22.64 22.64 Which compound in each of the sets shown in Fig. P22.64(b) As the above data show, the AG° for hydrolysis of Aof bromine, bromoacetone is isolatecCH3The rate of appearance of bromoacerthe following rate law:rate = k[acetoacetic aci-AG° (hydrolysis) =-67.3 kJ mol-1AG° (hydrolysis) =-30.9 kJ mol-1(The reaction rate is zero order in brcmechanism for the reaction that is cois much more negative than the AG° for hydrolysis ofphenyl acetate (B). Explain why the equilibrium for thehydrolysis of A is much more favorable than the equi-librium for the hydrolysis of B.law.22.69 Account for the fact that treatment of1,3-propanedione with I, and NaOH gtate of iodoform even though it is notBesides iodoform, the other product oacidification, is two equivalents of beris most acidic? Explain.2.65 Arrange the following compounds in order of increasingacidity and explain.(1) isobutyramideCH(2) octanoic acid1,3-diphenyl-1,3-propanedi(3) toluene(4) ethyl acetate(5) phenylacetylene(6) phenol(a)CH,CCH,CCH3,CH,CCH,CCH,PhCH3CCHCCH3,orPh(b)C-CH3CH,CH,CH,C-CH3orH2C=CHCH;Figure P22.64H;C-C-CH;-Br + HBr + CO,Н,С—С—СH, —С—ОН + Brzbromoacetoneacetoacetic acidFigure P22.68

Answered: Image /qna-images/answer/95f3dfbd-2d33-4411-9ad8-fdb9dca2a432.jpg

22.64 Which compound in each of the sets shown in Fig. P22.64 is most acidic? Explain. Besides iodoform, the c acidification, is two equ 2 65 Arrange the following compounds in order of increasing acidity and explain. (1) isobutyramide (2) octanoic acid 1,3-diphenyl- (3) toluene (4) ethyl acetate (5) phenylacetylene (6) phenol (a) CH,CCH,CCH3, CH,CCHCCH3, CH,CCH,CCH,Ph or Ph (b) or CH;CH,CH,-C-CH3 H,C=CHCH,-C-CH3 Figure P22.64

22.64 Which compound in each of the sets shown in Fig. P22.64 is most acidic? Explain. Besides iodoform, the c acidification, is two equ 2 65 Arrange the following compounds in order of increasing acidity and explain. (1) isobutyramide (2) octanoic acid 1,3-diphenyl- (3) toluene (4) ethyl acetate (5) phenylacetylene (6) phenol (a) CH,CCH,CCH3, CH,CCHCCH3, CH,CCH,CCH,Ph or Ph (b) or CH;CH,CH,-C-CH3 H,C=CHCH,-C-CH3 Figure P22.64

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.58P

See similar textbooks

Similar questions

22:43 10. Provide the following: the resonance structure of the intermediate that can resonate into the other intermediate that is given the product that results from the given resonance structure Specify which product is the kinetic product and which is the thermodynamic product . OH 50% H₂SO4 H~
(a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?
Are the following halogenated or non- halogented?(a) Cyclohexyl hydrogen sulfate(b) p-Toluenesulfonic acid
Quinapril (trade name Accupril) is used to treat high blood pressure andcongestive heart failure. One step in the synthesis of quinapril involvesreaction of the racemic alkyl bromide A with a single enantiomer of theamino ester B. Given the structure of quinapril, which one of these two products isneeded to synthesize the drug?
3) Draw equations of the following reactions and and explain to which direction is the respective quillibrium shifted. a) cyclohexylamine + water b) aniline + sulphuric acid c) triethylamine + acetic acid
Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
21.41 Identify a systematic (IUPAC) name for each of the following compounds: (a) OH (b) NH2 (c) CI
Question: Which of the following is the major product from bromination of meta-nitrobenzenesulfonic acid? * Br Br2 , FeBra heat NO2 or or or NO2 NO2 NO2 NO2 B. D. (A) (B) Question: C6H5OCH2CH2Br is heated with Mg in ether and then quenched in cold H2O. What organic product will be obtained ? * C6H50CH2CH3 C6H50CH2CH2OH C6H50H C6H6
Provide the major organic products(s) of the reaction shown:.
(b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid coniine (isolated from hemlock), starting from octanoic acid. Coniine
Write the structures of the following compounds:(a) Butyldiethylammonium bromide (b) Tetrabutylammonium hydroxide(c) Propylammonium iodide (d) Isopropylmethylammonium chloride
Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?