Organic Nomenclature Problem Set SCH4U Organic Chemistry Aliphatic Hydrocarbons Practice Alkanes 1. Butane exists in the form of two structural isomers. Draw the structural formula and write the IUPAC name of each. 2. Draw the condensed straight-chain structures for heptane and nonane. 3. Match each name in a-d with the correct structure in e-h. a. b. c. d. 3-ethyl-2-methylhexane 3-ethyl-4-methylhexane 2,2- dimethylhexane 3-ethylhexane H e. H H H H H H f. C C C C C H H H H C H H H H H C C C H H H H H H H C C C C H H H H H H C H H C H H C H H C H H H g. h. H H C H H H C C H H C H H H H H H C C C C H H H H H H H H H H C C C H H H H C H H C H C H H H C C C H H H H H 4. How many hydrogen atoms would be in a molecule of an alkane containing 15 carbon atoms? 50 carbon atoms? 1 SCH4U&–&Hydrocarbons&Worksheet& mes(for(the(following:( 5. Using IUPAC rules, write the names of the following alkanes: a. H H H C H H H C C H H e. H H H C H C H C H H H H H C C C H H H C C C H H H H H H b. H H H H C C C H H C H H C H H H f. H c. H SCH4U&–&Hydrocarbons&Worksheet& H H C H H C H H H C H H H C C C C C C H H H C H H H C H d. ctural(and(line(diagrams(for(the(following:( H H H es(for(the(following:( hept-3-ene C H H H H C H H H H g. CH3-CH2-CH-CH(CH3)-CH2-CH3 6<cyclopropyl<2<methyl<4<propyl<hept<2<ene( 6. Draw LINE and EXPANDED MOLECULAR structures for the following: (a) 3-methyl hexane openta<1,3<diene( ( ( 1,3,3<trimethylcyclobutane( (b) 2,2-dimethyl propane (c) 2,3-dimethyl pentane (d) 4-ethyl-2-methyl octane (e) 4-ethyl-3,3-dimethyl octane (f) 2,2,3-trimethyl pentane ( ( ( 4<methyl<3<phenyl<hex<1<yne( (g)( 4-ethyl-2,4-dimethyl heptane ural(and(line(diagrams(for(the(following:( 2 7. Explain why the following names are incorrect. Draw the structural formula and name each one correctly. (a) 1,3-dimethyl butane (b) 4 -methyl petane (c) 4,4-dimethyl hexane 8. Use data books to draw a graph of the molecular mass of the first 10 straight chain alkanes against their boiling points. What can you deduce from this graph? Alkenes & Alkynes 9. Draw structures for the following: (a) hex-2-ene (b) 3-methyl pent-1-yne (c) 2,3-dimethyl but-2-ene (d) 2-methyl hex-2-ene (e) but-1-ene (f) pent-2-yne (g) 2,5,5,6-tetramethyl hept-3-yne (h) 1,2-dibromo but-1-ene (i) 3,4-dibromo-5-ethyl-2,6,6 -trimethyl octane 10. Using IUPAC rules, name the following structures. H C H H H H H H C H C H C H H C H C H H C C C H H C H C H Write the names for the following hydrocarbons: H C H H H H Write the names for the following hydrocarbons: H C C H H C C H H C H C H H H C C H H H H Draw structures for the following: 3 heptyne cyclopentene 1,3 butadiene 3 (C2H4) (C2H2) ene prop ………… ene prop yne ......) (C(....…......) (C3H4) 3H6) 4), 7-heptane(C 8-octane (C8H18), 9-nonane(C9H20), 10- decane (C10H22), X-(CxH2x+2). but ene 7H16),………… (.…........) Alkanes, Alkenes, Alkynes and Cyclic Hydrocarbons (....…......) xane(C6H14),Using 7-heptane(C (C8Hthe 9-nonane(C 7H16), 8-octane 18), following 9H20), 10- decane (C10H22), X-(CxH2x+2). IUPAC Rules, name or draw compounds: 1-9 *pg 4-5-Nelson Chem 12 *pg 15-16- Nelson Chem 12 ture practice 1&2 Chemical structure IUPAC Name practice 3, 4, 5& 6 *pg 18-19- Nelson Chem 12 *pg 4-5Nelson practice 1-9 7&8 *pg 21- Nelson Chem 12 Chem 12 1 practice 1&2 *pg 15-16- Nelson Chem 12 4, 5& 6system of nomenclature *pg 18-19- Nelson Chem 12 ckynes: compounds practice using the3,IUPAC cs)–CH2–CH3 practice &8 *pg 21- Nelson Chem 12 b) CH72–CºC–C(NO 2)–CBr–CH3 | | | 2 g organic compounds using the IUPAC system C3H7 CH3 CH3 of nomenclature H=C(CH b) CH2–CºC–C(NO2)–CBr–CH3 3)–CH2–CH3 ....................... ..........................................