Organic Problems 1. Draw and name the isomers of C7H16 . 2. Name the following. CH3 a. CH3CHCH2CCH3 CH3 CH2 CH3 CH3 e. CH3CH2CCH2CCH3 HC CH3 CH3 c. CCH2CCH3 CH3 CH3 CH3 b. CH3 CH3 d. CH3 CH3 f. CH3 CH3CCH2CH2CHCHCH3 CH2CH3 CCCH2CH3 CH3 CH3 CH3 CH2 CH2 CH3CHCH2CH2CCH3 CH3 3. Name the following a. c. b. d. 4. Draw structural formulas for the following. a. 2,3,5,6-tetramethyloctane b. cis-3,4-dimethyl-3-hexene c. 1-ethyl-3-methylcycloheptane d. 4,4-dimethyl-2-pentyne e. 6-methyl-2,4-nonadiene f. ethylcyclopentane g. 2,3-dimethyl-1,3-butadiene 5. Draw and name 12 isomers that have the formula C6H12. e. 6. Complete and balance the following. a. CH3CH=CH2 + HCl → b. CH3CH=CHCH3 + Br2 → c. CH3C≡CH + 2 HBr → d. CH3C≡CCH3 + 2 F2 → e. 1,3-cyclohexadiene + excess chlorine gas → AlCl3 f. 1,4-dimethylbenzene + chlorine gas → 7. Name the following. a. CH2CH2 OH f. CH3 CH3CHCH2CH Br Br CH3 b. O g. CH3CHCH2CH3 CH3CCH2CHCH3 NH2 CH3 c. CH3 h. CH3 HC CH3CHCH2CHCHCH3 CCH2CHCH2CH3 CH2CH3 CH3 CH3 d. CH3CH i. CHCH2CCH3 CH3 e. O j. CH3CH2CHCH CH3 O CH3CH2CHCH2COH CH3 8. Draw structural formulas for the following: a. 3-hexanone b. trans-3-hexene c. iodobenzene d. propylbutanoate e. 2,3,4-trimethylhexane f. 3-methyloctanal g. 2-pentyne h. 1,2,3-triethylcyclohexane i. butylpropanoate j. the fat formed by hexanoic acid k. the oxidation product of 2-pentanol 2 9. Write formulas ``for the products and name all organic compounds in the following reactions: a. CH3C CH2 + HI CH3 O b. CH3CH2CHC H+ OH + CH3OH CH3 c. [O] CH3CH2CHCH2CH3 OH d. + Cl2 e. CH3CH2CH2CH2OH f. CH3CH2C CH [O] + [O] HCl O g. CH3CH2C O CH3 + NaOH 10. For the following compound, write a complete, expanded structural formula (with all C-H bonds, etc. clearly shown). Also, name the compound. O CN Name: 11. In the structure above, the hybridization at the carbon atom of the CN group is and the bond angles around that carbon are about 3 degrees. 12. Write chemical formulas for each of the following compounds. You may use partially condensed formulas (e.g. CH3-CH2-OH for ethanol) as long as the correct number of hydrogens are shown on each carbon and the C-C framework and any functional groups are clearly shown. a. b. c. d. aniline acetone "MTBE" (methyl tert-butyl ether) 4-amino-3-methylpentanal 13. Consider all possible carbonyl compounds having the formula C4H6O. a. Write expanded structural formulas for as many carbonyl isomers of C4H6O as you can (there are more than five). (Note: Points will be deducted if the same structure is drawn more than once but bonus points are available for each correct one beyond five!) b. One of the above carbonyl isomers (call it compound A) can be cleanly converted in a twostep sequence of reactions to 1,3-butadiene (compound C). Which carbonyl isomer is compound A? Write complete structural formulas for compounds A, B, and C in the reaction sequence below. A H2 H+ B C ∆ 14. Write complete, systematic names for: CH3 CH3 CH CH CH CH3 CH2 CH2 C N O H C CH2 CH2 CH CH2 CH3 CH3 C O CH O H2C CH3 CH3 OH H3C CH2 CH CH CH2 CH CH3 H2C CH2 CH3 4 15. Write complete, specific structural formulas for all of the organic reactants and products in each reaction. an ester 2-hexyne NaOH H2 sodium acetate cis-2-hexene H2O + 3-pentanol an