Organic Chemistry Questions

Place the answer in the blank Only answers in the blank will be graded Good luck The first to use the term polymer was a Wohler b Berzelius The synthesis of Nylon was invented at DuPont by a Wyeth b Carothers The compound Bakelite was a phenol formaldehyde resin developed by a Polanyi b Baekeland c Bakelite c Flory This compound invented in 1970 would eventually lead to liquid crystal polymers a Dacron b Ekonol c Nylon An example of a man made polymer is a Glycogen b Polystyrene An example of a biological polymer would be a Styrofoam b Bakelite An example of a linear polymer would be a Kevlar b Rubber An example of a branched polymer would be a PVC b Kevlar An example of a cross linked polymer would be a LDPE b PVC These compounds are macromolecules formed by covalent attachment of a set of small molecules a Dehydration b Polymers c Acids d Sugars An example of a network polymer would be a Rubber b LDPE c McIntire An example of polyethylene polymer could be found in a Carpet b Garden Hose An example of polypropylene polymer could be found in a Plastic bags b Plastic wrap c Proteins c Nylon 66 c LDPE c Rubber c Kevlar c PVC c Toys An example of polytetrafluoroethylene polymer could be found in a Plastic bottles b Plumbing parts c Cooking utensils c Carpeting An example of polyvinylchloride polymer could be found in a Carpeting b Plastic Toys d Dalton c Sewer pipe d Economy d Merrifield d Bakelite d Nucleic Acids d Starch d PVC d LDPE d Rubber d Kevlar d Cooking utensil d Bottles d Teflon d Cooking utensil

1 Show the reaction of benzoic acid with potassium hydroxide 2 Show the dehydration reaction of phthalic acid 3 Show the reaction of benzene with bromine 4 Show the reaction of ethane with hydrobromic acid 5 Show the reaction of sulfuric acid with calcium hydroxide

9 Here s an ugly molecule Make it look pretty OH

An example of a linear polymer would be a Kevlar b Rubber An example of a branched polymer would be a PVC b Kevlar An example of a cross linked polymer would a LDPE b PVC An example of a network polymer would be a Rubber b LDPE An example of polyethylene polymer could be found in a Carpet b Garden Hose c LDPE An example of polypropylene polymer could be found in a Plastic bags b Plastic wrap c Rubber c Kevlar c PVC c Toys An example of polytetrafluoroethylene polymer could be found in a Plastic bottles b Plumbing parts c Cooking utensils c Carpeting An example of polyvinylchloride polymer could be found in a Carpeting b Plastic Toys c Sewer pipe d PVC d LDPE d Rubber d Kevlar d Cooking utensil d Bottles d Teflon d Cooking utensil

Predict the product for the following reaction III CONV OF H NaBH CH3OH OH OH rot OH IV E OH OH

Predict the product for the following reaction O III OIV OI H NaBH CH3OH OH OH olo or OH OH IV OH

p dichlorobenzene Draw the structure for the following Be sure to show all hydrogen unless the presence is assumed as with short hand methods polystyrene Toluene o xylene C OH 3 chlorocylcohexene m dinitrobenzene polypropylene methyl benzene Benzyl bromide 8 4 Isopropyl benzene o bromotoluene styrene butadiene Coole 1 2 dichlorobiphenyl

a Select one Atomic Structure 2 Electronic Structure Question 1 Which statement describes patterns in how metals behave when forming ions a O Metals tend not to lose or gain any electrons O Metals tend to first lose and then gain electrons Metals tend to gain electrons O Metals tend to lose electrons

What reagents are the best choice for the transformation below O 1 PBr3 pyridine 2 NaCN O 1 HBr OH 2 NaCN O HCN O 1 TsCl pyridine 2 NaCN CN

t would you multiply moles of iodine by to get the units grams of iodine es I x grams I 1 mole I Use the References to access important values It ag and drop your selection from the following list to complete the answer 1 gram I 127 grams I 127 moles I

Select the lowest energy conformation for the following compound O A OB OC A B C D

Identify whether the overall reaction is oxidation reduction or neither O Oxidation Neither Reduction

Predict the major product of the following reaction A O A OB OC OD Br NaOH B OH OH a a C D E

Predict the major product of the following reaction CH8 x O A O B OC C C A Hg OAC MeOH NaBH NaOH Xa B OH you C D OH