………........................................... Br Cl | Br | CH | 3 H C CH CH CH CH C C3H7 CH Cl CH3 CH3 3 2 3 3 .......................................... H3 ..........................................………........................................... CH3 d) CHI 4 2–CBr2–CCl2–CH3 H3C C ..... e) CF2=CF2 CH2 CH2 CH NO2 CH2 CH2 CH2 NH2 ........................................................................ ................................................................... CH3 H2)–CI–CH3 5 d) CHI2–CBr2–CCl2–CH3 CH=C-CH(CH3)-CH3 h) ........................ ........................................................................ ..... Cl CH3 CH2 Cl HC CH CH CH 6 g) CH=C-CH(CH 3)-CH 3 CH Cl CH3 2 2 Cl Cl CH h) e) CF2=CF2 C3H7 ................................................................... CH-CH3 C3H7 Br CH3 Cl CH 3 ........................................................................ ................................................................... CH-CH3 7 NH2 NH2 C CH Br CH3 NO 3–CH NO – CH–CH3 –CH(NO2)–C2H5 j) CH k) CH2=CH–CH=CH2 ........................ ........................................................................ ................................................................... | | Cl Cl Cl 8 .................................... Cl C CH CH 3–CH C CH 2 CCH CH 2–C2H5 H3C C CH2 3 2 2 2 Cl 2 3 Cl Cl .................................... ............................................................. ………………………………… H(NO k) CH2=CH–CH=CH2 2)–CH(NO2)–C2H5 j) CH3–CH – CH–CH3 CH | | CH Br 9 ....................................................... CHCH3–CH2 CH2–C2H5 H C C CH CH 3 2 3 2 CH3 ............... ....................................... 10 3 ............................................................. ………………………………… Br H3C CH2 C CH2 CH3 Cl 11 NO2 H3C CH Br CH2 CH2 4 2,3-dichloropentane 12 3-bromo-2-methylheptane 13 1,2-dichloropropene 14 4,4-diamino-2,3,6-trichlorooctane 15 2,2,3,3,4-pentachloropentane 16 17 H3C CH2 CH CH2 CH3 CH2 18 H3C CH2 19 CH C CH2 CH2 CH3 Cl H3C CH CH CH CH CH3 CH CH3 NO2 Cl 20 H3C CH2 CH CH Cl 21 CH3 H3C C CH2 Cl Br Br C C CH3 CH3 22 5 23 H3C CH3 CH3 C C CH3 CH3 CH2 Cl Cl C C CH3 5-amino-3-chloro-pent-1-ene 24 4-chloro-2,2-dinitro-hept-3-ene 26 trans-3-octene 27 28 CH2 Cl H3C C C C CH3 Cl 29 HC 30 C H3C Br Br CH CH C C CH2 CH3 CH3 5,5-dimethyl-hex-2-yne 31 5-amino-hept-3-yne 32 a. pentane b. 2-pentene 33 34 c. 1-pentyne H2 C H3C CH CH CH3 CH2 35 CH3 C2H5 36 C2H5 6 ce 1&2 ce 3, 4, 5& 6 ce 7 & 8 H *pg 4-5-Nelson Chem 12 *pg 15-16- Nelson Chem 12 H 18-19- NelsonHChem 12 *pg *pg C 21-CNelson C Chem C 12 H 37 H H H C H ds using the IUPAC system ofH nomenclature H3 b) CH2–CºC–C(NO2)–CBr–CH 3 H H| | | H C3H7 CH3H CCH3C C 38 ..........................................………........................................... H 40 H CHI2–CBr2–CCl2–CH3 H H H H C C H e) H CF H C C 2=CF2 C H H ........................................................... ................................................................... 41 H(CH3)-CH3 Cl H C C H h) C3H7 42 CH-CH3 Br CH3 H ........................................................... ................................................................... H C H –C2H5 j) CH3–CH – CH–CH3 k) CH2=CH–CH=CH2 |43 | ............ CH3–CH2 CH2–C2H5 H ........... ............................................................. H C ………………………………… H 44 (C6H10) 45 (C12H26) (recall that in line diagrams, lines represent carboncarbon bonds; this contains isopropyl) 46 (C12H24) 47 (C9H16) 48 1,3-diaminopropane (line diagram) 49 50 trans-5-ethyl-4,5-dimethyl-hept-2-ene (line diagram) H3C H C H C CH2 CH2 CH3 (indicate if it is cis or trans isomer) 7 Aromatic Hydrocarbons Chemical structure IUPAC Name 1a Cl Cl Cl 1b O2 N O2 N O2 N 2a H3 C O2 N 2b Cl Cl OH Cl Cl 3 p-nitrophenol 4 2,3-dibromo-5-chloro nitrobenzene 5 Consider the following structure representing a benzene molecule substituted with a number of different groups. (A, B, C, D, E and F A F B E C State whether the following pairs of groups are ortho, meta or para to each other. a) b) c) d) e) B&D F&C E&F A&C B&E f) F & B g) B & C h) F & A i) E & C D 8 Isomers 1. Which of these pairs are structural isomers? H H Cl a. Cl C C H H Cl H Br Br C C H H b. H C C H H Cl Br H C C H Br c. H H Cl C C H H Cl H Cl Cl C C H H H H d. H H H C H H H H C C C H H H C H C H H H H C H H C H H e. H H H O H C C C H H H H H H H H C C C H H H OH 2. Examine each of the following pairs of structures and decide if the two are identical, isomers or different compounds. a. Chemical structure Chemical structure CH3 H3 C CH3 CH2 H3 C d. CH3 CH3 b. c. Identical / isomers/ different compounds CH3 H3C CH2 OH CH2 H3C H3 C H2C H3C CH CH2 CH2 OH CH2 CH2 CH2 e. 9 O H3C O C H H C CH3 CH3 CH3 f. H3C H3C CH CH CH3 CH3 g. H H3C CH2 NH2 H3C N CH3 O O h. H3 C CH2 C O H H O C O i. H CH2 CH3 O H O C O CH2 CH3 H3 C CH2 C O O j. H k. C O CH2 CH2 OH HO CH2 O C OH O H3C C CH2CH3 H3C CH2 CH H3C CH2 CH3 H2C CH2 l. H2C C CH3 CH3 CH3 C CH3 H3C CH CH2 CH2 HC CH3 CH2 CH3 CH3 C CH CH3 CH3 CH3 O O m. H3C NH C CH3 H3C CH2 C NH2 n. H O O H o. H O H H3C CH3 C H3C p. H3C H3C C H H3C C H3C CH2 C H C CH3 H3C CH3 CH2 C C H H3C H C CH3 10 Alcohols, Aldehydes, Ketones and Carboxylic Acids Using IUPAC rules, name or draw the following compounds: Chemical structure 1 2 CH3CH(NO2)CH2CH2OH H3C Cl Cl C CH Cl 3 IUPAC Name Cl H3C CH CH3 OH H2 C CH2 CH2 C CH2 CH3 CH OH Cl 2,5-dinitro-hexan-3-ol 4 2,2-diamino propanol 5 H 6 H3C 7 8 CH CH Cl Cl CH3 CH2 C CH3 H H3C CH CH2 CH C H3C CH2 CH2 C CH2 O O CH3 O NO2 9 H3C C O CH2 C CH3 NO2 10 2-chloro-2-methyl propanal 11a H3 C CH2 11b H3 C COOH 11c CH2 COOH H COOH 11 COOH 12 H3C CH2 CH CH CH2 CH3 CH3 13 NO2 H3C CH CH CH CH2 COOH cis-4,5-dichloro-hept-4-enoic acid 14 For each of the following, state the functional group name the organic compound O 15a H3C C O 15b 15c H H3C C H2C CH2 OH CH3 OH 15d H3C C CH2 CH3 O 15e H C CH2 CH3 O 15f CH3 H3 C C O 12 Ethers, Esters, Amines and Amides Using IUPAC rules, name or draw the following compounds: Chemical structure IUPAC Name 1 O 2 O O NH2 F 3 4 N-butyl hexanamide O 5 N H 6 O 7 NH2 8 N O 9 10 3-methoxy-5-methyl-4-nitro-heptane N-isopropyl ethanamide 11 13 O O CH2 CH3 12 CH3CH2CH2 N CH2 CH2 CH2 CH3 13 2,3-dibromo-5-aminononane 14 2-chloropropyl butanoate Cl 15 O N-ethyl-N-methyl trans-4,5-difluoro-4-octenamide 16 For each of the following, state the type of functional group(s) and name the organic compound O 17 CH3 O H 18 H N 19 O O 20 21 N N 22 O O 14 Organic Compounds and Functional groups 1. Name the type