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AHW3 - CHEMISTRY 4210 Spring 2010 HW-Chapter3 Name SID 1 An...

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Page 1 CHEMISTRY 4210, Spring 20 1 0 HW-Chapter3 Name: _____________________________ SID:__________________ 1. An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane. Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic product. The structure of the alkene is: A) B) C) D) E) Ans: B
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Page 2 2. What is the structure of the compound Z that yields 2 mol of formaldehyde and 1 mol of upon ozonolysis followed by treatment with zinc in acetic acid?
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Page 3 3. Compound, C, has the molecular formula C 7 H 12. On catalytic hydrogenation, 1 mol of C absorbs 1 mol of hydrogen and yields a compound with the molecular formula C 7 H 14 . On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only: The structure of C is: 4. Compound X has the molecular formula C 6 H 10 . X decolorizes bromine in carbon tetrachloride. X also shows IR absorption at about 3300 cm -1 . When treated with excess hydrogen and a nickel catalyst, X yields 2-methylpentane. The most likely structure for X is:
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Page 4 5. An unknown compound, A, has the molecular formula C 7 H 12 . On oxidation with hot aqueous potassium permanganate, A yields CH 3 CH 2 COOH and . Which of the following structures best represents A? A) B) C) D) E) Ans: C 6. An alkene, X, with the formula C 7 H 10 adds one mole of hydrogen on catalytic hydrogenation. On treatment with hot basic KMnO 4 followed by acidification, X yields Which is a possible structure for X?
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Page 5 7. An optically active compound, Y, with the molecular formula C 7 H 12 gives a positive test with cold dilute KMnO 4 and shows IR absorption at about 3300 cm -1 . On catalytic hydrogenation, Y yields Z(C 7 H 16 ) and Z is also optically active. Which is a possible structure for Y?
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Page 6 8. One mole of an optically active compound, X, with the molecular formula C 6 H 8 reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved. X also exhibits IR absorption at approximately 3300 cm -1 . Which is a possible structure for X?
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Page 7 9. An alkene with the molecular formula C 8 H 14 is treated with ozone and then with zinc and acetic acid. The product isolated from these reactions is What is the structure of the alkene? A) I B) II C) III D) IV E) V Ans: C
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