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Study Guide CHEM12U SG.indd 1 11-11-11 10:37 AM Unit Organic Chemistry 1 Chapter 1: Organic Compounds Organic chemistry is the study of carbon-containing compounds and their properties. There are a few carbon compounds, including carbon oxides and carbonates that we consider to be inorganic. Understanding how carbon atoms bond to each other and to other atoms helps explain why organic compounds enable life to exist on Earth. Alkanes are saturated hydrocarbons in which the atoms of carbon are bonded to each other by single bonds. Alkenes and alkynes are unsaturated hydrocarbons with multiple bonds, and they are more reactive than alkanes. They may participate in addition reactions, including hydrogenation, halogenation, hydrohalogenation, and hydration. A naming scheme has been established by the International Union of Pure and Applied Chemistry (IUPAC) to name the organic compounds. Structural isomers are compounds that have the same molecular formula but different molecular geometry. Cis and trans isomers are compounds that are identical except for the position of groups on either side of a double bond. Aromatic hydrocarbons are a class of cyclic unsaturated hydrocarbons that have a ring structure and bonding that causes them to be chemically stable. Other major classes of organic compounds include alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, and amides. Their properties and reactions are determined by their structures and specific functional groups. Big ideas • Organic compounds have predictable chemical and physical properties determined by their respective structures. • Organic chemical reactions and their applications have significant implications for society, human health, and the environment. Chapter 2: Polymers Many of the objects that we use today are made of plastic, at least in part. Plastics are synthetic polymers. Other polymers occur naturally. Silk, spiderwebs, hair, muscle, cotton, and wood are all composed of polymers made by living organisms. Polymers are large molecules—natural or synthetic—made up of many monomers linked together. Homopolymers are polymers made of only a single type of monomer. Copolymers are polymers made of two or more types of monomers. Addition polymers form when monomers link during addition reactions. Condensation polymers are polymers formed when monomers join during condensation reactions. The properties of addition polymers can be varied by selecting monomers with certain substituent atoms or groups. Polyesters are formed by condensation reactions between carboxylic acids and alcohols that result in ester linkages. Polyamides are formed by condensation reactions between carboxylic acids and amines that result in amide linkages. Starch, cellulose, and glycogen are polymers of glucose. Proteins and nucleic acids are condensation polymers. The shape of a protein molecule depends on intermolecular and intramolecular forces. DNA stores information for amino acid sequences, enabling the cell to assemble proteins. Disposal of used plastics has been a serious environmental problem. Many plastics cannot be recycled. The most effective solution is to reduce the quantity of waste produced. NEL SciSG_Che_Ch01.indd 1 Unit 1 • Overview 1 2/24/12 6:33 PM 1.1 Textbook pp. 8–17 Alkanes Vocabulary organic compound cyclic alkane structural isomer hydrocarbon alkyl group complete combustion saturated hydrocarbon substituent group alkyl halide alkane MAIN IDEA: Hydrocarbons contain hydrogen and carbon. In a saturated hydrocarbon, the atoms of carbon are bonded to each other by single bonds. Structural isomers are compounds that have the same molecular formula but different molecular geometry. Alkanes may have a straight-chain structure or a ring structure. Substituent groups may be attached to the parent structure. Alkyl halides are alkanes in which halogen atoms have substituted for one or more hydrogen atoms. 1. Name two alkanes that are used as fuels to heat homes and solder torches. K/U Learning Tip Line Diagrams In a line diagram, imagine that there is a carbon atom at the end of every line and at the intersection of every line. Each one is surrounded by the maximum number of hydrogen atoms. 