Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Videos
Textbook Question
Chapter 6, Problem 6.38P
Reaction of α-pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol.
Of the four possible cis,trans isomers, one is formed in over 85% yield.
- (a) Draw structural formulas for the four possible cis,trans isomers of the bicyclic alcohol.
- (b) Which is the structure of the isomer formed in 85% yield? How do you account for its formation? Create a model to help you make this prediction.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
1. (a) Draw structures of the seven isomeric alkynes of formula C6H10 - (b) Give the IUPAC and derived name of each. (c) Indicate which ones will react with Ag' or Cu(NH3)2.
(a) Alkenes are relatively stable compounds but are more reactive
than alkanes and serve as a feedstock for the petrochemical
industry because they can participate in a wide variety of reactions.
Predict the products obtained from following reaction. Write the chemical
reaction and name the products according to IUPAC system.
(i) the reaction of 3-ethyl-3-methyl-1-pentene with hydrogen
bromide
(ii) the reaction of 3-ethyl-2-pentene with hydrogen bromide
What is the structure of the alcohol produced when 3-methyl-1-pentene undergoes
(a) acid catalyzed hydration
(b) oxymercuration/demercuration
(c) hydroboration/oxidation
Chapter 6 Solutions
Organic Chemistry
Ch. 6.2 - Using the BDE values from Appendix 3, calculate...Ch. 6.3 - Name and draw a structural formula for the product...Ch. 6.3 - Prob. 6.3PCh. 6.3 - Propose a mechanism for the addition of HI to...Ch. 6.3 - Prob. 6.5PCh. 6.3 - Propose a mechanism for the acid-catalyzed...Ch. 6.3 - The acid-catalyzed hydration of...Ch. 6.3 - Complete these reactions. (a) (b)Ch. 6.3 - Draw the structure of the chlorohydrin formed by...Ch. 6.4 - Draw structural formulas for the alkene that gives...
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanolarrow_forward(a) Write a chemical test to distinguish between: (i) Chlorobenzene and Benzyl chloride. (ii) Chloroform and Carbon tetrachloride. (b) Why is methyl chloride hydrolysed more easily than chlorobenzene?arrow_forwardPropose a structural formula for the product(s) when each of the following alkenes is treated with H2O/H,SO4. Why are two products formed in part (b), but only one in parts (a) and (c)? (a) 1-Hexene gives one alcohol with a molecular for- mula of C,H140. (b) 2-Hexene gives two alcohols, each with a molecu- lar formula of C,H140. (c) 3-Hexene gives one alcohol with a molecular for- mula of C6H140.arrow_forward
- Ketene, H2C=C=O, is an important industrial chemical. Predict the products that would be formed when ketene reacts with **hint: Markovnikov addition occurs. (a) ethanol (b) acetic acid (c) ethylamine.arrow_forwardCompounds B and C are hydrocarbons with the structural formulae as shown below. CH, „CH, в (a) Name compounds B and C according to the IUPAC nomenclature. (b) Both B and C can undergo oxidation reaction with the same oxidizing agent. Write chemical equations involved and explain the differences between these two reactions. (c) Name one reaction that converts B to methylcyclohexane.arrow_forward1. (a) Draw the structures of the eight isomeric pentyl alcohols, C3H11OH. (b) Name each by the IUPAC system and by the carbinol system. (c) Label each as primary, secondary, or tertiary, (d) Which one is isopentyl alcohol? tert-Pentyl alcohol? (e) Give the structure of a primary, a secondary, and a tertiary alcohol of the formula C,H13OH.arrow_forward
- Write a complete chemical equation showing reactants, products, and catalysts needed(if any) for the following reaction and (2) Draw and name the organic compound found inevery reaction.(Use condensed structural formula) (A) Reaction of cis-3,3-Dimethyl-4-propylocta-1,5-diene with two mole of HBr(B) Reaction of trans-1-Bromo-3-chlorocyclopentane with potassium hydroxide(C) Formation of Gilman reagent using isopropyl bromidearrow_forward2) Provide structures for the following compounds: a) ethyl acetate b) Pentanoic acidarrow_forwardAnswer true or false. (a) Alkenes and alkynes are nonpolar molecules. (b) The physical properties of alkenes are similar to those of alkanes of the same carbon skeletons. (c) Alkenes that are liquid at room temperature are insoluble in water and when added to water, will float on water.arrow_forward
- (1) Write a complete chemical equation showing reactants, products, and catalysts needed (if any) for the following reaction and (2) Draw and name the organic compound found in every reaction. (a) Complete hydrogenation of 2-Methylhexa-1,5-diene (b) Complete halogenation (Br2) of 3-Ethyl-2,2-dimethylhept-3-ene (c) Reaction of (4E)-2.4-Dimethylhexa-1,4-diene with a mole of water (d) Reaction of cis-3,3-Dimethyl-4-propylocta-1,5-diene with two mole of HBr (e) Reaction of trans-1-Bromo-3-chlorocyclopentane with potassium hydroxide (f) Formation of Gilman reagent using isopropyl bromide (g) Ozonolysis of 3,3-Dimethyloct-4-yne (h) Complete halogenation (Cl2) of 3-Ethyl-5-methyl-1,6,8-decatriyne (i) Partial hydrogenation using Lindlar's Catalyst 2,2,5,5-Tetramethylhex-3-yne (i) Reaction of 3.4-Dimethylcyclodecyne with sodium amidearrow_forwardTRUE OR FALSE (a) Both ethylene and acetylene are planar molecules. (b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism. (c) Cis-trans isomers have the same molecular formula but a different connectivity of their atoms. (d) Cis-2-butene and trans -2-butene can be interconverted by rotation about the carbon–carbon double bond. (e) Cis-trans isomerism is possible only among appropriately substituted alkenes. (f) Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers. (g) Cyclohexene can exist as a pair of cis-trans isomers. (h) 1-Chloropropene can exist as a pair of cis-trans isomers.arrow_forwardWrite structural formulas for compounds that meet the following descriptions:(a) An alkene, C6H12, that cannot have cis–trans isomersand whose longest chain is 5 carbons long(b) An alkene with a chemical formula of C10H12 that hascis–trans isomers and contains a benzene ring.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY