Concept explainers
(a)
Interpretation:
The principal organic compound that is expected when
Concept introduction:
The addition reaction of the
Answer to Problem 17.22AP
The principal organic compound that is formed when
Explanation of Solution
The reaction of
Figure 1
The addition of the bromine molecule on the double bond of the alkene takes place to give the dibromo product. The addition of bromine to the double bond is the anti-addition.
The principal organic compound that is formed when
(b)
Interpretation:
The principal organic compound that is expected when
Concept introduction:
The addition reactions of the alkene are very well known reactions. The electron density on the alkene double bond makes it nucleophilic. The alkene undergoes varieties of addition reaction via different mechanisms.
Answer to Problem 17.22AP
The principal organic compound that is formed when
Explanation of Solution
The reaction of
Figure 2
The reaction of an alkene with N-bromosuccinimide in the presence is the free-radical reaction. In this reaction, allylic bromination is observed instead of an addition to the alkene. The N-bromosuccinimide acts as radical initiator. This molecule breaks the
The principal organic compound that is formed when
(c)
Interpretation:
The principal organic compound that is expected when product(s) of part (b) undergo solvolysis in aqueous acetone is to be stated.
Concept introduction:
The nucleophilic substitution reactions are the reactions in which a group is substituted by a nucleophile. The
The
Answer to Problem 17.22AP
The principal organic compounds that are formed when product(s) of part (b) undergo solvolysis in aqueous acetone are shown below.
Explanation of Solution
The products of part (b) are shown below.
Figure 3
The reaction when product(s) of part (b) undergo solvolysis in aqueous acetone is shown below.
Figure 4
The nucleophilic substitution reaction takes place when solvolysis of products of part (b) takes place. The bromine group is substituted by the hydroxyl group giving rise to the formation of an allylic alcohol.
The principal organic compound that is formed when product(s) of part (b) undergo solvolysis in aqueous acetone is shown in Figure 4.
(d)
Interpretation:
The principal organic compound that is expected when product(s) of part (b) are reacted with
Concept introduction:
The reaction of an
Answer to Problem 17.22AP
The principal organic compounds that are formed when product(s) of part (b) are reacted with
Explanation of Solution
The products of part (b) are shown below.
Figure 3
The reaction that occurs when product(s) of part (b) are reacted with
Figure 5
The allylic halide also undergoes the same kind of reactions are do the alkyl halide with magnesium metal in dry ether. They are also lead to the formation of Grignard reagent but this time with the allylic group.
The principal organic compound that is formed when product(s) of part (b) undergo solvolysis in aqueous acetone is shown in Figure 5.
(e)
Interpretation:
The principal organic compound that is expected when product(s) of part (d) are reacted with
Concept introduction:
The reaction of an alkyl halide with a metal-like magnesium in the presence of dry ether leads to the formation of
Answer to Problem 17.22AP
The principal organic compound that is formed when products of part (d) react with
Explanation of Solution
The products of part (d) are shown below.
Figure 6
The Gringnard reagents react with
Figure 7
The principal organic compound that is formed when products of part (d) react with
Want to see more full solutions like this?
Chapter 17 Solutions
EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
- Consider the following structural formulas. OH H;C CH3 CH3 F G H (a) Which of the compounds F-l can easily be subjected to an elimination reaction? (b) Provide the reaction mechanism for all eliminations under (a).arrow_forwardPredict the major product or the necessary reagent or reactant to complete each of the following reactions. In the box before each reaction, indicate the mechanism followed by the reaction. (Free radical (FR), SN2, SN1). (b) (a) Cl₂ CH₂CH₂OH (a) 1 hv 2 (b) H Br H₂O Na+ SCH3 (c) (d) CI "CH3arrow_forwardhow to slove this question?arrow_forward
- (a) Draw the mechanism for the formation of both of the enols that can be formed from A (use acetic acid & AcOH as the source of the protons) (b) Draw the mechanism of reaction of this enol with bromine to give product Barrow_forwardProvide reagentsarrow_forward(3) (a) Predict the product of the reaction between benzoyl chloride and any one of the following reagents. (i) Li(Et),Cu in ether (ii) BuMgBr in ether, then H3O+arrow_forward
- (i) Name, draw and describe the organic product of the reaction between 2-methylbut-1-ene and H2O in the presence of H2SO4 and provide a clear rationale as to why this is the major product of the reaction. (ii) The elimination reaction between 2-bromobutane and NaOCH2CH3 gives two organic products. Draw a mechanism for the reaction which produces the major organic elimination product and provide a rationale as to why that is the major product.arrow_forwardSyntheses of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short sequences of reactions that would be appropriate for each transformation. (a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanonearrow_forwardc) An alkyl halide E, C5H11B1 undergoes hydrolysis to form an alcohol F, C5H120. Alcohol F becomes cloudy immediately when reacted with a Lucas reagent. (i) (ii) Deduce the structures of E and F. State the type of reaction and propose the mechanism for the conversion of E to F. d) Draw the structure of the product formed when 2-bromopropane reacts with the following reagents respectively, (i) (ii) potassium cyanide ethoxide ionarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY