tb10 - ChaDter 10- OrHanohalides Give the name for each of...

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Chapter 10: Organohalides ChaDter 10- OrHanohalides Give the name for each of the following alkyl halides. 1. a a I I H-C-C-H I I a H Answer: 1,1,2-trichloroethane 2. CHl3 Answer: triiodomethane F a I I 3. F- C- C- H ' Halothane I I F Br Answer: 2-bromo- 2-chloro-l, I,l-trifluoroethane 4. CH2Cl2 Answer: dichloromethane Draw structures corresponding to these names. s. 3-iodopropene Answer: ~I 6. trans-I-chloro-3-sec-butylcyclohexane Answer: °"'1 7. 1,2-dichloro-I,1 ,2,2-tetrafluoroethane (Cryofluorane) Answer: a CI I I F-C-C-F I I F F 80
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8. (S)-2-bromobutane Answer: H Br ~ To answer the following questions consider the reaction below: ~ I (CH3)3COCI. V 40°C c0 ~a 65% 25% 10% 9. When propylbenzene reacts with tert-butylhypochlorite three monochlorinated products are formed in the ratios indicated. Calculate a reactivity order for each type of hydrogen atom in propylbenzene. Answer: Ar - CH2- = 65% + 2 = 32j% product + 33 = 9.85 -CHr = 25% + 2 = 12j% product + 33 = 3.8 -CHr = 10% + 3 = 33% product + 3.3= 1 Therefore the Relative Reactivity for CH3:CH2:ArCH2 is 1:3.8:9.85. 10. The reaction of propylbenzene with tert-butylhypochlorite proceeds by a radical substitution pathway. Draw the structure ofthe radical intermediate leading to each product. Answer: . ~ / U:(CHW= . (JY ~~. Test Itemsfor McMurry's Organic Chemistry, Seventh Edition . ~ .()( .~a 81
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11. Based on your answers to the two questions above explain why (I -chloropropyl)benzene is the major product of this reaction. Answer: In question 9 we calculated that the hydrogens next to the aryl group, the benzylic hydrogens, are about 2.5 times more reactive than the methylene hydrogens and about 10 times more reactive than the methyl hydrogens. This means that the benzylic radical is more stable than a 2
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This note was uploaded on 03/10/2012 for the course PHYS 121 taught by Professor Staff during the Spring '08 term at CUNY Queens.

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tb10 - ChaDter 10- OrHanohalides Give the name for each of...

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