2. Name and describe three common ways of depicting the structures of organic compounds. K/U 3. Indicate whether each of the following statements is true or false. If you think a statement is false, rewrite it to make it true. K/U (a) A substituent group is any atom or group that replaces carbon in an organic molecule. (b) A structural isomer is a compound that has the same molecular formula as another compound, but a different structure. Learning Tip Memory Aid: Table of Terms You might find it helpful to create a 3-column table summarizing the naming of alkanes with 1 to 10 carbon atoms. List the unbranched straight-chain alkanes, the unbranched cycloalkanes, and the alkyl groups. 2 Unit 1 • Organic Chemistry SciSG_Che_Ch01.indd 2 4. An alkyl group consisting of a 3-carbon chain and 7 hydrogen atoms is called a(n) _________ group. K/U 5. Which of the following is not a saturated hydrocarbon? (a) 1,3-dichlorobutane (b) 2,4-dimethylpentane (c) 2,3,4-trimethyloctane (d) 1,4-diethylcyclohexane K/U NEL 2/24/12 6:33 PM 6. Write the name of each of the following compounds. (a) CH3 CH2 CH CH2 CH2 CH3 (d) CH3 K/U T/I CH3 CH3 CH CH CH3 Cl (b) CH3 CH CH3 CH2 CH2 CH (e) CH3 CH3 C01-F01-OC12USG.ai (c) CH3 CH2 CH3 CH CH CH2 CH2 CH3 (f) CH CH2 C01-F04-OC12USG.ai CH3 CH3 C01-F02-OC12USG.ai C01-F05-OC12USG.ai 7. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: Cyclohexane contains 6 carbon atoms with each carbon atom bonded to 4 atoms, so one molecule of cyclohexane contains a K/U total of atoms. Biology 1224 Study Guide y Guide 0176520848 C01-F01-OC12USG.ai Figure Number C01-F04-OC12USG.ai MPS C01-F03-OC12USG.ai Company MPS K/U 8. Which of the following is a property of alkanes? C01-F06-OC12USG.ai Technical 1st pass (a) The combustion reactions are endothermic. Pass 1st pass (b) The molecules are polar and form hydrogen bonding. Approved (c) The boiling point decreases with the length of the carbon chain. Not(d) Approved Van der Waal forces are the main intermolecular forces between y Guide Biology 12 Study Guide molecules. 0176520848 C01-F02-OC12USG.ai Figure Number MPS Company C01-F05-OC12USG.ai MPS Technical 1st pass Pass 1st pass Approved Not Approved dy Guide Biology 12 Study Guide 0176520848 C01-F03-OC12USG.ai Figure Number MPS Company 1st pass C01-F06-OC12USG.ai MPS Technical NEL Pass 1.1 Alkanes 3 1st pass Approved Not Approved SciSG_Che_Ch01.indd 3 2/24/12 6:33 PM Learning Tip Molecular Formulas To obtain the molecular formula, start with the base formula for straightchain alkanes, CnH2n12, or that for cycloalkanes, CnH2n. Subtract the number of hydrogen atoms that have been replaced by substituent groups and add the substituent groups. For example, 1,2-dimethyl cyclobutane has the base formula C4H8 for cyclobutane with two H atoms replaced by two CH3 groups. Number of H atoms 5 8 2 2 1 6 5 12 Number of C atoms 5 4 1 2 5 6 The molecular formula is C6H12. 9. Draw a structural formula and write the molecular formula for each of the following compounds. T/I C (a) 3-ethyl-4-methylhexane (b) 1-bromo-3-ethylcyclohexane (c) 4-propan-2-yloctane 10. Draw and name three structural isomers that have the molecular formula C5H12. T/I C 4 Unit 1 • Organic Chemistry SciSG_Che_Ch01.indd 4 NEL 2/24/12 6:33 PM 1.2 Alkenes and Alkynes Vocabulary unsaturated hydrocarbon stereoisomer functional group alkene cis isomer addition reaction alkyne trans isomer Markovnikov’s rule Textbook pp. 18–27 aliphatic hydrocarbon MAIN IDEA: An alkene is a hydrocarbon that has at least one double bond between two carbon atoms. The carbon chain is numbered using the lowest number for the double bond. The root name ends in -ene. An alkyne is a hydrocarbon that has at least one triple bond between two carbon atoms. Naming alkynes is similar to naming alkenes. The root name ends in -yne. Cis and trans isomers are compounds that are identical except for the positions of groups on either side of a double bond. In cis isomers, the groups are located on the same side of the double bond. In trans isomers, the groups are located on the opposite sides of the double bond. 1. Indicate whether each of the following statements is true or false. If you think a statement is false, rewrite it to make it true. K/U (a) Each molecule of a hydrocarbon containing carbon–carbon double or triple bonds contains fewer than the maximum number of hydrogen atoms. (b) Other than the use of cis and trans to describe the positions of the groups around the double bond, stereoisomers have the same molecular formula and chemical name. (c) cis-hex-2-ene and trans-hex-3-ene are stereoisomers. 