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CLEMSON / Chemistry / CH 105 / hexaphenylbenzene melting point

hexaphenylbenzene melting point

hexaphenylbenzene melting point

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School: Clemson University
Department: Chemistry
Course: Organic Chemistry
Term: Summer 2015
Tags: Organic Chemistry
Cost: 50
Name: Organic 2030
Description: these notes will help you through the course
Uploaded: 05/11/2017
21 Pages 155 Views 0 Unlocks
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With this in mind, what is your definition of plagiarism?




What is the purpose of recrystallization?




Why is it dangerous to heat a liquid in a distilling apparatus that is closed tightly at every joint and has no vent to the atmosphere?



CH 2270  Andrew Larson Distillation  Post­lab Dino 005 1. Why is it dangerous to heat a liquid in a distilling apparatus that is closed tightly at every joint and has no vent to the atmosphere? It is dangerous to heat the apparWe also discuss several other topics like va business law study guide
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atus when it is tightly sealed because all of the  gases inside the apparatus build more and more pressure as the temperature rises and  eventually the glass apparatus could explode shooting hot glass everywhere. 2. In your distillation of the binary mixture, which fractions contained more of the higher boiling component, the earlier fractions or the later fractions? The earlier fractions contained more of the lower boiling component, the middle  fractions most likely are impure containing some of both components, and the last  fractions contain the most of the high boiling components. 3. Does a pure liquid in a distilling flask vaporize all at once when the boiling point is reached? No it vaporizes gradually as the heat allows the molecules to break intermolecular forces and change states from the liquid to the gas phase.CH 2270 Recrystallization ­ Identification of Unknown  Name:  Andrew Larson                       Pre­lab Section/TA: Dino Sulejmanovic  To be completed before you begin experiment 1. What is the purpose of recrystallization? To take a sample that we know is impure and recrystallize it into a pure crystallized  substance again. 2. Look up the “potential unknown” compounds given, find their melting point ranges and draw the structures below. Write these in your notebook for future reference. Acetanilide 113­115 degrees C Benzoic Acid 121­123 degrees C Cinnamic Acid 132­134 degrees C Salicylic Acid 158­160 degrees CN­Phenylsuccinimide 154­156 degrees C Hexaphenylbenzene > 300 degrees C 3. This experiment is the one for which you will write your one written report this semester. This report must be original work, not plagiarized from another source. With this in mind, what is your definition of plagiarism? (This definition need not be original, you can use any source.) Plagiarism ­ the practice of taking someone else's work or ideas and passing them off as  one's own.CH 2270 Distillation  Pre­lab Andrew Larson Section 005 Dino To be completed before you begin experiment 1. Why is it necessary to add a magnetic stirring bar during the distillation of a  liquid? In order to make sure that bumping due to superheating does not occur, it also  helps the solution cool more quickly after the heat is turned off. 2. Does the vapor pressure of a liquid change with temperature and if so, why? Vapor pressure does increase with increasing temperature because more molecules are  striking the walls of the container and the top with more force. 