH2 CH2 CH2 CH3 CH3 CH3 CH3 3. CH2 CH2 CH2 CH3 CH2 Chemistry 30 Organic Chemistry 8 Jill Agnew 4. 1,2-dimethylcyclopropane 5. 1,1,2,2-tetraethylcyclohexane 6. 3-butyl-1,1,2-trimethylcyclopentane Your Assignment: pg 4 in workbook C. Alkenes eg) __________________________________________ hydrocarbons containing _____________________________________ ie) they are _________________________________ can be _________ continuous chains, ___________________ chains, ___________ structures ______________________________ 1. Properties 30-C1.3s interpret the results of a test to distinguish between a saturated and an unsaturated aliphatic, using aqueous bromine or potassium permanganate solutions ________________________________________ in water ____________________________________ than corresponding alkane because they have _______________________ which makes the ______ forces of attraction _______________________ eg) ethane BP = 88.6C ethene BP = 103.8C ______________________________ than alkanes double bond has _________________ in the same area __________________________________ and __________________ Chemistry 30 Organic Chemistry 9 Jill Agnew ________________________________ diagnostic test: use ________________________________________ ***alkenes _____________________________________________ with these substances causing a noticeable ______________________, alkanes will not Br2(l) A B alkene KMnO4(l) alkane A B alkane alkene **the alkenes will react causing the colour to disappear as the coloured substance is used up in the reaction 2. Uses plastics (PVC) steroids welding torches 3. Naming i. Continuous Chains ________________________________________ number carbons to give the ___________________________ the _________________________________________ the number where the double bond _________________ is to be given as a “ # ” between the prefix and the suffix eg) H H H H C C C H H ‗ Chemistry 30 Organic Chemistry H H C C C H H H H 10 Jill Agnew H H H C C ‗ H H H C C C H H H H C ‗ H H H C C C H H H H H ii. Branched Chains find the longest carbon chain and number it so the _________________ gets the ___________________ number to name: name the _____________ first (in ______________________ order), including the _________________ of the carbon where each is found, then the _________________________ including the ___________________ of the carbon where the double bond starts eg) CH2 ‗ C CH2 CH2 CH2 CH2 CH CH CH CH3 CH3 CH3 CH2 CH3 CH2 CH3 CH3 CH ‗ CH CH2 CH3 Your Assignment: pgs 5-6 in workbook Chemistry 30 Organic Chemistry 11 Jill Agnew iii. Cycloalkenes double bond is always numbered ____________ _______________ get the ____________________ numbering sequence after the ______________________________ __________ + ____________ + _____________ list branches in ______________________________________ with the ______________ of the carbon they are on eg) CH2 CH3 CH3 CH2 CH3 CH3 Your Assignment: pg 7 in workbook Chemistry 30 Organic Chemistry 12 Jill Agnew D. Alkynes eg) ___________________________________ hydrocarbons containing _____________________________________ ie) they are also _________________________________ can be ___________ continuous chains, _________________ chains not plentiful in nature 1. Properties ________________ ___________________________ (more than alkanes and alkenes) ____________ bond has ________ in the same area _________ force of repulsion boiling points are ________________ than corresponding alkanes and alkenes because of their ________________________________ and the ______________ of triple bonds 2. Uses welding torches 3. Naming i. Continuous Chains _______________________________ number carbons to give the _____________________________ the __________________________________________ the number where the triple bond ________________ is to be given as a “ # ” between the prefix and the suffix eg) H H H C C H H C ≡ H H C C ≡ C H Chemistry 30 Organic Chemistry C H H C C H H H H C C H H H H 13 Jill Agnew ii. Branched Chains find the __________________________________________ and number it so the _________________________ gets the lowest number to name: name the ______________ first (in _____________________ order), including the _______________ of the carbon where each is found, then the ___________________________ including the _________________ of the carbon where the triple bond starts eg) CH CH3 CH ≡ C C ≡ CH CH2 CH2 CH2 CH2 CH2 C CH CH CH3 CH2 CH3 CH2 CH2 CH3 CH3 CH3 Your Assignment: pg 8 in workbook Review alkanes – branches, rings – least reactive alkenes – branches, rings alkynes – branches – most reactive all called ___________________________ all ________________ and ___________________________ in water major intermolecular forces are _______ boiling points are _______ E. Aromatics hydrocarbons containing one or more ___________________________ OR all bonds are the __________________________________________ we draw benzene like this: Chemistry 30 Organic Chemistry 14 Jill Agnew 1. Properties _______________________ the benzene ring structure is ________________________ aromatics are characterized by strong aromas 2. Uses ASA, amphetamines, adrenaline, benzocaine (anesthetic) moth balls, TNT wintergreen, menthol, vanilla, cinnamon SPF in sunscreen 3. Naming i. Benzene as a Branch if you have a really long carbon chain, it is easier to call the benzene ring a ____________________________________ eg) CH3 CH2 ‗ CH CH2 CH CH2 CH2 CH C CH2 CH2 CH2 CH2 CH3 CH3 CH3 ii. Benzene as the Main Compound if only one group is attached, give the ___________________________ attached to ________________________________________________ eg) CH3 Chemistry 30 Organic Chemistry 15 Jill Agnew if there is more than one branch, number them so they get the _________________________________________ and name ___________________________________________________ eg) CH3 CH2 CH3 CH3 CH3 CH3 CH2 CH2 ***watch out for this! C2H5 CH3 Your Assignment: pgs 9-10 in workbook 30-C1.4k identify types of compounds from the hydroxyl, carboxyl, ester linkage and halogen functional groups, given the structural formula Chemistry 30 Organic Chemistry 16 Jill Agnew F. Alcohols organic compounds with one or more ____________________ __________________________________ 1. Properties have much ___________________________________________ than corresponding aliphatics because of ___________________________ eg) methane (CH4) BP = _____________ methanol (CH3OH) BP = ______________ _____________ the __________ end of the alcohol is ______________ while the _________________________ end _____________ small alcohols are ________________ in water and large alcohols are _________ 2. Uses antifreeze, rubbing alcohol, beverages, moistening agent 3. Naming number the longest carbon chain containing the __________________ so the ___________ group gets the ____________________________ __________________ name (_________________ at end) + _______ give the __________________________________________ where the _______________________________ is found between the parent name and the suffix if there is _____________________________________ hydroxyl group, use a prefix (_________________________________) to indicate the ___________________ of OH groups and place the numbers between the parent name and the suffix ***Note, if the suffix starts with a vowel, drop the “e” on the parent name; if the suffix starts with a consonant, keep the “e” on the parent name eg) H H H H H C C C C H H OH H Chemistry 30 Organic Chemistry H 17 Jill Agnew H H H CH3 H H C C C C H H OH H H CH3 H H C C C C H OH OH H an unusual case: H H OH Your Assignment: pg 11 in workbook G. Organic Halides where ______ is __________________ and ______ is a ___________ organic compounds where ________________ has been replaced by _______________________________________________________ do not readily occur in nature 1. Properties can be ____________ or _______________________, depending on the placement of the halogen groups many are ________________________________________________ 2. Uses manufactured for human use eg) DDT, PCB, CFC anesthetics dry cleaning fluid plastics, polymers (Teflon) Chemistry 30 Organic Chemistry 18 Jill Agnew 3. Naming same rules as before…name branches (__________________ included now) ___________________________________ F = _____________ Cl = ____________ Br = ____________ I = ____________ eg) H H Cl Cl H C C C C H H H H I H F CH3 Your Assignment: pg 12 in workbook H. Carboxylic Acids where _______ is _______________________ organic compounds containing the ____________________________ _____________________________________ considered __________________ since double bonds in functional groups are not taken into account 1. Properties _____________________________________________________ ________ boiling points due to _____________________________ __________________________________ diagnostic test: use _______________________________ (will turn _________), readily react with ______________________, _________________________________________ 2. Uses recycling rubber – methanoic acid vinegar – ethanoic (acetic) acid rust remover – oxalic acid fruits – citric acid Chemistry 30 Organic Chemistry 19 Jill Agnew 3. Naming count the longest carbon chain including the ______________ in the __________________________ the carbon in the carboxyl group is always number ________ drop ______ and add _________________________ eg) O ║ H C OH O H H ║ C C OH H O ║ C OH O I H H H C C C H H H ║ C OH Your Assignment: pg 13 in workbook I. Esters where _______ can be a carbon chain or hydrogen and ________ can be a carbon chain Chemistry 30 Organic Chemistry 20 Jill Agnew combination of a ______________________________ and an ______________________ considered _____________________ since double bonds in functional groups are not taken into account 1. Properties ________________ _____________ esters ______________________ in water, ____________ esters _________ boiling points slightly lower than corresponding carboxylic acids and alcohols due to lack of hydrogen bonding very _____________ which allows them to generate ____________ 2. Uses flavouring agents 3. Naming identify the _________________ used to make the ester change the alcohol name to the corresponding ___________ name eg) methanol would become _________________ identify the __________________________ the ester was made from drop the “oic acid” and replace with _________________ eg) butanoic acid would become __________________________ put the ______________________ together with a ______________ in between eg) ______________________________________ you can have __________________ on esters…they follow the alphabetical rule, numbering begins at the _________________ of the alcohol and the C=O end of the carboxylic acid eg) O H H H H C C C H H H H H C C ║ C O H H C C H H H O H ║ C H HChemistry Chemistry 30 Organic O H CH3 C C H H21 H Jill Agnew O H H H C C ║ C O CH3 CH3 H H C C H H H Your Assignment: pg 14 in workbook J. Boiling Points and Solubility 30-C1.6k compare, both within a homologous series and among compounds with different functional groups, the boiling points and solubility of examples of aliphatics, aromatics, alcohols and carboxylic acids we can compare the boiling points of various organic compounds using their _________________ and the _______________________ ______________________________ between the molecules Example 1 Put the following organic compounds in order from highest boiling point to lowest boiling point. alcohol, alkane, alkene, aromatic, carboxylic acid Example 2 Put the following homologous series of organic compounds in order from highest boiling point to lowest boiling point. C2H6, C2H5OH, CH3COOH, C2H4 Chemistry 30 Organic Chemistry 22 Jill Agnew we can also compare the ____________________ of various organic compounds using their polarity Insoluble Organic Compounds Soluble Organic Compounds K. Organic Reactions 30-C2.1k define, illustrate and provide examples of simple addition, substitution, elimination, esterification and combustion reactions 30-C2.2k predict products and write and interpret balanced equations for the above reactions 30-C2.4k relate the reactions described above to major reactions that produce thermal energy and economically important compounds from fossil fuels 30-C2.3s use IUPAC conventions when writing organic chemical reactions 1. Combustion Reactions occurs when a _______________________ reacts with ___________ products are always ________________________________________ ________________________________________________ these are economically important reactions for they are the major reactions that produce __________________________________ required for fuelling our vehicles, heating our homes, and producing electricity ___ C5H12(l) + ___ O2(g) eg) H H H H H C C C C H H H H H Chemistry 30 Organic Chemistry + ____ O2(g) 23 Jill Agnew 2. Addition Reactions a ____________ or _____________ bond in an alkene or alkyne is ___________________ and a group or element is ___________ eg) H H ‗ C H H H H ‗ C H H H H ‗ H H H H ‗ C H + H OH + H H + H Br + 1 Cl2 cat C H H Cl cat C C Cl cat C C + cat C H C cat ≡ C ≡ H cat C H + 2 Cl2 Try These: 1. H C H ‗ H H H C C C cat H + ChemistryH30 Organic Chemistry H Br2 24 Jill Agnew 2. H H H C C ‗ H H H C C C H H H H + cat HCl 3. H H C H C ≡ C C H H + cat 1 Cl2 H Your Assignment: pg 15 3. Substitution Reactions the replacement (_____________________) of a hydrogen on an alkane or aromatic with __________________________________ (eg. F, Cl etc) commonly used to make ____________________________________ Examples: H 1. + H C Cl – Cl cat H H 2. 