Solution the art of writing reasonable organic reaction mechanisms

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Solution the art of writing reasonable organic reaction mechanisms

Answers To Chapter 1 In-Chapter Problems.1.1. The resonance structure on the right is better because every atom has its octet."C=o+H?(;+H3C+N=CH, **N—

Solution the art of writing reasonable organic reaction mechanisms —CH,h3ch3cthe second structure is hopelessly strainedChapter ỉ1.4. The o atom in furan has sp2 hybridization. One lone pair resides in the p orbital a

nd is used in resonance; the other resides in an sp2 orbital and is not used in resonance.1.5.(a) No by-products. C( 1-3) and C(6-9) are the keys to n Solution the art of writing reasonable organic reaction mechanisms

umbering.(b) After numbering the major product. C6 and Br25 are left over, so make a bond between them and call it the by-product.5 OMe62425Br—Br1.6.(

Solution the art of writing reasonable organic reaction mechanisms

a) Make C4-O12, C6-C11, C9-O12. Break C4-C6. C9-CH, Cl 1-012.(b) Make C8-N10. C9-C13. C12-Br24. Break O5-C6. C8-C9.1.7.PhC=CH is much more acidic than

Answers To Chapter 1 In-Chapter Problems.1.1. The resonance structure on the right is better because every atom has its octet."C=o+H?(;+H3C+N=CH, **N—

Solution the art of writing reasonable organic reaction mechanisms pẢ’a « 17) than the c a 10 the ketone (pÂ3 ss 20). Because the by-product of the reaction is HiO. there is no need to break the o H bond to get to pro

duct, but the C-H bond a to the ketone mast be broken.Chapter ỉAnswers To Chapter 1 End-Of-Chapter Problems.1. (a) Both N and o in amides have lone pa Solution the art of writing reasonable organic reaction mechanisms

irs that can react with electrophiles. When the o reacts with an electrophile E+. a product is obtained for which two good resonance structures can be

Solution the art of writing reasonable organic reaction mechanisms

drawn. When the N reacts, only one good resonance structure can be drawn for the product.reaction on oreaction on NE R(b) Esters are lower in energy

Answers To Chapter 1 In-Chapter Problems.1.1. The resonance structure on the right is better because every atom has its octet."C=o+H?(;+H3C+N=CH, **N—

Solution the art of writing reasonable organic reaction mechanisms iate is obtained for which resonance is not nearly as important, and therefore the tetrahedral product from the ester is nearly the same energy as the

tetrahedral product from the ketone. As a result it costs more energy to add a nucleophile to an ester than it does to add one to a ketone.(c) Exactl Solution the art of writing reasonable organic reaction mechanisms

y the same argument as in (b) can be applied to the acidity of acyl chlorides versus the acidity of esters. Note that Cl and o have the same electrone

Solution the art of writing reasonable organic reaction mechanisms

gativity, so the difference in acidity between acyl chlorides and esters cannot be due to inductive effects and must be due to resonance effects. A

Answers To Chapter 1 In-Chapter Problems.1.1. The resonance structure on the right is better because every atom has its octet."C=o+H?(;+H3C+N=CH, **N—

Solution the art of writing reasonable organic reaction mechanisms case the two rings are made aromatic, so it is much more important than normal.(e)The difference between 3 and 4 is that the former is cyclic. Loss of

an acidic H from the y c of 3 gives a structure for which an aromatic resonance structure can be drawn. This is not true of 4.(f)Both imidazole and p Solution the art of writing reasonable organic reaction mechanisms

yridine are aromatic compounds. The lone paữ of the H-bearing N in imidazole is required to maintain aromaticity, so the other N, which has its lone p

Solution the art of writing reasonable organic reaction mechanisms

air in an sp2 orbital that is perpendicular to the aromatic system, is the basic one. Protonation of this N gives a compound for which twoChapter 15

Answers To Chapter 1 In-Chapter Problems.1.1. The resonance structure on the right is better because every atom has its octet."C=o+H?(;+H3C+N=CH, **N—