Suggested solution the functional groups shouldnt have

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Unformatted text preview: rketed by Roche Purpose of the problem To persuade you that functional groups are easy to identify even in complicated structures: an ester is an ester no matter what company it keeps and it can be helpful to look at the nature of the carbon framework too. Suggested solution The functional groups shouldn’t have given you any problem except perhaps for the sulfide (or thioether) and the phenol (or alcohol). You should have seen that both molecules have an amide as well as an amine. 3 Solutions for Chapter 2 – Organic Structures HO O ester ether amine NH2 HH N H sulfide O N H3C O amide amide phenol or alcohol O H3C S CO2H CH3 HN H3C carboxylic acid O O NH2 amine amide The ring sizes are easy and we hope you noticed that the black bond between the four- and the five- membered ring in the penicillin is shared by both rings. six-membered NH2 O HO O five- H membered H3C S HH N N O H3C O CO2H four-membered O HN H 3C CH3 six-membered O NH2 The carbon chains are quite varied in length and style and are broken up by N, O, and S atoms. cyclic C6 HO NH2 cyclic C3 HH N O linear C2 branched C5 CO2H H3C linear C2 O CH3 cyclic C6 HN linear C2 H3C O H3C S N O O linear C5 H O NH2 4 Solutions Manual to accompany Organic Chemistry 2e PROBLEM 3 What is wrong with these structures? Suggest better ways to represent these molecules H C C H H O H H 2C NH OH H N H 2C Me H H H CH2 NH2 CH2 Purpose of the problem To shock you with two dreadful structures and to try to convince you that well drawn realistic structures are more attractive to the eye as well as easier to understand and quicker to draw. Suggested solution The bond angles are grotesque...
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