of organic compound each of the following would be classified as: a. Propanol b. Aminoethane c. Butanone d. Methoxymethane e. Ethanal O H H H H f. O C C H h H C C H C C . H H H H . H . g. H H H C C H H O H i C H C O H OH H H C C H H H 2. Write the name for each of the following: a. H H C C H H H b. H H O H H C C C C H H H c. f. O g. H H H e. H OH H C C C H H H H H C H O C H H N H O C C h. H C H C H H C d. H H H H O H H i. H H C C C C H H H H j. H H C H H H H C C C C H H H H H H C H N H H H H H H H H H C C C H H H H H H C C C H H H H OH H O C OH 15 3. Name the type of organic compound each of the following would be classified as: a. b. g. H3C CH2 C O CH2 CH3 H3C CH2 d. H3C CH2 C O j. CH3 O CH2 CH3 l. C OH O k. CH2 CH3 i. C16H34 H3C H C H f. C O H e. CH2 H3C OH C H3C h. O c. O H2C C OH CH CH2 CH3 4. Draw the structural formula for: a. b. c. d. methoxymethane 1-pentanol 1-aminobutane propanal e. f. g. h. 2-propanol 2-methyl-octan-4-ol 2-methoxypropane propyl ethanoate 5. Name the type of organic compound each of the following would be classified as: a. k. O H3C C H3C CH2 CH2 CH3 C H3C b. c. CH2 CH C d. H3C C CH3 CH3 CH3 m. O HO C l. CH3 H3C CH3 CH2 CH3 CH3 CH CH CH3 n. CH3 16 e. o. H3C CH3 O H3C CH C CH CH3 f. H3C g. O CH2 p. CH3 C CH2 H3C CH2 H3C O i. CH2 CH2 C H O C CH2 COOH CH2 CH CH3 O H3C CH2 O C s. H3C CH2 OH t. H3C CH2 CH2 CH3 CH3 CH3 C CH2 r. O HO CH2 OH H3C CH2 CH3 h. j. CH2 CH3 q. O H H3C CH3 CH2 O H CH3 CH3 Name or draw the following compounds: Chemical structure IUPAC name 6. ethoxyethane Cl 7. 8. H3C CH H2 N CH2 CH2 CH2 CH2 CH CH3 O CH2 CH2 CH3 CH3 O 9. H3C CH2 CH2 C O CH2 CH2 CH3 17 Types of Organic Reactions 1. Identify the type of organic reaction represented by each of the following equations: a. H H H C C H H + H H H C C H H heat Br Br H + Br HBr b. H H H C C H H + C H2O H H H H H C C C H OH H c. H Cl H3C C + 2HCl CH H3C C CH3 Cl d. H H C H C C H Br H C C H H H C + H Br Br H C H C H C H H C H C H H H H e. C Br H OH CH2 CH2 HC conc. H2SO4 H2C f. H H H h. H C H H g. H K2Cr2O7 C H H H C C C H H H H H + CH CH2 CH2 O C H2C CH2 CH2 CH 2 Cl O C OH Cl CH2 H H Cl Cl C C C H H H H + 2 HCl NO 2 CH CH HC CH CH CH CH + HNO3 C HC CH CH CH 2. Write the equation for the addition reaction involving propene and bromine. 18 3. Complete the following equations by writing the structures of the products that form. If no reaction occurs, write “no reaction”. a. H3C CH H3C CH + HO CH2 2 acid catalyst b. c. CH CH3 + H2O acid catalyst Br + Br2 (3 possible products but ortho isomer is favoured) d. H3C CH2 CH2 CH3 + HO 2 e. OH conc. H2SO4 + H2O f. O C H3C + CH3 K2Cr2O7 g. CH2 H3C O CH + K2Cr2O7 h. CH H3C CH3 CH + , pressure H2 Pt catalyst 4. a) Write the equation for the complete oxidation (combustion) of 2-butanol. b) Write the equation for the mild oxidation of 2-butanol with KMnO4. 19 5. Write the equation for the addition of hydrochloric acid to ethene. What is the name of the product formed? 6. Predict the product formed when HCl is reacted with each of the following compounds. Use Markovnikov’s Rule to predict the product. a. H3C CH H3C CH3 C b. H3C c. H3C CH2 C H C CH 7. Describe the chemical test that could be carried out to distinguish between hexane and hexene. 8. Write the equation for the substitution reaction involving one molecule of each of ethane and bromine. 