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LS Chem 30: Organic Chemistry Inorganic Carbon Compounds: isomers: a set of compounds that have the same molecular formula but different structural formula EX. C6H14 has different isomers Representing Organic Compounds 1. Empirical molecular formula 2. Expanded molecular formula 3. Structural diagram 4. Condensed structural diagram 5. Line structural diagram EX. C7H16. Write out a condensed structural diagram and a line structural diagram for 2 isomers. EX. C5H10. Write out a condensed structural diagram and a line structural diagram for 3 of these isomers. Alkanes The general formula of alkanes: Alkanes form a homologous series. They are _______________ in water. Naming Alkanes The IUPAC name of any organic compound has three basic parts: prefix + root + suffix EX. Heptane EX. Decane side groups: methyl, ethyl, propyl, butyl…. If there is more than one type of side group, they are named in alphabetical order. If there is more than one of the same type of side group, a prefix indicating the number of that type of side group is included. When determining alphabetical order, ignore the prefixes di-, tri-, tetra-, etc. EX. Name the following compounds. Drawing Alkanes **Fill in the hydrogens so that each carbon has enough bonds. EX. Draw a structural diagram for _____________________ EX. Draw a structural diagram for __________________________ Alkenes Alkenes are __________________________hydrocarbons =_____________________ Alkenes __________________ in water The general formula of alkenes: prefix + root + suffix suffix: The suffix for alkenes is “-__________________”. EX. Name/Draw the following compounds Alkynes Alkynes are _________________________________hydrocarbons = _________________ The general formula of alkynes: Alkynes have the same naming rules as alkenes except the suffix ends in –______ Alkynes _______________ in water and their linear structure around the triple bond causes them to attract one another more strongly = ____________ boiling point EX. Name/Draw the following compounds Cyclic Hydrocarbons _____________________ hydrocarbon rings. Naming Cyclic Hydrocarbons: Root = the ring Suffix = single double or triple bonds? *Assume the double or triple bond is carbon 1 Prefix = side chains Drawing Cyclic Hydrocarbons: Ring = line structural diagram Side chains = condensed structural diagrams EX. Name the following compounds EX. Draw the structure of __________________ Aromatic Hydrocarbons are characterized by the presence of the benzene ring. Naming Aromatic Hydrocarbons The root name for the molecule is –____________________ The carbons are numbered to locate the side chains (if more than one). EX. Name the following compound EX. Draw the structure of __________________________________________ If a chain is bigger than the ring, benzene is a __________________ side group. EX. Name the following compound EX. Draw the structure of _____________________________________ Hydrocarbon Derivatives A functional group is a special arrangement of atoms that is mainly responsible for the chemical behaviour of the molecule. Alcohols: Alkanes: Alkenes: Alkynes: Alkyl Halide: Carboxylic Acid: Ester: Alcohols contains the __________(-OH) functional group. Naming and Drawing Alcohols: Identify the root: Locate the longest chain that includes the hydroxyl group. Identify the suffix: -ol Identify the prefix EX. Name the following compounds EX. Draw the structure of _____________________________________ Physical Properties of Alcohols -OH group is POLAR = _______________in water, decreasing with molecule size _________________ boiling points than alkanes of same size Alkyl Halides contains at least one halogen (Group 17) atom. Naming and Drawing Alkyl Halides: Identify the root Identify the prefix: Name and number any alkyl side groups. Insert the number(s) of the carbon atom(s) bonded to the halogen(s). Use the prefix(es) that identify the specific halogen(s) (________________________________________________________________) EX. Name the following compounds EX. Draw the structure of _____________________________ Carboxylic Acids weak acids that contain the carboxyl group (-COOH), which is polar o = _______________boiling points o = _______________ in water; decreasing with molecule size o = turn litmus _________________ Naming and Drawing Carboxylic Acids: Identify the root Identify the suffix: Drop the –e at the end of the name of the parent alkane and replace it with –oic aicd Identify the prefix: The carbon atom of the carboxyl group is always number one. Ecreasing with molecule EX. Name the following compounds EX. Draw the structure of _________________________ Esters functional group: boiling point is ___________ compared to alcohols or acids have aromas formed by a reaction between a ____________ and an _______________. O O + R C O H carboxylic acid + H O R’ alcohol R C O R’ ester H O H water Naming and Drawing Esters: Identify the root: ________________ group. The root of the name of the ester is based on the name of the acid. Determine the name of the parent acid. Identify the suffix: Remove the –oic acid from the name of the parent acid and replace it with –________. Identify the prefix: The name of the alkyl group originating from the alcohol is the prefix for the name of the ester. EX. Name the following compounds EX. Draw the structure of _____________________________ Organic Reactions Combustion In a _____________ combustion reaction, a hydrocarbon reacts with oxygen to produce carbon dioxide, water vapour and energy. When fuels are burned with insufficient oxygen, _________________ combustion takes place. In these reactions, carbon monoxide (CO(g)) and even carbon soot (C(s)) can be produced. Addition Reactions ________________ hydrocarbons The addition of hydrogen produces an ____________: EX. pent-2-ene + hydrogen The addition of a halogen produces an alkyl halide: EX. cyclohexene + fluorine A simple addition reaction using Br2 (aq) is used to _________________________________ Ex. The reaction between but-2-ene and bromine vs butane and bromine The addition of a hydrogen halide also produces an alkyl halide Because non-identical atoms are being added in, 2 different isomers may be formed. EX. but-2-yne + hydrogen bromide The addition of water produces an alcohol. Isomers may also be produced. EX. hex-1-ene + water Elimination Reactions a ____________ bond is formed Alcohols can be converted into ______________ when they are heated up in the presence of a ____________________ (H2SO4(aq)) catalyst. EX. . H2SO4 pentan-2-ol Alkyl halides can be converted into alkenes when they are heated up in the presence of a ______________________, such as sodium ethoxide (NaOCH2CH3). EX. Bromopropane NaOCH2CH3 Isomers can also be produced by elimination reactions, if the double bond can form at alternate locations. EX. 2-chlorobutane + sodium ethoxide Substitution Reactions a __________________ hydrocarbon reacts with a halogen (X2). They require the energy from ___________________________ to take place more quickly. EX. UV butane + chlorine EX. UV benzene + fluorine Esterification Reactions the reaction between an alcohol and a carboxylic acid. Water is also produced. require a _____________________ (H2SO4) catalyst. EX. H2SO4 propanoic acid + ethanol Addition Polymerization Alkene monomers can be linked together through multiple addition reactions to form a polymer. The polymer is the only product. Condensation Polymerization Monomers are combined through multiple condensation reactions. A second smaller product, usually water, is also produced. Each monomer must have two functional groups, usually one at each end of the molecule. PRACTICE For each of the following chemical reactions, write out a structural diagram, name all products, and identify the reaction type. 2-methylbut-1-ene + bromine cyclobutyne + oxygen 2,3-dimethylprop-1-ene + hydrogen chloride cyclobutene + chlorine butane + fluorine UV H2SO4 2-methlypropanoic acid + methanol benzene + oxygen 2-chloroheptane + sodium ethoxide cyclobutane + chlorine UV H2SO4 2-methylbutan-1-ol + ethanoic acid 2-bromohex-1-yne + hydrogen H2SO4 3-ethylcyclohexanol Refining Petroleum _______________________________ is the first step in refining petroleum. The different boiling points of the hydrocarbons allow them to be separated into different fractions. The boiling point of a hydrocarbon increases as the molecular size increases (greater London forces). The smallest hydrocarbons are captured at the top of the tower and larger hydrocarbons are collected closer to the bottom. __________________ converts larger hydrocarbons into smaller hydrocarbons. __________________cracking involves the heating of a hydrocarbon under pressure in the absence of air. This breaks carbon-carbon bonds. Steam at more than 800oC is often used as the heat source. ___________________cracking is a low pressure process that passes a powdered catalyst through heavy hydrocarbon fractions at 600oC. ___________________ involves the addition of hydrogen gas during a catalytic cracking process. _________________ uses heat, pressure and catalysts to convert straight-chain alkanes into branched-chain alkanes, cyclic alkanes and aromatics. ___________________ is a reforming process in which smaller hydrocarbons are chemically joined together to make a larger, more branched hydrocarbon.