1. The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene a. Draw the structure of 1,2-dimethylcyclohexene b. Show a mechanism for the formation of this alkene product c. Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reaction

1. The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene a. Draw the structure of 1,2-dimethylcyclohexene b. Show a mechanism for the formation of this alkene product c. Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reaction

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.31P: When 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation...

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The alkene mixture obtained on the dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene Draw the structures of 1,2-dimethylcyclohexene Show the mechanism for the formation of this alkene product Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reaction
A compound X of molecular formula C7H14 when hydrogenated produces 2,4-dimethylpentane and when hydroborated the obtained alcohol is 2,4-dimethyl-1-pentanol. a. What is the structure of X? b. If X is reacted with H2O catalyzed by H2SO4, what product is obtained? Write the structure, give the name, and write the complete mechanism, step by step of this reaction, in such a way as to explain the formation of the compound (DO NOT FORGET THE CORRECT USE OF ARROWS!).
4-methyl-3-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH; (for hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. If there is more than one alkene that can be used for a given method, draw all of them. If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. • Separate structures with + signs from the drop-down menu.
When 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).
What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2- butanol? Loss of a b-hydrogen from the carbocation to form an alkene. Protonation of the alcohol to form an oxonium ion. Loss of water from the oxonium ion to form a carbocation. The simultaneous loss of a B-hydrogen and water from the oxonium ion.
4. Show the steps and reagents needed to transform 1-propyne into 2-methylheptane. You may use any alkyl halide and inorganic reagents. 1-propyne → 2-methylheptane
Acid-catalyzed dehydration of 3-methyl-2-pentanol gives three alkenes: 3-methyl-1-pentene, 3-methyl-2-pentene, and 3-methylenepentane. Draw the structure of the carbocation intermediate leading to the formation of 3-methyl-2-pentene.
10) For the reaction between isopropyl 1-propyl (or 'n-propyl') ether and HBr, which type of reaction best matches the expected products? A) Acid-catalyzed dehydration B) Nucleophilic substitution reaction C) Ether cleavage reaction D) Nucleophilic addition-elimination reaction
1. List the following alcohols in order of increasing reactivity (least reactive first) toward dehydration with concentrated sulfuric acid. a) CH,CHOHCHз b) (CH3CH2)3COH c) CH3CH2OH 2. Complete the following equations for dehydration reactions. List all the alkenes that could be formed. OH OH H* H* a) (CH;CH2),CCH3- b) ningla s bru
Show the structures of all possible acid-catalysed dehydration products of the following. Where more than one alkene is possible, indicate which one will be formed in the largest amount. a) Cyclohexanol b) 2-butanol c) 1-methylcyclopentanol
Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. Q.) 1-Methylcyclohexene
3. Complete the chemical equations for the following reactions. Draw the structure (condensed structural formulas) for the dominant product and write the names of the reactants and products (organic compounds only.) d) CHy Name reactant: Name product: e) CH=C-CH + 2 HBr 4-Cて。 Name reactant: Name product: