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I 14.10 Draw a structural formula for each carboxylic acid: (SeeJ Example 14.1) { 'l (a) 4-Nitrophenylacetic acid ;:' (b) 4-Aminopentanoic acid ( c) 3-Chloro-4-phenylbutanoic acid ( d) cis-3-Hexenedioic acid ( e) 2,3-Dihydroxypropanoic acid (f) 3-0xohexanoic acid (g) Z-Oxocyclohexanecarboxylic acid (h) z,2-Dimethylpropanoic acid • 1 1--1, Section 14.4 Preparation of Carboxylic Acids 14_18 Ora~ a structural formula f~r the product formed by treating each compound with warm chromic acid, H2Cr04: (a) CH3(CH2)4CH20H (b) Acidity of Carboxylic Acids 14.20 Which is the stronger acid in each pair? (See Example 14.2) (a) Phenol (pKa 9.95) or benzoic acid (pKa 4.17) (b) Lactic acid (Ka 1.4 X 10-4) or ascorbic acid (Ka 6.8 X 10-5) I -- . ~o'( ,7 Tt•sl your cumulallv~ knowledge o~ the reactions learned 0) ~ 1"- thus far by completing the following chemical transfornrntions. Note: Some will require more than one step. OH (See Examples 14.4-14.7) a),OH ylo~ (j) C>= C>-{ aOH 0oto do~ (k) ~ (b) -0 0 0---{_/ (c) ~OH ~0/ (I) 0-CI (d) Na•o-1y y (m)~ 0 ~ 0 (e) 0-oH--+ o-~-o 0 (n) y ~o~ Br ( 0 ~ Cl~ (o) H3C--0==C-H 0 JOH (g) 0 Cl 0 doCH, -0 (p) 0 0 o,Ndcr I "° 0 (h)~OH 6 Section 15.1 Structure and Nomenclature 15.9 Draw a structural formula for each compound: (See Example 15.1) (a) Dimethyl carbonate (b) p-Nitrobenzamide (c) Octanoyl chloride ( d) Diethyl oxalate (e) Ethyl cis-2-pentenoate (f) Butanoic anhydride (g) Dodecanamide (h) Ethyl 3-hydrm.,'Ybutanoate (i) Ethyl benzoate (j) Benzoyl chloride 15.10 Write the IUJ>AC name for each compound: (See Exam11le 1.5.1) (a) o\\ aII - -~\ ...:::===..J >--C-0·-C -v 0 (b) CH3(CH2)iJOCH3 15.19 Balance and write a mechanism for each of the following reactions. (See Examples 15.2, 15.4, 15.5) (a) 0 (b) '-... ~ 0 0 0 (c) )lo~ 0 0 + NH4C1 CJ 0 HO~ + CH3OH I I I I I 15.31 Show the product of treating -y-butyrolactone with eacn reagent: (See Examples 15.2, 15.S, 15.7) (a) NH3 (b) LiAIH4/ether, then H2O (c) NaOH, H2O, heat 16.13 Identify the most acidic hydrogen(s) in each compound: (See Example 16.1) 0 0 (a) H (b) H3CO 0 (c) (d) HO 0 0 0 i ' \ (e) l ~ HO ~ (f) OH 16.18 Draw a structural formula for the product of each crossed aldol reaction and for the compound formed b dehydration of each aldol product: (See Examples 161, 16.4) 0 0 H (b) + CHO (c) + CHO 0 (d) 16.27 Show the product of the Claisen condensation of each ester: (See Example 16.6) (a) 0 NaOEt 0 (b) NaOCH3 > 0 (c) NaOEt Section 18.2 Monosaccharides 18.8 What is the difference in structure between an aldose and -- a ketose? Between an aldopentose and a ketopentose? 18. 9 Which hexose is also known as dextrose? 18.10 What does it mean to say that o- and L-glyceraldehyde are enantiomers? 18.11 Explain the meaning of the designations o and L as used - to specify the configuration of carbohydrates. 18.12 How many stereocenters are present in o-glucose? In -- o-ribose? How many stereoisomers are possible for each monosaccharide? 18.13 Which compounds are o-monosaccharides and which are L-monosaccharides? (See Example 18.1) 19.23 Draw a structural formula for the form of each amino acid most prevalent at pH 10.0 (See Example 19.2): (a) Leucine (b) Valine ( c) Proline ( d) Aspartic acid 19.28 Draw a structural formula for the product formed when alanine is treated with each of the following reagents: (a) Aqueous NaOH (b) Aqueous HCl (c) CH3CH20H, H2S04 (d) (CH3C0)20,CH3COO- Na+ CH 14: 14.10 14.18 14.20 14.47 (include synthetic and/or mechanistic details) 2 Paragraphs: Review section 14.4. Draw the equilibrium for the reaction of water with HF. Describe how you would calculate the Ka. What would a small value of Ka mean? A large value? Knowing that HF is a VERY strong acid, what should the value for Ka be? CH 15: 15.9 15.10 a-d 15.19 15.31 (with mechanisms) CH 16: 16.13 16.18 (with mechanisms) 16.27 2 Paragraphs: Describe why a Michael Reaction works. What is the driving force behind it? In other words: why don’t the reagents just sit there in the flask and do nothing when mixed? 2 Paragraphs: Draw out the complete aldol mechanism. Feature each step and explain why it works – as if you were teaching a class. You may wish to create a PowerPoint presentation for this, or simply have a very detailed writeup. Creativity is encouraged. CH 17: Essay: Describe to your first graders class, what a polymer is and how they form. What is it about them which makes them stronger than many other materials, for example, their monomers? Essay: Go back to Chapter 16. Describe how you might envision a set of monomers which were set up to polymerize based on the following reactions. Be sure to draw out the structural features of the monomers – they don’t have to be real molecules. a) Michael Reaction b) Aldol condensation Essay: There has been a lot in the news over the past years about PET. Describe what the fuss is about? CH 18: Essay: Describe what a monosaccharide is. What is it, structurally, that makes them special to living creatures? 18.8 18.11 (in detail) 18.12 2 Paragraphs: Describe what a lipid is, from the chemical standpoint. What is it, structurally, that allows it to do what it does – and why? I’m asking for structural and electronic details. 2 Paragraphs: Structurally, what is it about synthetic detergents that allow them to work? 2 Paragraphs: Describe the difference between HDL and LDL, from a chemical standpoint. 2 Paragraphs: Describe the Citric acid cycle: what is it and why does it work? When we talk about biological oxidations, what is actually happening as the molecule gets processed? 2 Paragraphs: Describe glycolysis from a chemical standpoint. CH 19: 19.23 19.28 Essay: What is the key bond in any amino acid – and why? Essay: Draw any 3 amino acids and describe which are the Hydrogen bond donor sites and which are hydrogen bond accepter sites? CH 20: Essay: Describe the structure of DNA from a chemical standpoint. What are the different features which components need to have in order to assemble in this way? Essay: How is RNA different from DNA, in structure and function? Essay: Describe how the genetic code is stored in molecules??

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