Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 8, Problem 8.46P
Interpretation Introduction
Interpretation:
The racemization that occurs when
Concept introduction:
When the
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(R)-2-iodo-3-methylbutane is treated with sodium bromide in acetone. Select all products that are formed.
2-methylbutan-1-ol
2-methylbutan-2-ol
3-methylbut-1-ene
(R)-3-methyl-2-butanol
2-methylbut-2-ene
O (S)-2-bromo-3-methylbutane
When (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.
When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone.
Write the mechanism for each of the two reactions.
Chapter 8 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 8 - Prob. 8.1PCh. 8 - Prob. 8.2PCh. 8 - Prob. 8.3PCh. 8 - Prob. 8.4PCh. 8 - Prob. 8.5PCh. 8 - Prob. 8.6PCh. 8 - Prob. 8.7PCh. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10P
Ch. 8 - Prob. 8.11PCh. 8 - Prob. 8.12PCh. 8 - Prob. 8.13PCh. 8 - Prob. 8.14PCh. 8 - Prob. 8.15PCh. 8 - Prob. 8.16PCh. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Prob. 8.20PCh. 8 - Prob. 8.21PCh. 8 - Prob. 8.22PCh. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - Prob. 8.25PCh. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - Prob. 8.30PCh. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - Prob. 8.34PCh. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - Prob. 8.38PCh. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - Prob. 8.41PCh. 8 - Prob. 8.42PCh. 8 - Prob. 8.43PCh. 8 - Prob. 8.44PCh. 8 - Prob. 8.45PCh. 8 - Prob. 8.46PCh. 8 - Prob. 8.47PCh. 8 - Prob. 8.48PCh. 8 - Prob. 8.49PCh. 8 - Prob. 8.50PCh. 8 - Prob. 8.51PCh. 8 - Prob. 8.52PCh. 8 - Prob. 8.53PCh. 8 - Prob. 8.54PCh. 8 - Prob. 8.55PCh. 8 - Prob. 8.56PCh. 8 - Prob. 8.57PCh. 8 - Prob. 8.58PCh. 8 - Prob. 8.59PCh. 8 - Prob. 8.60PCh. 8 - Prob. 8.61PCh. 8 - Prob. 8.62PCh. 8 - Prob. 8.63PCh. 8 - Prob. 8.64PCh. 8 - Prob. 8.65PCh. 8 - Prob. 8.66PCh. 8 - Prob. 8.67PCh. 8 - Prob. 8.68PCh. 8 - Prob. 8.69PCh. 8 - Prob. 8.70PCh. 8 - Prob. 8.71PCh. 8 - Prob. 8.72PCh. 8 - Prob. 8.73PCh. 8 - Prob. 8.74PCh. 8 - Prob. 8.75PCh. 8 - Prob. 8.76PCh. 8 - Prob. 8.1YTCh. 8 - Prob. 8.2YTCh. 8 - Prob. 8.3YTCh. 8 - Prob. 8.4YTCh. 8 - Prob. 8.5YTCh. 8 - Prob. 8.6YTCh. 8 - Prob. 8.7YTCh. 8 - Prob. 8.8YTCh. 8 - Prob. 8.9YTCh. 8 - Prob. 8.10YTCh. 8 - Prob. 8.11YTCh. 8 - Prob. 8.12YTCh. 8 - Prob. 8.13YTCh. 8 - Prob. 8.14YTCh. 8 - Prob. 8.15YTCh. 8 - Prob. 8.16YTCh. 8 - Prob. 8.17YTCh. 8 - Prob. 8.18YTCh. 8 - Prob. 8.19YT
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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardDraw the product when each compound is treated with either (CH3)2CuLi, followed by H2O, or HC≡CLi, followed by H2O.arrow_forwardCan you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst. The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.arrow_forward
- When 2,2-dimethylcyclohexanol is treated with acid, 1,2-dimethylcyclohexene and iso- propylidenecyclopentane are the products obtained. Draw a detailed mechanism that explains this result. CH3 H3O+ CH3 CH3 CH3 OH CH3 CH3 2,2-dimethyl- cyclohexanol 1,2-dimethyl- isopropylidene- cyclopentane cyclohexenearrow_forwardAn allylic alcohol contains an OH group on a carbon atom adjacent to a C − C double bond. Treatment of allylic alcohol A with HCl forms a mixture of two allylic chlorides, B and C. Draw a stepwise mechanism that illustrates how both products are formed.arrow_forwardsingle reaction sequence: a certain ketone undergoes alkylation to give new ketone, when reacted with a base and then an alkylating agent, 1-bromopropane. What is the structure of the final ketone product?arrow_forward
- When 3-methyl-2-butanol is heated with concentrated HBr, a rearranged product is obtained. When 2-methyl-1-propanol reacts under the same conditions, a rearranged product is not obtained. Explain.arrow_forwardExplain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.arrow_forwardWhen cis-2-decalone is dissolved in ether containing a trace of HCI, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. H H HCI cis-2-Decalone trans-2-Decalone Propose a mechanism for this isomerization and account for the fact that the trans iso- mer predominates at equilibrium.arrow_forward
- When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone –arrow_forward2) Suggest a mechanism explaining how the following reaction leads to an acetal, yet no alcohol is present. MeO OMe H* OMe OMearrow_forwardRearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocation is formed—that is, a 1,2-shift occurs as the C − OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as shown. Using this information, draw a stepwise mechanism that shows how CH3CH2CH2CH2OH is dehydrated with H2SO4 to form a mixture of CH3CH2CH = CH2 and the cis and trans isomers of CH3CH = CHCH3. We will see another example of this type of rearrangement in Section 18.5C.arrow_forward
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