Folder test bank is orgo chapter 6

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Alkenes contain the unsaturated C=C functional group which characteristically undergo addition reactions.
This is driven by the conversion of the weaker π bond into 2 new, stronger σ bonds.
The reactions of alkenes can seem a little bewildering as a wide variety of reagents undergo this type of reaction providing access to products with various regioselectivities and stereoselectivities depending on the reagent and / or reaction conditions, but ultimately on the mechanism by which the reaction occurs.
There are potentially 3 factors associated with each of the addition reactions of alkenes:
• overall transformation (i.e. C=C to what functional group)
• regioselectivity (provided the two atoms that add are different)
• stereoselectivity (most easily revealed with cyclic alkenes

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Folder test bank is orgo chapter 6

  1. 1. Chapter 6 Reactions of Alkenes Addition Reactions
  2. 2. • 1. Which one of the following is not a metal catalyst for the hydrogenation of an alkene? • • • • A. B. C. D. Pd Pt Na Ni
  3. 3. • 2. What is(are) the product(s) in the Pdcatalyzed hydrogenation of 1,2dimethylcyclopentene? • A. trans-1,2-dimethylcyclopentane • B. cis-1,2-dimethylcyclopentane • C. a mixture of trans and cis-1,2dimethylcyclopentane • D. 1,1-dimethylcyclopentane
  4. 4. • 3. Which of the following alkenes is expected to have the highest heat of hydrogenation? • • • • A. B. C. D. 1-pentene trans-2-pentene cis-2-pentene 2-methyl-2-butene
  5. 5. • 4. Which alkene below is thermodynamically the most stable? • • • • A. B. C. D. 1-hexene trans-3-hexene cis-3-hexene 2-methyl-2-pentene
  6. 6. • 5. The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as platinum, occurs via • • • • • A. B. C. D. syn addition. anti addition. Markovnikov addition. anti-Markovnikov addition.
  7. 7. • 6. The product(s) in the following reaction is(are) • • • • A. B. C. D. only trans-1-4-dimethylcyclohexane. only cis-1-4-dimethylcyclohexane. both trans and cis-1-4-dimethylcyclohexane. methylcyclohexane.
  8. 8. • 7. What is the major product of the following reaction? • • • • A B C D A. B. C. D.
  9. 9. • 8. Predict which of the following alkenes reacts the fastest with HCl? • • • • A. B. C. D. CH3CH2CH2CH2CH=CH2 cis-CH3CH2CH=CHCH2CH3 trans-CH3CH2CH=CHCH2CH3 (CH3)2C=CHCH2CH3
  10. 10. • 9. Which reagent(s) below would work best in converting 2-methyl-2-hexene to 2-methyl-3hexanol? • • • • • A. B. C. D. (1) H2SO4 (2) H2O 50% H2SO4/H2O (1) BH3/THF (2) H2O2, NaOH Br2/H2O
  11. 11. • 10. The hydroboration-oxidation reaction can be characterized as the ___________________ to an alkene. • • • • • A. B. C. D. anti-Markovnikov syn addition of water anti-Markovnikov anti addition of water Markovnikov syn addition of water Markovnikov anti addition of water

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