TUTORIALS ON MECHANISMS NUCLEOPHILIC SUBSTITUTIONS Exercice 1 Determine for each of the following molecules the factors favorable to one or the other type of nucleophilic substitution. Justify H₂CO oto Br .CH₂CI O₂N CH₂CH₂Br CH₂CI CH₂CH3 HC OH Ph Exercice 2 When 2-bromo-2-methylpropane is dissolved in aqueous ethanol at 25 ° C, a mixture of products is obtained. For each of the products, explain their mechanism of formation. Exercice 3 This alcohol, in R configuration, is treated by an aqueous solution of HCl. An inactive mixture of compounds of molecular formula C9H₁1Cl is obtained. Write the mechanism of the reaction CH₂Br COOEt H₂C=CH-CH₂Br Exercice 4 1) Hydrolysis of (1R, 2R) 1-bromo-1,2-dimethylcyclopentane gives alcohols. Specify the stereochemistry of these alcohols. Are they optically active separately? Is their mixture globally active? COOEt 2) If we study the same reaction with (1R, 2R) 1-bromo-2-dimethylcyclopentane, what products would be obtained? Exercice 5 What is the product of the reaction below? justify your answer by writing the mechanism EtONa

TUTORIALS ON MECHANISMS NUCLEOPHILIC SUBSTITUTIONS Exercice 1 Determine for each of the following molecules the factors favorable to one or the other type of nucleophilic substitution. Justify H₂CO oto Br .CH₂CI O₂N CH₂CH₂Br CH₂CI CH₂CH3 HC OH Ph Exercice 2 When 2-bromo-2-methylpropane is dissolved in aqueous ethanol at 25 ° C, a mixture of products is obtained. For each of the products, explain their mechanism of formation. Exercice 3 This alcohol, in R configuration, is treated by an aqueous solution of HCl. An inactive mixture of compounds of molecular formula C9H₁1Cl is obtained. Write the mechanism of the reaction CH₂Br COOEt H₂C=CH-CH₂Br Exercice 4 1) Hydrolysis of (1R, 2R) 1-bromo-1,2-dimethylcyclopentane gives alcohols. Specify the stereochemistry of these alcohols. Are they optically active separately? Is their mixture globally active? COOEt 2) If we study the same reaction with (1R, 2R) 1-bromo-2-dimethylcyclopentane, what products would be obtained? Exercice 5 What is the product of the reaction below? justify your answer by writing the mechanism EtONa

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

See similar textbooks

Similar questions

b) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OH
For following substituted benzenes: [1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3: Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?
Rank the following compounds in order of increasing reactivity in a substitution reaction with −CN as nucleophile.
Which of the following structures and IUPAC names are incorrectly matched? * oe (A) Methyleyclohexanoate (В) `NH2 Br 4-Bromo-3-chlorohexanamide 2-Ethoxypentane (D) HOOC HOOC 3,5-Nonanedioic acid В A D
Arrange the following compounds in order of increasing reactivity in nucleophilic acyl substitution. Y OA> B>C OB> C > A OC> A > B O C> B> A OB> A >C OA> C > B B
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific.
Denote how many nucleophilic centers are present in the following molecular structure (in case of polar bonds show clearly on the structure the dipoles õ+ and d-). :o: сно
.Which one of the following molecules can react as electrophile in reactions with alkenes? CH3OH NaCI HCI KCN NaCI O HCI O KCN O CH3OH
Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4
Organic Chem - nucleophilic substitution
Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents. cyclohexanol and BF3
Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution. CH3CH2CO2H, (CH3CH2CO)2O, CH3CH2CONHCH3