Clayden Organic Chemistry Solutions Manual 2nd Edition
2 Suggested solutions for Chapter 2 PROBLEM 1 Draw good diagrams of saturated hydrocarbons with seven carbon atoms having (a) linear, (b) branched, and (c) cyclic structures. Draw molecules based on each framework having both ketone and carboxylic acid functional groups in the same molecule. Purpose of the problem To get you drawing simple structures realistically and to steer you away from rules and names towards more creative ideas. Suggested solution There is only one linear hydrocarbon but there are many branched and cyclic options. We offer some possibilities, but you may have thought of others.
- Organic Chemistry Clayden Solutions Manual Organic Chemistry Clayden Solutions. Paperback, 1508 Pages First Edition, 20 Juli 2000 ISBN: 0-198-50346-6 Oxford University Press DOWNLOAD. Description A first and second year undergraduate organic chemistry textbook, specifically geared to British and European courses and courses offered in better.
- Oxford University Press, 2nd edition, 2013, 520p., ISBN 978 0 19 966334 7 This is an additional resource to the popular textbook of Organic Chemistry 2nd.
Linear saturated hydrocarbon (n-heptane) some branched hydrocarbons some cyclic hydrocarbons We give you a few examples of keto-‐carboxylic acids based on these structures. A ketone has to have a carbonyl group not at the end of a chain; a carboxylic acid functional group by contrast has to be at the end of a chain. You will notice that no carboxylic acid based on the first three cyclic structures is possible without adding another carbon atom. 2 Solutions Manual to accompany Organic Chemistry 2e O linear molecules containing ketone and carboxylic acid CO2H CO2H O some branched keto-acids CO2H O CO2H HO2C HO2C O O O some cyclic keto-acids O O CO2H CO2H HO2C CO2H O O PROBLEM 2 Draw for yourself the structures of amoxicillin and Tamiflu on page 10 of the textbook. Identify on your diagrams the functional groups present in each molecule and the ring sizes. Study the carbon framework: is there a single carbon chain or more than one? Are they linear, branched, or cyclic?
NH2 H H N O H S O H3C HO O O CH3 N O H3C HN CO2H SmithKline Beechamʼs amoxycillin β-lactam antibiotic for treatment of bacterial infections H3C O NH2 Tamiflu (oseltamivir) invented by Gilead Sciences marketed 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 H H 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 H H 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.
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Cyclic C6 HO NH2 cyclic C3 H H 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 H O C C H 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 with square planar saturated carbon atoms, bent alkynes with 120° bonds, linear alkenes with bonds at 90° or 180°, bonds coming off a benzene ring at the wrong angles and so on. If properly drawn, the left hand structure will be clearer without the hydrogen atoms. Here are better structures for each compound but you can think of many other possibilities. O N OH N H NH2 PROBLEM 4 Draw structures for the compounds named systematically here.
In each case suggest alternative names that might convey the structure more clearly if you were speaking to someone rather than writing. (a) 1,4-‐di-‐(1,1-‐dimethylethyl)benzene (b) 1-‐(prop-‐2-‐enyloxy)prop-‐2-‐ene (c) cyclohexa-‐1,3,5-‐triene Purpose of the problem To help you appreciate the limitations of systematic names, the usefulness of part structures and, in the case of (c), to amuse.
Solutions for Chapter 2 – Organic Structures Suggested solution (a) A more helpful name would be para-‐di-‐t-‐butyl benzene. It is sold as 1,4-‐di-‐tert-‐butyl benzene, an equally helpful name.
There are two separate numerical relationships. 4 the 1,1-dimethyl ethyl group 1 1 2 3 2 1,4-relationship between the two substituents on the benzene ring (b) This name fails to convey neither the simple symmetrical structure nor the fact that it contains two allyl groups. Most chemists would call it ‘diallyl ether’ though it is sold as ‘allyl ether’.
The allyl group O the allyl group (c) This is of course simply benzene! PROBLEM 5 Translate these very poor structural descriptions into something more realistic. Try to get the angles about right and, whatever you do, don’t include any square planar carbon atoms or any other bond angles of 90°. (a) C6H5CH(OH)(CH2)4COC2H5 (b) O(CH2CH2)2O (c) (CH3O)2CH=CHCH(OMe)2 Purpose of the problem An exercise in interpretation and composition. This sort of ‘structure’ is sometimes used in printed text.
Clayden Organic Chemistry Solutions Manual
It gives no clue to the shape of the molecule. Suggested solution You probably needed a few ‘trial and error’ drawings first but simply drawing out the carbon chain gives you a good start. The first is straightforward—the (OH) group is a substituent joined to the chain and not part of it. The second compound must be cyclic—it is the ether solvent commonly known as dioxane.
The third gives no hint as to the shape of the alkene and we have chosen trans. It also has two ways of 5 6 Solutions Manual to accompany Organic Chemistry 2e representing a methyl group. Either is fine, but it is better not to mix the two in one structure. C6H5CH(OH).(CH2)4COC2H5 O(CH2CH2)2O OH (CH3O)2CH=CHCH(OMe)2 OMe O O O OMe MeO OMe PROBLEM 6 Suggest at least six different structures that would fit the formula C4H7NO. Make good realistic diagrams of each one and say which functional groups are present. Purpose of the problem The identification and naming of functional groups is more important than the naming of compounds, because the names of functional groups tell you about their chemistry.
This was your chance to experiment with different groups and different carbon skeletons and to experience the large number of compounds you could make from a formula with few atoms. Suggested solution We give twelve possible structures – there are of course many more. You need not have used the names in brackets as they are ones more experience chemists might use.
Organic chemistry clayden 2nd edition solutions manual pdf. 1. ORGANIC CHEMISTRY CLAYDEN 2ND EDITION SOLUTIONS MANUAL PDF - PDF 96 Pages 500.16 KB 21 May, 2016 - COPYRIGHT 2015, ALL RIGHT RESERVED Save this Book to Read organic chemistry clayden 2nd edition solutions manual pdf PDF eBook at our Online Library. Get organic chemistry clayden 2nd edition solutions manual pdf PDF file for free fr PDF file: organic chemistry clayden 2nd edition solutions manual pdf Page: 1. ORGANIC CHEMISTRY CLAYDEN 2ND EDITION SOLUTIONS MANUAL PDF This eBook discuss about the subject of ORGANIC CHEMISTRY CLAYDEN 2ND EDITION SOLUTIONS MANUAL PDF, along with the whole set of accommodating tips plus details about that subject. You could read the content material sneak peek through the table of content under (in case available), that's start from the Introduction, Brief Description till the Glossary page.
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