2. Name the following compounds. (a) CH2 CH3 CH CH C K/U T/I CH3 (c) H3C CH2 Br (b) CH 3 CH3 (d) CH2 C C C CH2 CH3 Cl NEL SciSG_Che_Ch01.indd 5 C01-F07-OC12USG.ai C01-F09-OC12USG.ai 1.2 Alkenes and Alkynes 5 2/24/12 6:33 PM 3. Draw the structures of the following compounds. (a) 3-methylhexa-1,3-diene T/I C (b) 5-ethyl-2-methylhept-3-yne (c) 1-ethylcyclobut-1-ene 4. Match the condensed formula on the left with the possible alkene or alkyne on the right. K/U T/I (a) CH3CH2CCCH2CH3 (b) CH3CH2CH2CH2CCH (c) CH3CHCHCHCHCH3 (d) CH3CH2CHCHCH2CH3 6 Unit 1 • Organic Chemistry SciSG_Che_Ch01.indd 6 (i) hex-3-ene (ii) hex-2,4-diene (iii) hex-1-yne (iv) hex-3-yne NEL 2/24/12 6:33 PM 5. An aliphatic hydrocarbon has molecular formula C5H10. T/I C (a) Draw all possible non-cyclic structural isomers of the compound. Write the name of each structure. Learning Tip Remembering Cis and Trans To use cis and trans correctly, you could think of cis as being like sisters: side by side. And trans means “across,” as in transatlantic. Learning Tip (b) Identify if any of the structures in part (a) have stereoisomers. Draw and name the cis and trans isomers of the compound. 6. Draw the cis and trans isomers of the following compounds. (a) 3-chlorohex-3-ene K/U Stereoisomers vs. Structural Isomers Structural isomers have the same molecular formula—the same numbers and types of atoms, but with the atoms bonded in different ways. Stereoisomers are identical in their structural formulas, but the arrangement of the atoms or groups in space around two carbon atoms do not allow these atoms or groups to be rotated to change from one isomer to the other. Cis/trans isomers are common for alkenes, as their molecules cannot rotate around the double bond. C (b) 1,2-dimethylcyclobut-1-ene NEL SciSG_Che_Ch01.indd 7 1.2 Alkenes and Alkynes 7 2/24/12 6:33 PM MAIN IDEA: Hydrocarbons with multiple bonds are more reactive than alkanes and participate in addition reactions in which atoms from one molecule are added to another molecule. Addition reactions include hydrogenation, halogenation, hydrohalogenation, and hydration. Markovnikov’s rule states that, when two non-identical entities are added at a double bond, the major product will be formed by the hydrogen atom bonding to the carbon atom with more hydrogen atoms attached. 7. A __________________ group is a specific group of atoms within a molecule that affects the properties of the compound such as the chemical reactivity with other elements or compounds. K/U 8. Which of the following is not true for the addition reactions of alkenes or alkynes with water? T/I (a) The double-bonded or triple-bonded carbon atoms take part in the reaction. (b) The alkene or alkyne gains atoms but does not lose any atoms. (c) There is only one product resulting from the reaction. (d) Two molecules react to form one molecule. 9. Draw the structure of the product of each of the following reactions. Write the IUPAC names of the reactant and the product, and identify the type of addition reaction. Apply Markovnikov’s rule if needed. T/I C (a) CH3 CH3 C CH CH3 H2 CH3 Br2 (b) C01-F11-OC12USG.ai CH3 (c) CH3 C CH CH CH3 HCI CH3 C01-F12-OC12USG.ai CH2 (d) CH3 CH2 C CH2 CH3 H2O Biology 12 Study Guide 0176520848 Figure Number Company C01-F11-OC12USG.ai MPS Technical 8 Unit 1 • Organic Chemistry Pass 1st pass C01-F13-OC12USG.ai NEL Approved Biology 12 Study Guide Not Approved 0176520848 SciSG_Che_Ch01.indd 8 2/24/12 6:34 PM 1.3 Aromatic Hydrocarbons Vocabulary aromatic hydrocarbon Textbook pp. 28–31 phenyl group MAIN IDEA: Aromatic hydrocarbons are a class of cyclic unsaturated hydrocarbons that have a ring structure and bonding that causes them to be chemically stable. Measurements show that the bonds in a benzene ring are all equal in length. 1. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: The commercial use of benzene has discontinued because benzene contains caffeine. K/U 2. The structural diagram of benzene shows that a benzene molecule has three double bonds and three single bonds. K/U C (a) Experiments indicate that all six bonds are equal in length. Explain how this can occur. (b) Draw a common representation of benzene. 