alcohol 16. For the following compound, write a complete expanded structural formula (with all C-H bonds, etc. clearly shown). Also, name the compound. O 5 Organic Problems (Answers) Note that all structures are drawn with only skeletal carbons for simplicity in the drawing program. With pencil and paper you will BE REQUIRED to show the correct number of hydrogen atoms attached to each carbon. Please see me if you have questions about this. 1. Draw and name the isomers of C7H16 . Heptane C C C C C C C 2-methylhexane C 3-methylhexane C 2,2-dimethylpentane C C C C C C 2,3-dimethylpentane C C C C C C C C C C C 3,3-dimethylpentane C C 3-ethylpentane C C C C C C C C C C C C C C C C C 2,4-dimethylpentane C C C C C C CH3 CH2 C CH3 e. HC CH3 CH3 CCCH2CH3 CH3 2,2,4,4-tetramethylhexane 3,3-dimethyl-1-pentyne CH3 f. CH3CCH2CHCHCHCH3 CH2CH3 C C 2,4,4-trimethyl-1-pentene CH3 CH3 CH3 C CH3 CH3CH2CCH2CCH3 c. C CCH2CCH3 CH3 2,2,4-trimethylpentane b. C CH3 CH3 d. CH3CHCH2CCH3 C CH3 CH3 CH3 CH2 CH2 CH3CHCH2CHCHCH3 2,3,6,6-tetramethyloctane CH3 3,3,6-trimethyloctane 6 C 2,2,3-trimethylbutane C C 2. Name the following. CH3 a. C C 3. Name the following a. 4-methyl-2-pentene b. 2,3,4-trimethylhexane c. 3,6,dimethyl-1,4-cyclohexadiene d. 2,4-heptadiene e. 1,2-dimethylcyclopentane 4. Draw structural formulas for the following. (only carbons are usually shown for simplicity in my drawing program.) a. 2,3,5,6-tetramethyloctane C C C C C C C C C C C C b. cis-3,4-dimethyl-3-hexene C C C C C C C C c. 1-ethyl-3-methylcycloheptane CH3CH2 CH3 d. 4,4-dimethyl-2-pentyne C C C C C C C e. 6-methyl-2,4-nonadiene C C C C C C C C C C f. ethylcyclopentane CH2CH3 g. 2,3-dimethyl-1,3-butadiene C C C C C C 7 5. Draw and name 12 isomers that have the formula C6H12. C C C C C C C C 1-hexene cyclohexane C C C C 3-hexene C C C C C C C C C 2-methyl-1-pentene C C C C C C C C C C C C 3-methyl-1-pentene C C C C C C C 4-methyl-1-pentene C 2-hexene C C C C C C C C C 2-methyl-2-pentene C C C C 2,3-dimethyl-1-butene C C C C 3,3-dimethyl-1-butene C C C C C C Cl → CH3CHCH3 Br Br b. CH3CH=CHCH3 + Br2 → CH3CHCHCH3 c. CH3C≡CH + 2 HBr → H3C-CBr2-CH3 d. CH3C≡CCH3 + 2 F2 → CH3CF2CF2CH3 Cl Cl e. 1,3-cyclohexadiene + excess chlorine gas → Cl Cl CH3 Cl AlCl3 f. 1,4-dimethylbenzene + chlorine gas → + HCl CH3 8 C 2,3-dimethyl-2-butene 6. Complete and balance the following. a. CH3CH=CH2 + HCl C C C 4-methyl-2-pentene 3-methyl-2-pentene C C C C 7. Name the following. CH2CH2 a. OH f. CH3 CH3CHCH2CH Br Br 1,2-dibromoethane CH3 4-methyl-2-pentanol O b. CH3CHCH2CH3 g. CH3CCH2CHCH3 NH2 2-aminobutane CH3 4-methyl-2-pentanone c. CH3 h. CH3 HC CH3CHCH2CHCHCH3 CCH2CHCH2CH3 4-methyl-1-hexyne CH2CH3 CH3 2,3,5-trimethylheptane CH3 d. CH3CH i. CHCH2CCH3 1,3-cyclopentadiene CH3 5,5-dimethyl-2-hexene O e. CH3 j. CH3CH2CHCH O CH3CH2CHCH2COH 3-methylpentanoic acid CH3 2-methylbutanal 8. Draw structural formulas for the following: b trans-3-hexene a. 3-hexanone O . CH3 CH3 CH2 C CH2 CH2 CH3 d. propylbutanoate O CH3 CH2 CH2 C C H e . O CH2 CH2 CH3 g. 2-pentyne CH3 CH2 C CH2 CH3 H CH2 CH CH CH CH2 CH3 1,2,3-triethylcyclohexane CH2CH3 CH3CH2 9 I CH3 CH3 CH3 CH3 CH3CH2 iodobenzene C 2,3,4-trimethylhexane CH3 h . C c . f. 3-methyloctanal CH3 O CH3 CH2 CH2 CH2 CH2 CH CH2 C