3. Where do you obtain the glassware needed for distillation in this experiment? The glassware is located in blue bins in the stock room.  4. When attaching the hoses for the cooling water in the distillation apparatus, does the water enter at the top of the condenser and exit at the bottom or enter at the lower end and exit at the upper end? Water enters in the bottom end of the condenser and travels out the top end back into the  sink.CH 2270 Andrew Larson TLC ­ Analysis of Analgesics Name Pre­Lab  Dino 005 1. Draw and label a typical TLC set up. Include developing chamber, watch glass (lid), filter paper, solvent, and TLC plate. Watch Glass Developing  Chamber Filter Paper Solvent TLC Plate2. What is the thin layer in TLC? The thin layer in TLC is whatever substance the adsorbant that is covering the TLC plate  is.  3. Describe how you will measure the Rf of a compound analyzed by TLC? Rf will be calculated by taking the distance the compound has traveled from the  origin and dividing it by the distance the developing solvent has traveled from the origin. CH 2270 Post­lab: Synthesis of n­Butyl Bromide from n­Butanol Andrew Larson Dino 005 1. Draw the structures of n­butyl alcohol and n­butyl bromide. 2. How many moles of n­butyl alcohol did you use in the synthesis of n­butyl bromide? (Show your calculations, not just the answer.) 10 ml x (0.81g/ml) = 8.1 grams / 74.12 g/mol = 0.110 moles n butyl alcohol 3. What is the theoretical yield of n­butyl bromide in grams? (Show your calculations, not just the answer.) .110 moles NBA x (1 mole NBB/ 1 mole NBA) x 137.02g/mole = 15.07 grams 4. What was your percent yield of n­butyl bromide? ? (Show your calculations, not just the answer.) 8.13 grams/15.07 grams = 53.9% yieldCH 2270 Post­lab: Stilbene to Stilbenedibromide Andrew Larson/ Section 005/ Dino 1.How many grams of stilbene dibromide did you isolate? 5.78 grams Stilbene Dibromide 2. What was your percent yield of stilbene dibromide? (Show your calculations, not just the answer.) expected yield = .0222 moles ( 7.546 grams stilbene dibromide) 5.78grams / 7.546 grams = 76.5 % yield 3.What was the melting point of the stilbene dibromide that you isolated? 239 degrees Celcius 4. Which stereoisomer of stilbene dibromide did you synthesize? Meso stilbene dibromide OCHEM STUDY SHEET TEST 1 ANDREW LARSON Formal Charge – (# of valence electrons) - # of bonds - # of electrons  in lone pairs Molecular Charge – sum of all formal charges on a molecule Strong Acids have high Ka and low pKa Comparing for better Anion – Left/Right Electronegativity Up/Down SEHRI Size – larger is better at stabilizing Hybridization – lower hybridization is better at stabilizing (sp is best) Resonance – whenever there is a charge or double bond, near a double bond Inductive Effect – partial charges near a formal charge (can be  stabilizing or destabilizing) C C --- C ---OH Tert – 3 C-C bonds C Iso – In the middle Dashed line means going into the plane Triangle means coming out of the plane Axial is straight up or down 2EQ/2 Axial  1EQ/1Axial Equatorial is slightly up or down 1,2 or 1,4 trans or 1,3 cis 1,2 or 1,4 cis or 1,3 trans Cis is up and up or down and down (Z) Trans is up and down (E) For acids if pH > pKa then they will lose the H+ If pKa > pH then keep H+ For bases pH > pKa of conjugate acid then it won’t get a H+ pKa (conjugate acid) > pH it will get a H+ Constitutional Isomers – same molecular formula/different shapes E/Z priority – 1. Heavier atoms 2. Multiple bonds 3. Size (around double bonds) R vs. S Priority 1. Heavier atoms 2. Multiple bonds 3. Size (Carbon with  4 diff. subs) 2. If lowest priority in back 1-2-3 (R is clockwise, S is counterclockwise) 3. If lowest priority in front 3-2-1 4. If lowest priority is in plane, switch with what is in the back 3-2-1Stereoisomers - are isomeric molecules that have the same  molecular formula and sequence of bonded atoms, but that differ only  in the three-dimensional orientations of their atoms in space. Enantiomers – nonsuperimposable mirror images (have identical  properties) Diastereomers – nonsuperimposable non mirror imagesCH 2230 Fall 2014 Practice Exam #2 ______ 1. Which of the following is the correct protonation