Interpretation:
The detailed mechanism for the given reaction is to be proposed.
Concept introduction:
Reaction mechanism is the step by step sequence of elementary reactions.
Reaction sequences involve conversion of one functional group to another, which may also require addition or loss of carbon from the reactant.
These sequences involve a number of steps carried out by different reagents. Sometimes different reagents give the same products.
Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Nucleophilic substitution reaction is a reaction in which an electron-rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
An
An
The involvement of nearby nucleophile substituent to the reaction center in the substitution process is known as neighboring group participation.
Such participation results in an increase of
In this participation, two
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Chapter 6 Solutions
Organic Chemistry
- The acid-catalyzed hydrolysis of an ester converts an ester into a carboxylic acid. Although there are two O atoms that can be protonated, the first step in the mechanism is believed to be protonation of the oxygen in the C=0 group. Based on charge stability, why is it favorable to protonate that oxygen? Hint: Draw out the products of each protonation. + Hо HO, НО Carboxylic acid Ester Alcoholarrow_forward7.) Which of the following is the product of CH,CHO + [Ag(NH3)2J* + OH- – product + Ag + H,0 + NH3 (1) CH,COO- (2) CH,CH,O (3) CH,COOA9 (4) CH;O-arrow_forwardCH,- CH = 0 aldehyde CH, О— С — С — Н CH3 NH,–C=O | - CH3 CH, CH, — CH, —С — ОНarrow_forward
- Below are isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert- butylcyclohexanol and two are cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation for each pair, and indicate which of all four conformations is the most stable. A OH Ex HO B D OH OHarrow_forwardShown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. • Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P. • Double click to select atoms. • You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).arrow_forwardN,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below draw the structure of the product of this reaction. MgBr H3C 0 ▾ + 1. CO₂ 2. H3O+ • 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. • Draw the Grignard reagent as a covalent magnesium bromide. n [ ]# product ChemDoodleⓇ 28arrow_forward
- An alkene forms 2-methylbutane when catalytically reduced and 2,3- dibromo-2-methylbutane when treated with Br₂. Draw the structural formula of the alkene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. . In cases where there is more than one answer, just draw one. / 8 MULL / #[ ] در O- √n ?arrow_forwardThere are three different dichloroethylenes (molecular for-mula C₂H₂Cl₂), which we can designate X, Y, and Z. CompoundX has no dipole moment, but compound Z does. Compounds Xand Z each combine with hydrogen to give the same product:C₂H₂Cl₂ (X or Z) +H₂→ClCH2-CH2Cl What are the structures of X, Y, and Z? Would you expect com-pound Y to have a dipole momenarrow_forward• -- H (b) H,C 3-methylhexane CH, (c) B கூ CH, CH, HgCG; சீகூ H₂CH H 3-ethyl-1-methyloctane 3,3 diethyl pentane 5Å, Å,CH, W CH3 CH2 CH₂ W21 Su2... CH3 X -CH3 G b F E L carrow_forward
- compound family I| CH, — С — он carboxylic acid | CH, CH;- CH, C- OH CH, 0=C-C- H NH, CH,- NH - CH3arrow_forwardIntramolecular H-bonding (IHB) are interactions that occur within one single molecule. IHB is also known as chelation, since it involves ring formation. Which of the following is (are) stabilized by IHB? a b c darrow_forwardsketch the various conformational isomers of 1,3-dimethylcyclohexane. Indicate the position (axial/equatorial) of each of the methyl groups in each structure.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning