Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 8, Problem 8E
Interpretation Introduction
Interpretation: The complete mechanism that includes the intermediate and most likely product of given reactants with
Concept introduction:
The product formed is governed by Markovnikov’s Rule. Rule suggests that negative part of halo acid HX must go to the carbon that has more alkyl substituents or less
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Students have asked these similar questions
Draw the major organic product formed by reaction of 2-hexyne with the following reagent: H₂O in H₂SO4
/ HgSO4.
• Consider E/Z stereochemistry of alkenes.
• In cases where there is more than one answer, just draw one.
• If no reaction occurs, draw the organic starting material.
МЕСНANISMS
1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed
opening of the epoxide ring to form two different products.
> Using ethanol as the solvent and an appropriate acid, show the steps in the acid
catalyzed mechanism, writing structures for all products of the steps. Circle the major
product(s).
> Using ethanol as the solvent and an appropriate base, show the steps in the base-
catalyzed mechanism, writing structures for all products of the steps. Circle the major
product(s).
1,2-epoxy-1-methylcyclopentane
CH3
4. Use the reactant below to perform two separate reactions. Give the mechanism(s) and product(s) for each
reaction. Show stereochemistry and be clear in your work. Use chair form.
KOEt, EtOH
t-Bu
||||
H3O+
Chapter 8 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 8 - Prob. 1CTQCh. 8 - Prob. 2CTQCh. 8 - Prob. 3CTQCh. 8 - Prob. 4CTQCh. 8 - Prob. 5CTQCh. 8 - Prob. 6CTQCh. 8 - Prob. 7CTQCh. 8 - Prob. 8CTQCh. 8 - Prob. 9CTQCh. 8 - Prob. 10CTQ
Ch. 8 - Draw the products that result from the electron...Ch. 8 - Prob. 12CTQCh. 8 - Draw the products that would result if the arrow...Ch. 8 - Prob. 14CTQCh. 8 - What information (if any) from the following...Ch. 8 - Prob. 16CTQCh. 8 - Prob. 17CTQCh. 8 - The reactants, intermediates, final products, and...Ch. 8 - Prob. 19CTQCh. 8 - Prob. 20CTQCh. 8 - Prob. 21CTQCh. 8 - Prob. 22CTQCh. 8 - Explain how you can tell from the energy diagram...Ch. 8 - Explain why the following mechanism for hydration...Ch. 8 - Prob. 25CTQCh. 8 - Prob. 26CTQCh. 8 - Prob. 27CTQCh. 8 - Prob. 28CTQCh. 8 - Prob. 29CTQCh. 8 - Prob. 30CTQCh. 8 - Prob. 31CTQCh. 8 - The hydration above is one of a family of...Ch. 8 - Prob. 33CTQCh. 8 - Which statement is false? a. A mechanistic step...Ch. 8 - Prob. 35CTQCh. 8 - Prob. 36CTQCh. 8 - Prob. 37CTQCh. 8 - Draw the complete mechanism including the...Ch. 8 - Prob. 2ECh. 8 - Explain why ethene does not react with HX ( X=Cl ,...Ch. 8 - Draw the complete mechanism of each pair of...Ch. 8 - Prob. 5ECh. 8 - Prob. 6ECh. 8 - Prob. 7ECh. 8 - Prob. 8ECh. 8 - Prob. 9ECh. 8 - Prob. 10ECh. 8 - Prob. 11ECh. 8 - Prob. 12ECh. 8 - Prob. 15ECh. 8 - A student proposes the following reaction...Ch. 8 - Prob. 17ECh. 8 - Prob. 18ECh. 8 - Prob. 19E
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Similar questions
- Draw the major organic product formed by reaction of 2-hexyne with the following reagent: BH3 followed by CH3COOH. . Consider E/Z stereochemistry of alkenes. In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material.arrow_forwardAlkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*arrow_forward2- Mention the product of a nucleophilic substitution reaction of (S)-2-bromohexane with acetate ion, CH3CO2- Assume that inversion of configuration occurs, and show the chemistry of both the reactant and product. 3- Draw the mechanism of the SN2 Reaction. Show the correct directions of the arrows, and all reagents. 4- Draw the mechanism of the SN1 Reaction. Show the correct directions of the arrows, and all reagents. 5- Draw the mechanism of the E2 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 6- Draw the mechanism of the E1 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 7- Mention the product formed in an SN2 reaction between 1-bromobutane and NaI. 8- Rank the following compounds in order of their expected reactivity toward SN2 reaction: CH3Br, CH3OTos, (CH3)2CHCl. 9- Explain Grignard Reagents in details with one example. 10- Mention how a halogen substituent can be replaced by a deuterium atom…arrow_forward
- (b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, andthe products. Note that the initial product is the salt of an amine (RNH3+ Br - ), which is deprotonated by the excess ammonia to give the amine.arrow_forwardDraw the major organic product formed by reaction of 2-hexyne with the following reagent: H2/ Lindlar catalyst. Consider E/Z stereochemistry of alkenes. In cases where there is more than one answer, just draw one. If no reaction occurs, draw the organic starting material.arrow_forwardKindly answer question a & barrow_forward
- CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardPlease Show reaekson and don't use hend raitingarrow_forwardreaction of this alkene to the different reagents written above and below the arrowsarrow_forward
- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, 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 CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardFirst Writedown which reaction it is? SN1, SN2, E1? Write a stepwise mechanism for the following reactions showing ALL intermediates. Use curved arrows to symbolize the flow of electrons to show how each of the intermediates and product are formed. Show all necessary lone pairs and formal charges.arrow_forwardAn ether can be prepared from an alkene and an alcohol by electrophilic addition, as shown in the reaction below. H+ CH₂CH₂OH Complete the mechanism for this reaction by adding curved arrows and products. Add steps as necessary, and be sure to include lone pairs and charges where relevant.arrow_forward
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