3. Br – Br + + Chemistry 30 Organic Chemistry I–I cat cat 25 Jill Agnew 4. H H H H H C C C C H H H H + H cat Br2 4. Esterification Reactions the reaction of a ________________________________ with an ________________________ the catalyst is ____________________________________ Examples: 1. O H ║ H H2SO4(aq) C OH + HO C H H 2. O H H H C C H H ║ C H H C C H H H2SO4(aq) OH + HO H 5. Elimination Reactions an ______________ has water removed, forming and ___________ plus the _______________ _________________________________ can react with a _________________________________________ to produce an _______________, a ________________________ and ___________ Examples: 1. H H C C cat H OH H H Chemistry 30 Organic Chemistry 26 Jill Agnew 2. H H H H C C C C OH H H H H H C C H H cat H 3. H H Cl + OH cat Your Assignment: pgs 16-17 6. Polymerization Reactions 30-C1.2sts explain that science and technology have influenced, and been influenced by, historical development and societal needs 30-C2.3k define, illustrate and provide examples of monomers, polymers and polymerization in living systems and nonliving systems 30-C2.3s draw or use models to illustrate polymers a ___________________ is a ______________________________ that forms the _____________________ for a polymer a ______________________ is a _____________________________ formed by the _______________________________________ of ___________________________________________________ depending on the polymer, the monomers that make it up can be _________________________ or _____________________ polymers can be _______________________ eg) _____________________________________________________ polymers can be ____________________ eg) _____________________________________________________ polymers that can be heated and molded into specific shapes are commonly called _____________________ Chemistry 30 Organic Chemistry 27 Jill Agnew plastics are one type of synthetic compound that has been of great benefit to society (although there are also problems associated with then) the names of polymers are the monomer name with _____________ in front many have classical names instead of IUPAC names Addition Polymers formed when the electrons in double or triple bonds in the monomer units are rearranged the polymer is the _________________________________ formed Examples: 1. H H C H ‗ C H + C ‗ cat C H H H H F F F F 2. C ‗ C + C ‗ cat C F F F F H Cl H Cl 3. C 4. ‗ C + H C H H cat C H H C ‗ ‗ C H H + H H C ‗ cat C H Condensation Polymers polymerization reactions that involve the formation of a ___________ Chemistry 30 Organic Chemistry 28 Jill Agnew ___________________ (commonly ____________) as well as the ____________________ each monomer must have ________ functional groups two common linkages formed: 1. _____________ linkage – between carboxyl group (COOH) and hydroxyl group (OH) 2. ______________ linkage – between amino group (NH2) and carboxyl group (COOH) Examples: 1. HO O O ║ ║ C C H H C C H H O H H ║ C C N cat OH + HO OH 2. HO O H H ║ C C N H + HO H Chemistry 30 Organic Chemistry cat H H 29 Jill Agnew K. Petroleum Refining 30-C1.7k describe, in general terms, the physical, chemical and technological processes used to separate organic compounds from natural mixtures or solutions 30-C2.1sts explain how science and technology are developed to meet societal needs and expand human capability Alberta has vast reserves of petroleum in the form of natural gas, crude oil and oil sand deposits most of this petroleum is refined and then burned as _________ petrochemicals, basic hydrocarbon raw materials such as ethane and propene, are also used in the production of ______________ refining of petroleum separates the crude mixture into purified components ________________________________________________ is used to separate the components distillation works because of the different ______________________ of the components of petroleum the ________________ the molecule and the _______________ the boiling point, the ____________________ it rises in the tower (asphalt, fuel oil, wax at bottom; gasoline at top) there are two types of reactions in petroleum refining: 1. Cracking __________ long chain hydrocarbons into ______________________ cracking requires heat and pressure there are many different types of cracking reactions, forming different products (alkanes, alkenes) eg) catalytic cracking, steam cracking, hydrocracking hydrocracking requires ________ Examples: 1. cat C9H20 + C8H18 2. cat Chemistry 30 Organic Chemistry 30 CH3 CH2 CH2 CH3 + CH3 Jill Agnew CH2 CH3 O ║H 2. Reforming small hydrocarbons are _______________ to make _____________________________________ requires heat and pressure there are several types of reforming reactions eg) alkylation to produce “high octane” gasoline all reforming reactions produce _________ Examples: 1. C7H16 + C12H26 2. ethane + octane cat cat 30-C1.1s design a procedure to separate a mixture of organic compounds, based on boiling point differences Your Assignment: pgs 18-19 Separate an Organic Mixture – pg 581 Organic Reactions and the Environment Assignment Chemistry 30 Organic Chemistry 31 Jill Agnew