Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 5, Problem 41P
The reaction of
![Chapter 5, Problem 41P, The reaction of 2,2-dimethyl-1-propanol [(CH3)3CCH2OH], also known by the common name neopentyl](https://content.bartleby.com/tbms-images/9780073511214/Chapter-5/images/11214-5-41p-question-digital_image40.png)
Give a mechanistic explanation for these observations.
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The reaction of 2,2-dimethyl-1-propanol [(CH3)3CCH2OH], also known by the common name neopentyl alcohol, with HBr is very slow and gives 2-bromo-2-methylbutane as the major product.Give a mechanistic explanation for these observations.
Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide.
Draw the structure of the expected organic product of the reaction of iodoethane with the following alkoxide ion:
H3C
CH3
+
Na
You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
Do not include lone pairs in your answer. They will not be considered in the grading.
• Do not include counter-ions, e.g., Na", I, in your answer.
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The reaction of 2,2-dimethyl-1-propanol with HBr is very slow and forms 2-bromo-2-methylbutane as the main product Come up with a mechanism to explain these observations
Chapter 5 Solutions
Organic Chemistry - Standalone book
Ch. 5.1 - Prob. 1PCh. 5.1 - Prob. 2PCh. 5.1 - Many compounds contain more than one functional...Ch. 5.2 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.4 - Classify the isomeric C4H10O alcohols as being...Ch. 5.5 - Bromine is less electronegative than chlorine, yet...Ch. 5.6 - Prob. 8PCh. 5.7 - Prob. 9PCh. 5.8 - Prob. 10P
Ch. 5.8 - Prob. 11PCh. 5.9 - Carbocations are key intermediates in petroleum...Ch. 5.9 - Prob. 13PCh. 5.9 - Prob. 14PCh. 5.11 - Prob. 15PCh. 5.13 - Prob. 16PCh. 5.14 - For the reaction of a primary alcohol RCH2OH with...Ch. 5.15 - Prob. 18PCh. 5 - Write structural formulas for each of the...Ch. 5 - Prob. 20PCh. 5 - Prob. 21PCh. 5 - Write structural formulas for all the...Ch. 5 - Prob. 23PCh. 5 - Prob. 24PCh. 5 - Epichlorohydrin is the common name of an...Ch. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Prob. 28PCh. 5 - Some of the most important organic compounds in...Ch. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - The reaction of 2,2-dimethyl-1-propanol...Ch. 5 - (a) Assuming that the rate-determining elementary...Ch. 5 - The reaction of 3-tert-butyl-3-pentanol with...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46DSPCh. 5 - Prob. 47DSPCh. 5 - Prob. 48DSPCh. 5 - Prob. 49DSPCh. 5 - Prob. 50DSPCh. 5 - Prob. 51DSPCh. 5 - Prob. 52DSP
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- Under milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sn2 rather than an Sn1 reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Make sure the mechanism includes protonation, Sn2, and deprotonation.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardFollowing is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forward
- Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardBoth cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH3)3 as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanoleliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.arrow_forwardWhen (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation. Predict which of the three alkenes is the major elimination productarrow_forward
- Describe the reaction mechanism for the hydrolysis of 2-bromo-2-methylpropane [CH3C(CH3)2Br] with aqueous hydroxide ions (OH-).arrow_forwardTwo substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forward
- The reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products: (2R)-2-iodo-3-methylpentane and racemic 3-iodo-2-methylpentane. Account for the formation of each of these two products. For each product, you should show how it is formed and what that tells you about the mechanism of that specific reaction.arrow_forwardThe reaction of 2,2-dimethyl-1-propanol with HBr is very slow and forms 2-bromo-2-methylbutane as the main product Propose a mechanism to explain these observationsarrow_forwardn-Pentanol (CH3CH2CH2CH2CH2OH) and 2-methylbutan-2-ol (CH3CH2C(CH3)2OH) are converted to their corresponding alkyl chorides on being reacted with hydrogen chloride. (a) Write out an equation for each reaction (b) Assign each the appropriate symbol (SN1 or SN2) (c) Write a suitable mechanism for each reactionarrow_forward
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