3. (a) Name a commercial solvent that has replaced benzene as a solvent used in C01-F15-OC12USG.ai industrial processes and for dry-cleaning clothes. (b) Draw the structure of the compound and write its IUPAC name. K/U C OC12USG.ai NEL SciSG_Che_Ch01.indd 9 1.3 Aromatic Hydrocarbons 9 2/24/12 6:34 PM 4. Name the following compounds. (a) CH3 K/U (c) CH3 CH2CH CH2 Br (b) Cl H3C Learning Tip Traditional Names for Aromatic Hydrocarbons An older naming convention for substituted aromatic compounds used the Greek prefixes ortho–, meta–, and para– to indicate the positions of substituents. Ortho substituents are on adjacent carbon atoms in 1,2 positions. Meta substituents are separated by 1 carbon atom in 1,3 positions. Para substituents are located on opposite sides of the 6-carbon ring in 1,4 positions. CH2CH3 5. Draw a structural formula to represent each of the following compounds. C01-F18-OC12USG.ai (a)C01-F16-OC12USG.ai metadiethylbenzene K/U C (b) 5-chloro-7-phenyloct-1-yne C01-F17-OC12USG.ai Biology 12 Study Guide MAIN IDEA: Benzene is less reactive than alkenes but more reactive than alkanes. Since it participates in substitution reactions, benzene behaves more like an alkane. 0176520848 Figure Number C01-F18-OC12USG.ai Learning Tip 6. Which of the following compound is the least reactive? T/I Figure Number C01-F16-OC12USG.ai Company MPS Reactivity of Hydrocarbons (a) benzene Company MPS Technical In general, saturated hydrocarbons (b) hex-1-yne 1st pass Technicalare more stable than unsaturated Pass (c) hex-1-ene Pass 1st pass hydrocarbons. Compared to Approved (d) hexane unsaturated hydrocarbons, each Approved Not Approved bond in benzene is identical and 7. Draw the chemical equation for the following reactions. Include the names of Not Approved these bonds are much more stable the organic reactant and product. T/I C Biology 12 Study Guide than a carbon–carbon double bond. (a) hydrogenation of benzene 0176520848 Biology 12 Study Guide 0176520848 Therefore, aromatic compounds are Figure muchNumber less reactive thanC01-F17-OC12USG.ai alkenes but Company MPS more reactive than alkanes. Technical Pass 1st pass Approved (b) substitution reaction of benzene using hydrochloric acid, HCl(aq) Not Approved 10 Unit 1 • Organic Chemistry SciSG_Che_Ch01.indd 10 NEL 2/24/12 6:34 PM 1.4 Alcohols, Ethers, and Thiols Vocabulary Textbook pp. 32–39 alcohol tertiary alcohol ether primary alcohol hydrogen bonding condensation reaction secondary alcohol dehydration reaction thiol MAIN IDEA: Alcohols contain a hydroxyl group, –OH. The hydroxyl group allows alcohols to form hydrogen bonds. Alcohols can be further classified as primary, secondary, and tertiary. 1. What are two reactions that can be used for the commercial preparation of ethanol? K/U 2. Since the electronegativity difference between carbon and hydrogen is _______________ than that between carbon and oxygen, the C—H bond is _______________ polar than the C—O bond. Also, the bond between carbon and _______________ is polar, so alcohol molecules are polar. K/U 3. Match each alcohol on the left with the description and use on the right. (a) ethanol (b) propan-1-ol (c) propan-2-ol (d) ethane-1,2-diol (e) propane-1,2,3-triol K/U (i)polyalcohol with three –OH groups used in pharmaceutical preparations to help dissolve less polar compounds (ii)primary alcohol used as a solvent for lacquers and waxes, and as brake fluid (iii)polyalcohol with two –OH groups used as antifreeze in automobile engines (iv)secondary alcohol used as an antiseptic to clean the skin before injections (v) primary alcohol used in alcoholic beverages 4. Indicate whether each of the following statements is true or false. If you think a statement is false, rewrite it to make it true. K/U (a) The simplest aromatic alcohol has one hydroxyl group bonded to cyclohexane. Learning Tip Classifying Alcohols Alcohols are classified according to the number of other carbon atoms that are directly bonded to the carbon atom attached to the hydroxyl group, –OH. A primary alcohol has the –OH group attached to the carbon atom at the end of the carbon chain, which has only 1 carbon atom attached to it. A secondary alcohol has the –OH group bonded to a carbon atom that is attached to 2 other carbon atoms. A tertiary alcohol has the –OH group bonded to a carbon atom that is attached to 3 other carbon atoms. (b) As the size of the carbon chain of a simple alcohol grows, the alcohol becomes less soluble in water because the hydrocarbon region of an alcohol molecule is non-polar. 