state of the amino acid glycine at pH 12: (A) NH3+CH2COOH (B) NH3+CH2COO- (C) NH2CH2COOH (D) NH2CH2COO- ______ 2. Which of the following alkene reactions can have carbocation rearrangements? (A) Hydrogenation (B) Hydroboration/oxidation (C) Halogenation (D) Hydration using water and acid ______ 3. Which of the following alkene reactions proceeds through an anti mechanism? (A) Hydrogenation (B) Hydroboration/oxidation (C) Halogenation (D) Hydration using water and acid ______ 4. Which product will result from the reaction of 1,2-dimethylcyclohexene with BH3 followed by treatment with H2O2 under basic aqueous conditions? A B C D H OH OH OH OH H HH ______ 5. Which of the following structures does NOT have resonance structures? ______ 6. Which of these is the least reasonable product of the reaction of 3-methybutene with water and sulfuric acid? OH A B C D OH OHOH ______ 7. Which of the following molecules is most likely to undergo carbocation rearrangement during its reaction with HBr? A B C D ______ 8. What is the stereochemistry of D-fructose (shown on right, carbon 6 is on bottom)? (A) (3R, 4R, 5S) (B) (3S, 4R, 5R) (C) (3R, 4S, 5S) (D) (3S, 4R, 5S) ______ 9. What’s wrong with this mechanism? (A) Arrow is not following electrons (B) Electrons are moving from a nucleophile to a nucleophile (C) Electrons are moving from an electrophile to an electrophile (D) There is no carbocation rearrangement ______ 10. What’s wrong with this mechanism? (A) Arrow is not following electrons (B) Electrons are moving from a nucleophile to a nucleophile (C) Electrons are moving from an electrophile to an electrophile (D) There is no carbocation rearrangement ______ 11. Which of these molecules would undergo carbocation rearrangement upon reacting with HCl? A B C D ______ 12. How many different products (including steroisomers) will form from the hydrogenation of 2,3-dimethyl-2-pentene? (A) 1 (B) 2 (C) 3 (D) 4 (E) 8 ______ 13. How many different major products (including steroisomers) will form from the reaction of 2,3-dimethyl-2-pentene with HBr? (A) 1 (B) 2 (C) 3 (D) 4 (E) 8 ______ 14. What would be the major product of the reaction of α-phellandrene (a constituent of eucalyptus oil) with 9-BBN followed by hydrogen peroxide and base? A B C D OHOHOH OH ______ 15. Which of the following would be a major product of the ozonolysis of eugenol, a component of the smell of nutmeg, cinammon, and olives (shown at right)? H3CO HO A B C D H3CO H3CO O H3CO H3CO OOHOH HO HO HO HO Br ______ 16. If the product of the reaction of eugenol (shown above) with HBr yields the product shown to the right, what can be concluded? (A) HBr does not seem to react with benzene rings (B) There must be something more stable about the H3CO HO  secondary carbon next to the benzene ring than the secondary carbon to its right (C) That something might be the resonance in which the carbocation can participate  participate in with the benzene ring (D) All of the above ______ 17. What is the structure of (E)-3-tert-butyl-4-iso-propyl-3-hexene? A B C D ______ 18. What could be said about the reaction coordinate diagram to the right? ΔE(A) The dashed line represents  an exergonic reaction (B) The dashed line represents  a more stable product (C) The dashed line represents  a slower reaction (D) The dashed line is enthalpically, but not entropically, favored ______ 19. At pH 12 the only functional group that would have a charge is? (A) Alcohol (B) Amine (C) Carboxylic acid (D) Alkene ______ 20. The least stable chair conformation indicated below is: A B C DCH 2230 Fall 2014 Practice Exam #2 ANSWER KEY __D___ 1. Which of the following is the correct protonation state of the amino acid glycine at pH 12: (A) NH3+CH2COOH (B) NH3+CH2COO- (C) NH2CH2COOH (D) NH2CH2COO- __D___ 2. Which of the following alkene reactions can have carbocation rearrangements? (A) Hydrogenation (B) Hydroboration/oxidation (C) Halogenation (D) Hydration using water and acid __C___ 3. Which of the following alkene reactions proceeds through an anti mechanism? (A) Hydrogenation (B) Hydroboration/oxidation (C) Halogenation (D) Hydration using water and acid __A___ 4. Which product will result from the reaction of 1,2-dimethylcyclohexene with BH3 followed by treatment with H2O2 under basic aqueous conditions? A B C D H OH OH OH OH H HH __A___ 5. Which of the following structures does NOT have resonance structures? __D___ 6. Which of these is the least reasonable product of the reaction of 3-methybutene with water and sulfuric acid? OH OH A B C D OHOH __D___ 7. Which of the following molecules is most likely to undergo carbocation rearrangement during its reaction with HBr? A B C D __B___ 8. What is the stereochemistry of D-fructose (shown on right, carbon 6 is on bottom)? (A) (3R, 4R, 5S) (B) (3S, 4R, 5R) (C) (3R, 4S, 5S) (D) (3S, 4R, 5S) __B___ 9. What’s wrong with this mechanism? (A) Arrow is not following electrons (B) Electrons are moving from a nucleophile to a nucleophile (C) Electrons are moving from an electrophile to an electrophile (D) There is no carbocation rearrangement __A___ 10. What’s wrong with this mechanism? (A) Arrow is not following electrons (B) Electrons are moving from a nucleophile to a nucleophile (C) Electrons are moving from an electrophile to an electrophile (D) There is no carbocation rearrangement __D___ 11. Which of these molecules would undergo carbocation rearrangement upon reacting with HCl? A B C D __B___ 12. How many different products (including steroisomers) will form from the hydrogenation of 2,3-dimethyl-2-pentene? (A) 1 (B) 2 (C) 3 (D) 4 (E) 8 __D___ 13. How many different major products (including steroisomers) will form from the reaction of 2,3-dimethyl-2-pentene with HBr? (A) 1 (B) 2 (C) 3 (D) 4 (E) 8 __D___ 14. What would be the major product of the reaction of α-phellandrene (a constituent of eucalyptus oil) with 9-BBN followed by hydrogen peroxide and base? A B C D OHOHOH OH __B___ 15. Which of the following would be a major product of the ozonolysis of eugenol, a component of the smell of nutmeg, cinammon, and olives (shown at right)? H3CO HO A B C D H3CO H3CO O H3CO H3CO OOHOH HO HO HO HO Br __D___ 16. If the product of the reaction of eugenol (shown above) with HBr yields the product shown to the right, what can be concluded? (A) HBr does not seem to react with benzene rings (B) There must be something more stable about the H3CO HO  secondary carbon next to the benzene ring than the secondary carbon to its right (C) That something might be the resonance in which the carbocation can participate  participate in with the benzene ring (D) All of the above __A___ 17. What is the structure of (E)-3-tert-butyl-4-iso-propyl-3-hexene? A B C D __C___ 18. What could be said about the reaction coordinate diagram to the right? ΔE(A) The dashed line represents  an exergonic reaction (B) The dashed line represents  a more stable product (C) The dashed line represents  a slower reaction (D) The dashed line is enthalpically, but not entropically, favored __C___ 19. At pH 12 the only functional group that would have a charge is? (A) Alcohol (B) Amine (C) Carboxylic acid (D) Alkene __C___ 20. The least stable chair conformation indicated below is: A B C DUsing the ACS Study Guide, for the first semester exam, work the following problems: ∙ Nomenclature: 1, 3, 5, 7 ∙ Structure, Hybridization, Resonance, and Aromaticity: 1-8, 13 ∙ Acids and Bases: 1, 3, 4, 8, 10 ∙ Stereoisomerism: For questions 18, 19 a structure of tartaric acid would be  provided if such a question were on the actual exam ∙ Nucleophilic Substitutions and Eliminations: 1-12, 14, 15, 18, 19, 21-23, 25, 31 ∙ Electrophilic Additions: 1, 2, 4-8, 10-12, 16, 19 . . . . . . ∙ Spectroscopy: 2, 4, 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17

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