Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 6, Problem 6.47P

Describe the stereochemistry of the bromohydrin formed in each reaction (each reaction is stereospecific).

  1. (a) cis-3-Hexene + Br2/H2O
  2. (b) trans-3-Hexene + Br2/H2O
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Draw the structure of (E,6R) 6-methoxy-4-hepten-2-one. Give the IUPAC name of this compound, including stereochemistry. Draw the most stable chair conformation of (cis) 1,3-isobutylcyclohexane. H HC=CCH₂ CH2CH3 EN(CH3)2 -CN(CH3)2
10. Write out the mechanism (intermediate/transition state) for this reaction; indicate stereochemistry in product. H3C CH₂OH CH3 SN1 H
Write "most" under the member of each trio which is most stable. Write "least under the member of each trio which is least stable. b) Draw a Fischer projection of a pair of enantiomers with three chiral carbons. Which of these two would you expect to be more soluble in water? Why? 1-butanol 1-heptanol Which of these two would you expect to have the higher boiling point? Why? hexyl methyl ether 1-heptanol

Chapter 6 Solutions

Organic Chemistry

Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Prob. 6.53PCh. 6 - Prob. 6.54P
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