5. Which of the following compound is a tertiary alcohol? T/I (a) 2,4-dimethylpentan-3-ol (c) 4-methylheptan-3-ol (b) 3-ethylhexan-3-ol (d) 3,5-diethyloctan-4-ol NEL SciSG_Che_Ch01.indd 11 1.4 Alcohols, Ethers, and Thiols 11 2/24/12 6:34 PM 6. Write the name of each of the following compounds. CH3 (a) H2C CH CH2 CH2 CH CH2 CH2 CH3 CH2 K/U (c) CH3 OH CH2 CH3 CH2 CH2 OH (d) H3C (b) OH OH CH CH CH OH OH OH C01-F19-OC12USG.ai 7. Draw a structural formula for each of the following compounds. K/U C C01-F21-OC12USG.ai (a) 3-methylpentane-2,4-diol C01-F22-OC12USG.ai C01-F20-OC12USG.ai (b) 5-bromo-3-ethylhexan-2-ol Biology 12 Study Guide Biology 12 Study Guide 0176520848 Figure Number C01-F19-OC12USG.ai Company MPS Technical Pass 0176520848 Figure Number C01-F21-OC12USG.ai Company MPS (c) 3-chloro-2-methylcyclohexanol Technical 1st pass Pass Approved 1st pass Approved Not Approved Not Approved Biology 12 Study Guide Biology 12 Study Guide 0176520848 0176520848 Figure Number Company C01-F20-OC12USG.ai MPS Technical Pass 1st pass Figure Number Company Pass Approved Not Approved Not Approved SciSG_Che_Ch01.indd 12 MPS 8.Technical Explain why methanol has a higher boiling point than methane. Approved 12 Unit 1 • Organic Chemistry C01-F22-OC12USG.ai K/U T/I 1st pass NEL 2/24/12 6:34 PM MAIN IDEA: Alcohols can be produced by hydration reactions of alkenes. Dehydration reactions use a catalyst and acid to change the alcohol back to an alkene and water. In a combustion reaction an alcohol reacts with oxygen, producing carbon dioxide and water. 9. Write a chemical equation for each of the following reactions. Classify the reaction type. K/U T/I C (a) butan-2-ol from but-2-ene (b) but-1-ene from butan-1-ol (c) water and carbon dioxide from ethanol (d) methoxybutane from butan-1-ol and methanol MAIN IDEA: Ethers can be produced from the condensation reaction of alcohols. Ethers are widely used as solvents because of their ability to dissolve both polar and non-polar substances. Thiols contain the sulfhydryl functional group, –SH. They typically have strong odours and react similarly to alcohols. 10. Ethoxyethane is an effective anesthetic that has been used successfully for decades. Why is it being replaced? What is the current major use of this compound? K/U 11. Which of the following is not true of thiols? K/U (a) Thiols generally have strong odours. (b) Gas delivery companies add thiols to natural gas to detect leaks. (c) Hydrogen peroxide reacts with thiols to form disulfide compounds with a strong odour. (d) The reaction of thiol is similar to that of alcohols as the sulfhydryl group, –SH, is similar to the hydroxy group, –OH. NEL SciSG_Che_Ch01.indd 13 1.4 Alcohols, Ethers, and Thiols 13 2/24/12 6:34 PM 1.5 Textbook pp. 40–46 Aldehydes and Ketones Vocabulary carbonyl group aldehyde ketone MAIN IDEA: If a carbonyl group (C w O) is attached to at least 1 hydrogen atom, the molecule is an aldehyde. It is named using the suffix –al. If a carbonyl group is attached to 2 carbon atoms, the molecule is a ketone. It is named using the suffix –one. The carbonyl group makes organic molecules polar, giving them higher boiling points and greater water solubility than the corresponding alkanes. 1. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: In an aldehyde other than methanal, the carbonyl group is bonded to only one hydrogen atom. K/U Study Tip Naming Aldehydes and Ketones When numbering the atoms in an aldehyde or a ketone, the carbonyl (C w O) functional group takes precedence over other substituents, such as alky groups, halogen atoms, and a hydroxyl groups. 2. Name each of the following aldehydes and ketones. (a) (c) CH3 CH3 CH2 CH CH3 (b) C O CH2 CH CH CH3 Br (d) CH3 CH3 K/U C O OH O H (e) CHC01-F23-OC12USG.ai 3CH2CH(CH3)CH2CHO O C01-F25-OC12USG.ai (f) CH3C(Cl)2CH2COCH3 3. Draw a structural formula for each of the following compounds. (a) 2,2-dimethylpropanal C01-F24-OC12USG.ai K/U C C01-F26-OC12USG.ai (b) 1-hydroxyhexan-3-one Biology 12 Study Guide 0176520848 Biology 12 Study Guide 0176520848 Figure C01-F23-OC12USG.ai 14 Number Unit 1 • Organic Chemistry Figure Number Company MPS Company Technical Technical Pass 1st pass Pass SciSG_Che_Ch01.indd 14 C01-F25-OC12USG.ai NEL MPS 1st pass 2/24/12 6:34 PM 4. Draw a line diagram for 2-ethylpentanal. K/U C 5. Which of the following is a property of aldehydes and ketones? K/U (a) Their boiling points are higher than similar alcohols. (b) The molecules are polar and form hydrogen bonds with one another. (c) The molecules are more soluble in water than similar-sized alcohol molecules. (d) The solubility in water decreases as additional carbons are added to the chain. MAIN IDEA: The controlled oxidation of a primary alcohol produces an aldehyde. The controlled oxidation of a secondary alcohol produces a ketone. Tertiary alcohols do not readily undergo controlled oxidation. The hydrogenation of an aldehyde produces a primary alcohol. The hydrogenation of a ketone produces a secondary alcohol. 