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Exam 4 Study Guide

by: Hayley Lecker

Exam 4 Study Guide CHEM 2325 - 001

Hayley Lecker
GPA 3.42

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This covers Carbohydrates: reactions, D and L, R and S, Beta and Alpha Amino Acids Synthetic Polymers
Organic Chemistry - 12551
James Salvador
Study Guide
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This 21 page Study Guide was uploaded by Hayley Lecker on Tuesday May 10, 2016. The Study Guide belongs to CHEM 2325 - 001 at University of Texas at El Paso taught by James Salvador in Fall 2015. Since its upload, it has received 67 views.


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Date Created: 05/10/16
OrganicChemistry 2Exam4Study Guide D vs. L, R vs. S Important thing to know Is that a D chiral center will be R and a L chiral center will be S: EXCEPTION Cysteine. So to figure out if it is D or L you take the LAST CHIRAL CENTER from the top then you determine R or S. D vs. L in ring, Beta vs. Alpha Now determining D or L in cyclic form may be a little tricky so I am going to include a tutorial that was VERY useful to me credit to ULCA: The first part covers converting ACYCLIC TO cyclic, since that is something important to know. The second part covers converting CYCLIC back to acyclic . The third part covers D or L in a ring. The final part covers alpha and beta. I know alpha and beta has been a little confusing through the semester. Part 1 on the next page: Part 1 continued on the next page: Part 2: Part 2 continued next page: Part 2 continued next page Part 2 continued on next page Part 3: Start on Next page sorry Part 4: Amino Acids - Now that we know the essentials of carbohydrates (I will talk about the reactions later) let’s move onto the essentials of amino acids and dipeptides. A quick note about this guide they show all the amino acids as NH2 and OH groups for this lesson take the hydrogen off of the OH group of the carboxylic group and give it to the NH2 group. Also all the amino acids above are in L or S form except Cysteine which is R in L form. We as humans live in the L form of the amino acids, bacteria live in D form. Glycine is the only non-chiral amino acid. Isoleucine is erythro meaning both of its chiral centers have groups on the same side: See the NH2 and CH3 are on the same side. Dipeptide time, I am going to include something I drew up for week 14 lesson: Starts on Next page cause these are full pages. Essential R 3 letters isoleucine (S)-sec-butyl Ile leucine isobutyl Leu lysine 4-aminobutyl Lys methionine 2-(methylsulfanyl)ethyl Met phenylalanine benzyl Phe threonine (R)-1-hydroxyethyl Thr tryptophan 3-indolylmethyl Trp valine isopropyl Val ‘ Above is the table with the names and three letters if you don’t already know the names associated with them. Synthetic Polymers If all of the phenyl groups are on the same side of the chain, we say the polymer is isotactic. If the phenyl groups come on alternating sides of the chain, the polymer is said to be syndiotactic. If the phenyl groups are on both sides and right and left follow in no particular order, in a random fashion, than we say the polymer is atactic. Using polystyrene as the example here. Monomers- I am going to try to cover as many as I can: Monomer of Plexiglass- methyl methacrylate Monomer of Plastic Bottlecaps: propene Monomer of Teflon coating: tetrafluoroethylene Monomer of credit cards – chloroethene Monomer of white glue: vinyl acetate Monomer of milk jugs: ethene Monomer of toothbrush bristles: Caprolactam Monomer of rubber: isoprene Monomer of plastic disposable coffee cups: styrene Monomers of nylon: Monomer of “new car smell”: instead of “Ethyl” its methylhexyl Initiators start the process for polymers to form from monomers. Plasticizers help things dissolve. A few initiators: AIBN: ABCN: Dicumyl peroxide: Dibutyl peroxide: Potassium persulfate: REACTION TIME!! The most common carbohydrate is glucose, which is a monsaccharide, an aldohexanose and a reducing sugar. Below is an image showing the different reactions with glucose: First reaction: Oxidation. If a sugar can be oxidized is it is a reducing sugar. Here is an example of an oxidation note the end with the OH is being reduced. Note: achiral means optically inactive, chiral means optically active. Reduction: Sodium borohydride reduction of an aldose makes the ends of the resulting alditol chain identical, HOCH (2HOH) CH nH,2thereby accomplishing the same configurational change produced by oxidation to an aldaric acid. Thus, allitol and galactitol from reduction of allose and galactose are achiral, and altrose and talose are reduced to the same chiral alditol. A summary of these redox reactions, and derivative nomenclature is given in the following table. Derivatives of HOCH (2HOH) CHn HOBr Oxidation ——> HOCH (2HOH) CO n 2 an Aldonic Acid HNO O3idation ——> H 2C(CHOH) COnH 2 an Aldaric Acid NaBH R4duction ——> HOCH (2HOH) CH nH 2 an Alditol Chain Shortening and Lengthing: Summary of reactions: Synthesis of a carbohydrate from a smaller carbohydrate is a Fischer reactions. Synthesis of a carbohydrate from a large carbohydrate is a Ruff degradation. Now on to amino acid reactions: Synthesis to isolate an alpha-amino acid derivate from a polypeptide is Edman degradation. Synthesis of an alpha-amino acid from an aldehyde is a Strecker synthesis: Synthesis of an alpha-amino acid from an carboxylic acid is Aminatation of alpha-bromocarboxylic acids:


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