9. What is the structure of the missing organic reactant in each of the following: + , pressure H2 Pt Catalyst 10. Write the structure of the carboxylic acid that forms when the following aldehyde is oxidized: CH2 H3C O CH 11. Which of these two compounds is easily oxidized by KMnO4? Write the structure of the organic product of the oxidation. O a. H3C CH3 O b. H3C CH2 C H 12. What are the products of the mild oxidation of a. 1-propanol b. 2-propanol 20 Types of Organic Reactions II 1. Identify the type(s) of organic reaction represented by each of the following equations and name the compound produced. a. H H H O H C C + C OH H O H b. H2C CH2 H H C C H H H + H C C H H O C OH H2SO4 H2O H H H3C CH2 + O H H C C H H H + H2SO4 H3C H3C OH CH2 O c. H2O CH3 O O C C OH NH CH2 CH2 CH3 + H3C CH2 CH2 NH2 2. Write the formula for the primary amine produced from the reaction of iodocyclopentane and ammonia. 3. Complete the following equations by writing the structures of the products that form OR the reactants required. If no reaction occurs, write “no reaction”. a. ammonia + bromocyclohexane b. H2SO4 ethanol + 2-propanol c. H3C O CH2 CH3 + HO 2 d. H 2SO 4 heat O CH2 O C CH2 CH3 + H2O e. O C H3C OH + 2SO4 HO CH3 21 4. a) Write the equation for the condensation of 1-butanol. Name the product. b) Write the equation for the condensation of 1-aminopentane and butanoic acid. Name the product. 5. What is the structure of the missing organic reactant in each of the following: O + HO 2 H3C excess + HO OH CH3 a. 6. Which of these four compounds will undergo an acid-catalyzed reaction with methanoic acid? Write the structure of the organic product in each case. O a. H3C CH3 O H3C C b. NH2 OH c. H3C d. H3C CH CH3 O CH2 C H 7. a) Write the equation for the reaction of 2-butanol with 2-pentenoic acid. b) What is the name of the product? 8. Write the structural formulas of the alcohol and the carboxylic acid from which the following ester can be made. H H H H C C C H H H O C O H H C C H H H 22 9. Write formulas for all organic molecules and show the reagents required to produce each of the following from an alkene: a. Butanoic acid d. 3-pentamine b. 2-pentanone e. propyl butanoate c. 2-pentanol f. butyl proanamide 10. Which of the following will be split apart by hydrolysis (reaction with water), and what are the structures of the products that form? a. CH2 H3C O CH2 CH3 O CH2 C b. H3C O CH3 Polymerization 1. Identify the type of polymerization in each of the following: a. H N H H N H b. H H H C C H O + N O H H C C N H H H H C C C H H H HO C C H H H H H C O H C C H OH H N C C N H H H H H C H O H H + H C H H C O C C H C C OH + 3H 2 O H H3O+ H H O H H H H C C C C C H H H H H H C H 23 2. For each of the following, draw three linked monomer units of the polymer’s structure: Monomer a. F F C C F F Polymer Teflon (non-stick coating) Tedlar (used to weatherproof building materials) F c. H2 C C CH3 d. H Cl C C H H Structure Polyvinyl chloride (PVC) Polystyrene (#6 plastic) e. CH CH2 3. Draw the structure for the monomer(s) from which the following polymer is made and name the type of polymer (addition, polyester or polyamide). a) PETE (polyethylene terephthalate) O CH2 CH2 O O O C C O CH2 CH2 H CH3 H CH3 H CH3 H CH3 C C C C C C C C H H H H H H H H O O O C C O CH2 CH2 O O O C C b) PP (polypropylen e) 4. Draw the structure of the polymer which would form when the following molecules react. (draw two units) O H N H C H + CH2 N H HO CH2 CH2 O C OH 24