1.8. Organic Chemistry. Practice Exam Organic Chem. System LENGTH: VOLUME MASS Temperature. 1 gal = 4 qt. 1 lb = 16 oz.

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1 rganic hemistry Practice Exam rganic hem Name (last) (First) Read all questions before you start. Show all work and explain your answers to receive full credit. Report all numerical answers to the proper number of significant figures. By signing your signature above you agree that you have worked alone and neither give nor received help from any source. Keep your eyes on your own paper at all times System LENGT: VLUME MASS Temperature English: 1 ft = 12 in 1 gal = 4 qt 1 lb = 16 oz T! F = 1.8T! mile = 5280 ft 1 qt = in 3 1 ton = 2000 lb 1 yd = 3 ft SI- English: 1 in = 2.54 cm 1 mi = km 1 L = qt 1 qt = L 1 lb = g 1 oz = g T! = (T! F 32) 1.8 Misc. info 1 mole = R = J/ mol K or L atm/mol K Group Structural Feature Suffix. Alkane single bond -ane Alkene double bond -ene Alkyne triple bond -yne Alcohol - group -ol Ether R--R ether Aldehyde R -al Ketone R--R -one carboxylic acid R- -oic acid ester RR' -ate amine R R'R"N -amine amide R-NR' -amide Alkyl groups: Methyl Ethyl Propyl Butyl. n-prolyl n-butyl iso-propyl iso-butyl sec butyl n 2n+2 n 2n n 2n-2 # prefix Alkane Alkene Alkyne 1 meth- methane 2 eth- ethane ethene ethyne 3 prop- propane propene propyne 4 but- butane butene butyne 5 pent- pentane pentene pentyne 6 hex- hexane hexene hexyne 7 hept- heptane heptene heptyne 8 oct- octane octene octyne 9 non- nonane nonene nonyne 10 dec- decane decene decyne Reactivity Alkene & Alkynes 1 alogenation (+ X 2 ) 2 ydrogenation (+ 2 ) 3 ydrohalogenation (+ X ) 4 Polymerization tert butyl

2 Multiple -choice. Show work for partial credit. 1 The functional group of acetic acid is a) Alcohol b) aldehyde c) carboxylic acid d) ester e) ester 2 The VSEPR structure of methane is a) linear b) trigonal c) bent d) tetrahedral e) pyramid 3 A tertiary carbon is bonded directly to: a) 2-hydrogens b) 3 carbons c) tert-carbons d) 3-carbons e) 4-carbons 4 What is the name of the organic compound with the formula a) pentene b) heptene c) heptyne d) pentyne e) pentanol 5 The bond angle between for -- in methane is a) 180 b) 120 c) d) 90 e)not constant 6 Which is not an organic compounds a) sodium hydroxide b) octane c) ethanol d) toluene e) glycol 7 Which of the following formulas is/are correct organic structures? a) b) Br N c) d) Br N 8 Which of the following is a correct IUPA name. a) 4-methylpentane b) 4,4-dimethylhexane c) 3, 4-dimethylnonane d) 2-ethyl-3-methylhexane

3 9 The molecular formula for 5-butyl-2,4-dimethyldecane is a) 1532 b) 1736 c) 1430 d) 1634 e) Which of the following names is correct? a) 2-dimethylbutane b) 3-methylhexane c) 2-ethylpentane d) 2-methylcyclohexane 11 The name of the following structure is: Br Br F a) 1-chloro-2,2-dibromo-1-fluoro-1-methylethane b) 3,3-diboromo-2-chloro-2-fluoropropane c) 1,1-dibromo-2-chloro-2-fluoropropane d)1,1-dibromo-2,2 dichlorofluoropropane 12 Ethyne is a(n) a) alkane b) alkene c) alcohol d) aromatic e) alkyne 13 ow many alkyne isomers are possible with the molecular formula 610? a) 3 or less b) 4 c) 5 d) 6 e) 7 or more 14 Alkanes have the general formula a) n2n+2 b) n2n c) n2n-2 d) nn e) 5 15 Which of the following is an aromatic compound? (note: ydrogens are omitted for clarity) a) b) c) d) 16 Pentane has the formula a) 512 b) 510 c) 714 d) 716 e) 58

4 17 Which compound below is not an alcohol a) ethylene glycol b) calcium hydroxide c) phenol d) propanol e) vodka 3 ( 2 ) Name the following molecule: a) nonane b) decane c) octane d) octene e) nonene 19 What is the name for the following a) 2-methyl-3-propylheptane b) 2,2-dimethylpropane c) 2-methyl-3-butylhexane d) 4-isobutyloctane e) 4-isopropyloctane 20 The addition reaction between 2-pentene and hydrogen produces a) 2-pentane b) pentane c) 2-pentyne d) cyclopentane e) 2,3-dihydropentane 21 The classification of the following molecule is: a) alcohol b) aldehyde c) carboxylic acid d) ether e) butane 22 Which of the following functional groups does not contain a doubly-bonded oxygen a) aldehyde b) carboxylic acid c) ester d) ketone e) ether 23 What is the functional group for the compound a) hydroxide b) carboxylic acid c) amine d) ketone e) ester 24 ow many implied hydrogens are there in the hydrocarbon molecule shown? This structure is drawn with out hydrogens attached: a) 15 b) 9 c) 12 d) 16 e) 17

5 25 Which functional group(s) or class of organic compound(s) is not present in compound shown: a) amine b) ester c) alkene d) hydroxyl e) amide 3 N (16 pts) Draw the structure of each compound listed below. Some of the compounds named below are correct and others are incorrect. ircle the names that are incorrect and explain why the names are incorrect. Write the correct IUPA names for those compounds that you circled. i) 2-methyl-4-hexene ii) 2-ethylhexane iii) 1,4-dimethylcyclobutane iv) 3-ethyl-3,4-dimethylheptane orrect Name 5-methyl-2-hexene orrect Name 3-methylheptane orrect name 1,2-dimethylcyclobutane orrect name as given above 27 (16 pts) Determine the total isomers that can be formed from 4 carbon atoms, 7 hydrogen atoms and one chlorine atom (1 pt for each isomer). Draw stick forms for all isomers you have proposed. Label all chiral carbons in the isomers you have drawn with an asterisk (). Use the molecular modeling kit to assist you. For this question, points will be deducted for proposing identical structures or stating a carbon is chiral if it is not. t-1-chloro-1-butene c-1-chloro-1-butene 2-chloro-1-butene 3-chloro-1-butene 4-chloro-1-butene 1-chloro trans -2-butene 2-chloro trans-2-butene 1-chloro cis-2-butene 2-chloro cis-2-butene 1-chloro-2-methyl-1-propene 3-chloro-2-methyl-1-propene 3 1-chloro-1-methyl cyclopropane cis 1-chloro-2-methyl cyclopropane 3 trans 1-chloro-2-methyl cyclopropane 1-chloro cyclobutane 28