H i. butylpropanoate j. the fat formed by hexanoic acid O CH3 CH2 C O O CH2 CH2 CH2 CH3 CH2 O C CH2CH2CH2CH2CH3 CH O C CH2CH2CH2CH2CH3 CH2 O O C CH2CH2CH2CH2CH3 O k. the oxidation product of 2-pentanol O CH3 C CH2 CH2 CH3 9. Write formulas for the products and name all organic compounds in the following I a. CH3C CH2 + HI CH3C CH3 methylpropene CH3 2-iodo-2-methylpropane O b. CH3CH2CHC O H+ OH + CH3OH CH3CH2CHCH2CH3 CH3CH2CHC OCH3 CH3 methyl-2-methylbutanoate CH3 2-methylbutanoic acid c. CH3 [O] ` CH3CH2CCH2CH3 O 3-pentanone OH 3-pentanol Cl d. + Cl2 Cl 1,2-dichlorocyclohexane cyclohexene O e. CH3CH2CH2CH2OH 1-butanol [O] O [O] CH3CH2CH2CH butanal 10 CH3CH2CH2COH butanoic acid reactions: Cl f. CH3CH2C CH + HCl CH3CH2C 1-butyne Cl CH + HCl H Cl 2-chloro-1-butene O CH3CH2C H CH H 2,2-dichlorobutane O g. CH3CH2C O CH3 + methyl propanoate NaOH CH3CH2C O Na sodium propanoate + CH3OH methanol 10. For the following compound, write a complete, expanded structural formula (with all C-H bonds, etc. clearly shown). Also, name the compound. H3C CH2 O CH CH3 C H C CH C C CH C N C C CH3 H C H H H Name: 2-cyano-4-methyl-5-phenyl-3-heptanone 11. In the structure above, the hybridization at the carbon atom of the CN group is sp and the bond angles around that carbon are about 180 degrees. 12. Write chemical formulas for each of the following compounds. You may use partially condensed formulas (e.g. CH3-CH2-OH for ethanol) as long as the correct number of hydrogens are shown on each carbon and the C-C framework and any functional groups are clearly shown. a. aniline NH2 b. acetone O H3C C CH3 (c. "MTBE" (methyl tert-butyl ether) 11 CH3 H3C O C CH3 CH3 d. 4-amino-3-methylpentanal CH3 H3C CH CH CH2 NH2 O C H 13. Consider all possible carbonyl compounds having the formula C4H6O. a. .Write expanded structural formulas for as many carbonyl isomers of C4H6O as you can (there are more than five). (Note: Points will be deducted if the same structure is drawn more than once but bonus points are available for each correct one beyond five!) O H H C CH2 CH CH2 O C H C C H C C H H C C H H CH3 H H cis C O CH3 H C C CH2 H H O C C O H C CH3 O H H O C trans C O H C C H H CH CH2 H H C C O H3C C CH3 C CH2 CH3 CH3 H O C C C H CH3 H b..One of the above carbonyl isomers (call it compound A) can be cleanly converted in a twostep sequence of reactions to 1,3-butadiene (compound C). Which carbonyl isomer is compound A? Write complete structural formulas for compounds A, B, and C in the reaction sequence below. A H2 B H+ C ∆ 12 O H C CH2 OH H2 CH CH2 H2C CH2 A H+ H2C CH CH CH2 B ∆ CH CH2 C 14. Write complete, systematic names for: 2-cyano-4-methyl-3-heptene 4-phenylhexanal 2-butyl benzoate 5-ethyl-4-methyl-2-octanol 15. Write complete, specific structural formulas for all of the organic reactants and products in each reaction. an ester O CH3 C O NaOH sodium acetate O CH2CH3 CH3 CH C + O- Na+ + 3-pentanol OH CH3 CH2 CH CH2 CH3 CH2CH3 2-hexyne CH3 C C CH2CH2CH3 H2 cis-2-hexene an alcohol OH H H H H2 H2O C CH3 H2O CH3 C CH2CH2CH3H C CCH2CH2CH3 H H 16. For the following compound, write a complete expanded structural formula (with all C-H bonds, etc. clearly shown). Also, name the compound. O 4-ethyl-2-methyl-5-phenyl-3-heptanone 13