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 9, Problem 9.60P
Another important pattern in
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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.
Using your reaction roadmap as a guide, show how to convert ethylene into 1-butene.
All of the carbon atoms of the target molecule must be derived from ethylene. Show all
intermediate molecules synthesized along the way.
Ethylene
1-Butene
10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look
at the functional group PATTERN present in the molecule, including stereochemistry.
♡
Br
Br
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 9.1PCh. 9.3 - Prob. 9.2PCh. 9.3 - Prob. 9.3PCh. 9.3 - Prob. 9.4PCh. 9.4 - Prob. 9.5PCh. 9.5 - Predict the -elimination product(s) formed when...Ch. 9.7 - Prob. 9.7PCh. 9.9 - Predict whether each reaction proceeds...Ch. 9.9 - Prob. AQCh. 9.9 - Prob. BQ
Ch. 9.9 - Prob. CQCh. 9.9 - Prob. DQCh. 9.10 - Prob. 9.9PCh. 9 - Prob. 9.10PCh. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Treatment of 1-aminoadamantane, C10H17N, with...Ch. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Attempts to prepare optically active iodides by...Ch. 9 - Draw a structural formula for the product of each...Ch. 9 - Prob. 9.23PCh. 9 - Alkenyl halides such as vinyl bromide, CH2=CHBr,...Ch. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Show how you might synthesize the following...Ch. 9 - Prob. 9.29PCh. 9 - 1-Chloro-2-butene undergoes hydrolysis in warm...Ch. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Solvolysis of the following bicyclic compound in...Ch. 9 - Which compound in each set undergoes more rapid...Ch. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Draw structural formulas for the alkene(s) formed...Ch. 9 - Prob. 9.38PCh. 9 - Following are diastereomers (A) and (B) of...Ch. 9 - Prob. 9.40PCh. 9 - Elimination of HBr from 2-bromonorbornane gives...Ch. 9 - Which isomer of 1-bromo-3-isopropylcyclohexane...Ch. 9 - Prob. 9.43PCh. 9 - Prob. 9.44PCh. 9 - Draw a structural formula for the major organic...Ch. 9 - When cis-4-chlorocyclohexanol is treated with...Ch. 9 - Prob. 9.47PCh. 9 - The Williamson ether synthesis involves treatment...Ch. 9 - The following ethers can, in principle, be...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 9 - Prob. 9.52PCh. 9 - Prob. 9.53PCh. 9 - Prob. 9.54PCh. 9 - Write the products of the following sequences of...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.59PCh. 9 - Another important pattern in organic synthesis is...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - Prob. 9.64P
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- Describe how 1-ethylcyclohexanol can be prepared from cyclohexane. You can use any inorganic reagents, any solvents, and any organic reagents as long as they contain no more than two carbons.arrow_forwardAcid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol oxygen to form an oxonium ion. Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction. н н :бн н Нас. Нас. CHз CH3 ČH3 CH3 3-methyl-2-butanol an oxonium ion Major Product Minor Product Minor Productarrow_forwardProvide the major organic product of the following reaction. but-1-yne 1) Sia₂BH 2) H₂O₂, OH What is it called when an enol converts to a keto? A) Keto-enol isomerism B) Keto-enol tater tot-ism C) Keto-enol conversion D) Keto-enol tautomerismarrow_forward
- Show how to convert ethylene to these compounds. (a) Ethane (b) Ethanol (c) Bromoethane (d) 2-Chloroethanol (e) 1,2-Dibromoethane (f) 1,2-Ethanediol (g) Chloroethanearrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexane into hexanedial. Show all reagents and all molecules synthesized along the way.arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-bromopropane and carbon dioxide into 4-propyl-4-heptanol. You must use 1-bromopropane and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forward
- Using your reaction roadmap as a guide, show how to convert butane into 2-butyne. Show all reagents and all molecules synthesized along the way.arrow_forwardUsing your reaction roadmaps as a guide, show how to convert ethylene into 2-methyl-1,3-dioxolane. You must use ethylene as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forwardUsing your reaction roadmaps as a guide, show how to convert propane into propyl propanoate. You must use propane as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward
- 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).arrow_forwardUsing your reaction roadmap as a guide, show how to convert the starting trans-alkene to the cis-alkene in high yield. Show all intermediate molecules synthesized along the way.arrow_forwardShow how to prepare each compound from 1-heptene. a. 1,2-Dichloroheptane b. 1-Heptyne c. 1-Heptanol d. 2-Octyne e. cis-2-Octene f. trans-2-Octenearrow_forward
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