6. Complete the chemical equation for each of the following controlled oxidations of alcohol. Draw the structure of the product and write the IUPAC names of the reactant and product. T/I C (a) H CH3 CH CH2 CH3 C OH (O) H Reactant: Product: (b) OH CH3 CH C CH3 (O) CH3 H C01-F27-OC12USG.ai Reactant: Product: (c) OH H CH3 C CH CH3 (O) CH3 C01-F28-OC12USG.ai 12 Study Guide Reactant: Product: NEL 1.5 Aldehydes and Ketones 15 48 mber C01-F27-OC12USG.ai MPS SciSG_Che_Ch01.indd 15 2/24/12 6:34 PM 7. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: When a primary alcohol is hydrogenated, the carbonyl group forms on the terminal carbon atom, resulting in an aldehyde. K/U 8. Which of the following is a condensed formula for 4-methylhexan-2-one? K/U (a) CH3CH2CH(CH3)CH2COCH3 (b) CH3CH(CH3)CH2COCH2CH3 (c) CH3COCH2CH2CH(CH3)CH3 (d) HCOCH2CH2CH(CH3)CH2CH3 9. Complete Table 1 for the hydrogenation reactions of aldehydes and ketones. K/U C Table 1 Hydrogenation of Aldehydes and Ketones Reactant Product 18 or 28 alcohol (a) Name: Name: (b) O Name: Name: (c) OH C01-F30-OC12USG.ai O Name: Name: C01-F31-OC12USG.ai Biology 12 Study Guide 0176520848 Figure Number C01-F30-OC12USG.ai Company C01-F32-OC12USG.ai MPS Technical 16 Unit 1 • Organic Chemistry Pass 1st pass NEL Approved Biology 12 Study Guide Not Approved SciSG_Che_Ch01.indd 0176520848 16 2/24/12 6:34 PM 1.6 Carboxylic Acid, Esters, and Fats Vocabulary carboxylic acid esterification fatty acid carboxyl group hydrolysis triglyceride ester lipid saponification Textbook pp. 47–55 MAIN IDEA: A carboxyl group is a combination of a carbonyl group, C w O, and a hydroxyl group, –OH. Carboxylic acids are named by replacing the –e ending of the alkane with –oic acid. Carboxylic acids are formed by the controlled oxidation of aldehydes. 1. Write two common uses of each carboxylic acid. K/U (a) methanoic acid (b) ethanoic acid 2. Name each of the following carboxylic acids. K/U (a) O CH3 HO C CH2 CH2 CH2 CH CI (b) HOOCCH2CH2COOH (c) OH O Learning Tip IUPAC and Common Names You have probably realized that many compounds have both common names and systematic IUPAC names. The textbook mostly uses the systematic names as they help with visualizing the molecular structure of the compound. However, some common names are so familiar that they are also recognized by IUPAC. Acetic acid and formic acid are two such names. You should be familiar with the common names as well as the systematic names of these compounds. C01-F33-OC12USG.ai 3. Draw a structural formula for each of the following carboxylic acids. K/U C (a) 2,2-dimethylpropanoic acid (c) 2-ethyl-3-methylbutanoic acid (b) 3-methylbenzoic acid C01-F34-OC12USG.ai 2 Study Guide 48 mber C01-F33-OC12USG.ai MPS 1st pass NEL 1.6 Carboxylic Acid, Esters, and Fats 17 ved uide SciSG_Che_Ch01.indd 17 2/24/12 6:34 PM 4. Which of the following compound has the highest melting point? K/U (a) butane (b) propane (c) butanoic acid (d) propanoic acid 5. Use condensed formulas to write a chemical equation for the controlled oxidation of 2-methylpropanal to produce a carboxylic acid. Also write the IUPAC name of the product. K/U C MAIN IDEA: An ester’s name is derived from the name of the alkyl group of alcohol followed by the name of the alkyl group of the carboxylic acid with the ending –oate. Esterification is the formation of an ester from a carboxylic acid and an alcohol. Hydrolysis of esters is the breaking down of the ester by a strong base to form the carboxylic acid and alcohol. 6. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: The functional group of an ester is similar to a carboxyl group except that the carbonyl group is replaced with an alkyl group. K/U 7. Name each of the following esters. K/U O (a) CH3 CH2 CH2 C O CH2 CH3 (b) O O 8. The IUPAC name of this ester is ethyl 2-methylpropanoate. O CH3 CH C O CH2 CH3 CH3 K/U C C01-F35-OC12USG.ai (a) Write a condensed formula for the ester. (b) Draw a line diagram for the ester. C01-F36-OC12USG.ai C01-F37-OC12USG.ai Biology 12 Study Guide 18 0176520848 Unit 1 • Organic Chemistry Figure Number Company Technical SciSG_Che_Ch01.indd 18 NEL C01-F35-OC12USG.ai MPS 2/24/12 6:34 PM 9. Use structural formulas to write a chemical equation for the preparation of ethyl pentanoate from an acid and an alcohol. Name the reactants and products, and state the type of reaction. T/I C 10. What are the products from the hydrolysis of methyl propanoate? K/U MAIN IDEA: Fats and oils are triglycerides. They are esters made from long chains of fatty acids. Saponification is the process by which a fatty acid reacts with a strong base to form a salt of the fatty acid: soap. Saponification is a type of esterification. 11. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: Fats and oils are large ester molecules known as lipids. Fats and oils have the same general structure, with fats referring to solids and oils referring to liquids at room temperature. K/U 12. Soap is a sodium salt of a ______________________. It is formed together with glycerol when an ester called ______________________ is heated with the strong base sodium hydroxide in a type of reaction classified as ______________________. K/U 13. Which of the following is not true for trans fats? K/U (a) They have unsaturated hydrocarbon chains containing double bonds that cannot be rotated. (b) Their melting points are lower than the corresponding cis forms, since their molecules are more tightly packed together. (c) Eating foods containing them could lead to health problems as they are not easily digested as saturated fats. (d) They are not water soluble because of the non-polar nature of the long hydrocarbon chains in their molecules. NEL SciSG_Che_Ch01.indd 19 1.6 Carboxylic Acid, Esters, and Fats 19 2/24/12 6:34 PM 1.7 Amines and Amides Vocabulary Textbook pp. 56–62 amine amide MAIN IDEA: Amines can be viewed as alkyl groups bonded to a nitrogen atom or an amino group bonded to an alkane. Primary amines have one alkyl group attached to the nitrogen atom; secondary amines have two; tertiary amines have three. Amines are named by adding the suffix –amine to the root of the name of the longest alkyl group attached to the nitrogen atom. The prefix N- indicates that a second (or third) alkyl group is also attached to the nitrogen atom. 1. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: The IUPAC name for an aromatic amine consisting of an amine group attached to a benzene ring is benzamine. K/U Study Tip Structures of Amines To draw the structure of an amine, remember that an amine is a derivative of ammonia in which one or more of the hydrogen atoms are replaced with alkyl groups. 2. Name each of the following amines. (a) H CH3CH2CH N CH2Cl CH3 K/U (b) CH3 N CH3 3. Draw the structural formulas for all primary amines with the molecular formula C4H11N. Write the names of the isomers. K/U C C01-F38-OC12USG.ai C01-F39-OC12USG.ai Biology 12 Study Guide 0176520848 Biology 12 Study Guide 0176520848 20 Number Unit 1 • Organic Chemistry Figure C01-F38-OC12USG.ai Figure Number Company MPS Technical Company Pass Technical SciSG_Che_Ch01.indd 20 1st pass Pass NEL C01-F39-OC12USG.ai MPS 1st pass 2/24/12 6:34 PM 4. Name each of the following isomers of an amine with molecular formula C4H11N. Classify the amine as secondary or tertiary. K/U (a) CH CH CH 3 2 2 (b) CH3CH2 N N H CH3 H CH2CH3 (c) CH3 CH3CH2 N CH3 (d) C01-F40-OC12USG.ai H CH3CH N CH3 CH3 C01-F41-OC12USG.ai 5. Draw the structure of a tertiary amine with molecular formula C5H13N that has only one methyl group attached to the nitrogen atom. Write the name of this amine. T/I C C01-F42-OC12USG.ai Guide C01-F40-OC12USG.ai C01-F43-OC12USG.ai MPS 1st pass Guide 6. Is the following statement true or false? If you think the statement is false, rewrite it to make it true: The boiling points of amines of similar size increases C01-F41-OC12USG.ai from primary to secondary to tertiary as the number of hydrogen bonds that MPS the amine can form increases. K/U uide1st pass C01-F42-OC12USG.ai MPS uide 1st pass C01-F43-OC12USG.ai MPS 1st pass NEL SciSG_Che_Ch01.indd 21 1.7 Amines and Amides 21 2/24/12 6:34 PM 7. An amine can generally be synthesized from the reaction of _________________ and ammonia. The reaction gives a mixture of primary, secondary, and tertiary amines, which are separated using the process of _________________ since they all have different boiling points. K/U MAIN IDEA: Amides are formed from the reaction of carboxylic acid and amines. Amides can be hydrolyzed to reform the amine and carboxylic acid. Amides are named with the root of the name of the carboxylic acid first, followed by the root of the name of the amine, and ending with –amide. 