tb14 - Chapter 14 - Coniuf!ated Compounds and Ultraviolet...

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126 Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy Chapter 14 - Coniuf!ated Compounds and Ultraviolet Spectroscopv Draw structures corresponding to each name below. 1. 2-methyl-l,3-butadiene Answer: ~ 2. (2Z,4Z)-hexadiene Answer: F\d Give IUPAC names for the following alkenes: 3. >=« Answer: 2,3,4,5-tetramethyl-2,4-hexadiene 4.~ Answer: (3E)-2-methyl-l,3-pentadiene Circle any conjugated portions in the molecules below. 0 5. ~OCH U3 Answer: OCH3
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6. (:(0 a ~Answer: (0) a ~7. H2C= CH- C- N Answer: €CH-~ 8. H'~ Answer: c;;g CH3 I 9. a c"" CH, Answer: not conjugated Consider the reaction below to answer the following questions: () + HBr A B 10. The nucleophile in this reaction is_: Answer: A 11. The electrophile in this reaction is_: Answer: B Test Items/or McMurry's Organic Chemistry, Seventh Edition ~ Br + () c D 127
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12. The kinetically controlled product in this reaction is - . Answer: D 13. Theproductthat results from 1,4-additionis - . Answer: c 14. Write a stepwise mechanism that accounts for both of the products shown. Show all intermediate structures and electron flow with arrows. Answer: ~ ~ V ~HcJr -'V :~r: -cf t ..0 () ~ H Br "C) :lli: ~ .. 15. This reaction shows the preferred electrophilic addition of HBr to this unsymmetrical alkene. Draw the products of electrophilic addition to the opposite end of the conjugated diene. Answer: 2 4 1~ V3 + HBr Br (r ~ + 16. Electrophilic addition reaction of conjugated dienes that occur at high temperature and/or long reaction times (reversible conditions) are said to be under: a. 1,2- control b. kinetic control c. 1A-control d. thermodynamic control Answer: d 128 Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
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Consider the data given below to answer
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This note was uploaded on 10/10/2011 for the course CHEMISTRY CHM2046 taught by Professor Johnston during the Spring '11 term at University of South Florida - Tampa.

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tb14 - Chapter 14 - Coniuf!ated Compounds and Ultraviolet...

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