Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 8.SE, Problem 30MP
Provide the mechanism and products for the acid-catalyzed
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
When 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of
substitution and elimination products is obtained. Provide structures for all possible
products, writing [not drawing] the name of the mechanism by which each one is
formed.
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.
Br
Brz
CH3
CH3
H3C
CH2CI2
H3C
Br
Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion.
The reaction occurs in an anhydrous solvent such as CH,Cl).
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes,
the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br:
:Br:
.CH3
H3C
H3C
CH3
Br:
Chapter 8 Solutions
Organic Chemistry
Ch. 8.1 - Prob. 1PCh. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3PCh. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5PCh. 8.3 - Prob. 6PCh. 8.4 - Prob. 7PCh. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9PCh. 8.5 - What alkenes might be used to prepare the...
Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - What products would you expect from the following...Ch. 8.10 - Prob. 18PCh. 8.10 - Prob. 19PCh. 8.13 - Prob. 20PCh. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Prob. 23VCCh. 8.SE - Prob. 24VCCh. 8.SE - Prob. 25VCCh. 8.SE - Prob. 26MPCh. 8.SE - Prob. 27MPCh. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - Prob. 29MPCh. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Prob. 32MPCh. 8.SE - Prob. 33MPCh. 8.SE - Prob. 34MPCh. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Prob. 40MPCh. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Prob. 42APCh. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Prob. 44APCh. 8.SE - Prob. 45APCh. 8.SE - Prob. 46APCh. 8.SE - Prob. 47APCh. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Prob. 49APCh. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - Prob. 53APCh. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Prob. 55APCh. 8.SE - Prob. 56APCh. 8.SE - Prob. 57APCh. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - Prob. 59APCh. 8.SE - Prob. 60APCh. 8.SE - Prob. 61APCh. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Prob. 63APCh. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Prob. 65APCh. 8.SE - Prob. 66APCh. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Prob. 68APCh. 8.SE - Prob. 69APCh. 8.SE - Prob. 70APCh. 8.SE - Prob. 71APCh. 8.SE - Prob. 72AP
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
- Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardEnamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forwardIt is not uncommon for organic chemists to prepare acetals by an exchange-type process known as transacetalization. Predict the product(s) and show the mechanism for the transacetalization reactions below.arrow_forward
- When 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two productsare formed. Propose a mechanism that accounts for both of these productsarrow_forwardWrite the products of the following Cope rearrangements; pay particular attention to the stereochemistry in the products. Predict which is preferred.arrow_forwardPlease give the main substitution product for each of the following reactions, and indicate the dominant mechanism: (a) 1-bromopropane + NaOCH3 → (b) 3-bromo-3-methylpentane + NaOC2H5 →arrow_forward
- 2,3-Dimethylbutane reacts with bromine in the presence of light to give a mono brominated product. The further reaction gives a good yield of a dibrominated product. Predict the structures of these products, and propose a mechanism for the formation of the mono brominated product.arrow_forwardGive a mechanism that accounts for the organic products of this reaction. Your mechanism must include a transition state that accounts for the stereochemistry of the product and/or reactant. Redraw the reagents as needed. CI OH NaOH, DMSO + NaClarrow_forwardPredict the products of conjugate (Michael) additions, and show how to use thesereactions in syntheses. Show the general mechanism of the Robinson annulation,and use it to form cyclohexenone ring systems.arrow_forward
- Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forwardPredict the coupling products of organometallic substitutions, and use them in syntheses.arrow_forwardSuggest reagents and mechanism for this reaction. H H Narrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License