8. Write the IUPAC name of each of the following amides. K/U (a) O CH3 CH3 CH2 (b) CH3 CH2 CH2 C O CH3 C N NH CH2 CH CH3 CH3 9. Which of the following is true for amides? K/U (a) The solubility in water increases with the length of the carbon chain. (b) Amides are structurally similar to esters, so they generally have a pleasant odour. C01-F45-OC12USG.ai (c) Primary amides have higher melting points and boiling points than similar amides. (d) Amides can be prepared by the hydrolysis reaction of a carboxylic acid with ammonia or an amine. 10. Name a carboxylic acid and an amine that can be used to prepare N,Ndimethyl-3-methylbutanamide. Write a chemical equation to show the C01-F44-OC12USG.ai T/I C reaction. Biology 12 Study Guide 0176520848 Figure Number C01-F45-OC12USG.ai Company MPS Technical Pass 1st pass Biology 12 Study Guide Approved 0176520848 Not Approved Figure Number Company C01-F44-OC12USG.ai MPS Technical Pass 1st pass Approved 22 Unit 1 • Organic Chemistry Not Approved SciSG_Che_Ch01.indd 22 NEL 2/24/12 6:34 PM CHAPTER 1 Summary Organic Compounds Organic chemistry is defined as the study of carbon-containing compounds and their properties. There are a few carbon compounds, including carbon oxides and carbonates, that we consider to be inorganic. Organic molecules may contain one carbon atom or tens of thousands of carbon atoms. The following graphic organizer summarizes some of the main ideas from Chapter 1. Add to it to create your own study notes. Organic compounds classes of compound structures • naming of compounds functional groups • properties C • polarity of molecules • based on: alkanes • structural formulas C • • • alkenes reactions • • alkynes alcohols • addition - substituent groups: • alkyl - • - • - • • • aldehydes • impacts on society and environment • • ketones • uses carboxylic acids amines hazards • • • • • • • • • amides NEL SciSG_Che_Ch01.indd 23 • Chapter 1 Summary 23 2/24/12 6:34 PM CHAPTER K/U T/I C A 1 Questions (a) Cl H3C CH CH2 CH CH3 O (b) CH3 CH2 C O CH O H3C (c) OH HO (f) CH3CH2COCH2OH (g) HCCCH2CHBrCH2CH(CH3)CH3 C01-F51-OC12USG.ai C01-F47-OC12USG.ai (h) H2NCH2CH2CHNH2CH3 N (d) C CH3 Br K/U (e) CH3 CH3 O C01-F48-OC12USG.ai 2. Draw a structure for each of the following compounds. (1.4, 1.6) (a) line diagram for 3,5-diethyloctan-4-ol Biology 12 Study Guide 0176520848 0176520848 Figure Number C01-F47-OC12USG.ai Company MPS Figure Number Company K/U C C01-F49-OC12USG.ai Biology 12 Study Guide C01-F51-OC12USG.ai MPS Technical (b) condensed formula for 3-chloro-2-methylbutanoic acid C01-F50-OC12USG.ai Pass 1st pass 1st pass Technical Pass Approved Approved Biology 12 Study Guide Not Approved Not Approved 0176520848 Figure Number C01-F48-OC12USG.ai Company MPS Technical Pass Biology 12 Study Guide 1st pass Approved 0176520848 Not Approved Figure Number C01-F49-OC12USG.ai Company MPS Technical 24 Unit 1 • Organic Chemistry 2 Study Guide Pass 1st pass 48 Approved mber 1. Name each of the following compounds. (1.1, 1.2, 1.3, 1.5, 1.6, 1.7) Knowledge/Understanding Thinking/Investigation Communication Application NEL C01-F50-OC12USG.ai Not Approved SciSG_Che_Ch01.indd 24 MPS 2/24/12 6:34 PM 3. Which of the following compounds does not form hydrogen bonds with water? (1.4, 1.5, 1.6, 1.7) K/U (a) ketone (b) primary amine (c) carboxylic acid (d) primary alcohol 4. Which of the following compounds is an ether? (1.4, 1.6, 1.7) K/U (a) aniline (b) ethanamide (c) methoxyethane (d) methyl ethanoate 5. Indicate whether each of the following statements is true or false. If you think a statement is false, rewrite it to make it true. (1.1, 1.2, 1.3, 1.7) K/U (a) Bonds between carbon and hydrogen in saturated hydrocarbons are almost non-polar, so these compounds have lower melting points and boiling points than compounds of similar sizes. (b) The melting points of trans isomers are lower than the corresponding cis forms because their molecules are more tightly packed together. (c) An aromatic hydrocarbon is an unsaturated hydrocarbon that has a ring structure and a bonding arrangement that causes it to be chemically stable. (d) Since nitrogen is more electronegative than either carbon or oxygen, the N–C bonds and any N–H bonds in amines are polar. 6. Complete Table 1 for simple organic compounds and their reactions. (1.1–1.7) K/U T/I Table 1 Organic Compounds and Their Reactions Reaction Reactants Products methane 1 oxygen carbon dioxide 1 water ethene 1 hydrogen substitution dehydration chlorobenzene propanol methanol 1 ethanol methoxyethane 1 water ethanol 1 oxygen ethanal 1 water esterification methyl propanoate 1 water methyl ethanoate 1 water condensation NEL SciSG_Che_Ch01.indd 25 ethanoic acid 1 methanol ethanoic acid 1 ammonia Chapter 1 Questions 25 2/24/12 6:34 PM