O Catalytic hydrogenation of the following compound produces alkane The number of stereoisomer s formed is CH8 02 0 3 Pd C H

The following reaction proceeds and the product has a specific rotation of 4 1 If the enantiomeric excess is 3 8 calculate the optical rotation of pure S 3 methylhexanol O 1 079 O 1 079 10 Br II H O

Predict the major product of the following reaction the CH3 enantiomer A OA OB OC OH C H3O OH CH3 enantiomer B OH tym C D OH CH3

Predict the major product of the following reaction CH8 A LOH O A O O B C D H H O OH B C OH D OH E OH OH

Predict the major product of the following reaction CH7 A OA B OC B OH H SO4 H O C D SO H

Predict the major product s for the following reaction CH8 BH THF H O NaOH 3 A A B C D OH B OH OH dan OH D

Which of the given reaction schemes would produce the molecule shown below CH8 01 11 O III OI and II Ou Lu HBr ROOR 11 Br HBr HBr ROOR

Which of the following has the lowest vapor pressure O H O O NaCl O NH3 02 O CH4

Predict the major product s of the following reaction CH8 O A OB Br enantiomers A OC Br COOH COOH Br COOH Br Br CCIA enantiomers B Br COOH enantiomers C D Br

The freezing point of helium is approximately 270 C The freezing point of xenon is in the noble gas family Which of the following statements is supported by these data O Helium and xenon form highly polar molecules O As the molar mass of the noble gas increases the freezing point decreases O The London forces between the helium molecules are greater than the London forces between the xenon molecules O The London forces between the helium molecules are less than the London forces between the xenon molecules O none of these Question 7 The bonds between hydrogen and oxygen in a water molecule can be characterized as O hydrogen bonds O London forces O intermolecular forces 1 pts

Select the anticipated product s from the following solvolysis reaction CH7 OI SO IV OV Br OMe MeOH heat OM 5 IV

The following reaction will yields two products but the first step of the reaction goes through the same transition state TS1 structure Which one of the following structures corresponds to TS1 CH7 Br CH OH Free Energy la TS1 Br 8 Tal Br Tort I Reaction Coordinate OCH3 TS2 TS2

3 Calculate the pH and pOH of 0 2M NaOH solution NAOH is a strong acid 4Pts a pH

The energy diagram depicts the substitution reaction shown below Select the correct structure of intermediate III CH7 Free Energy O O OH CH OH H OH J Reaction Coordinate H CO

Predict the major product s of the following reaction CH7 COI Oll OIV Br OMe OI and II MeOH OMe E IV OMe

Precipitation titration is a method basedon complex formation due to reaction between metal ions cation and complexing agent ligand A True B False

Which of the statements below does concern the energy diagram of a reaction CH6 Free Energy Reaction Coordinate The rate determining step is the first step The rate determining step is the second step O The reaction goes through one transition state The reaction involves two intermediates

O 0 0413 M O 1 32 M O 0 528 M 0 184 M O 0 409 M 4 Question 32 You have two HCI solutions labeled solution A and solution B Solution A has a greater concentration than solution B Which of the following statements is are true O If you have equal volumes of both solutions solution B must contain more moles of HCI O If you have equal moles of HCI in both solutions solution B must have a greater volume O To obtain equal concentrations of both solutions you must add a certain amount of water to solution B 1 pts Adding more moles of HCL to both solutie will

What s wrong with the following mechanism CH6 0 O The arrow is backwards H 0 O There is no leaving group so there should be no arrows O An arrow is also needed to indicate the loss of a leaving group O The arrow should be removing a proton from the alpha carbon

Balance the following oxidation half reaction in acidic solution Te TeO Provide your answer below

Which two patterns of arrow pushing are seen in this reaction CH6 Br OH O Proton transfer and loss of a leaving group O Loss of a leaving group and nucleophilic attack Nucleophilic attack and rearrangement Rearrangement and proton transfer

Which of the following is the most likely structure of the following carbocation after rearrangment CH6 OI O II SO III IV

O dilute O saturated O supersaturated O concentrated O unsaturated Question 40 You have 25 00 mL of a 0 1000 M sugar solution How much water must be added to make a solution O200 2 mL O 3 12 mL O 21 9 mL O 175 2 mL 0 01249 M 1 pts

A scientist reacts some aluminum metal with some iron III oxide If the scientist actually measures 7 45g of aluminum oxide in the lab and they expected to generate 11 82g of aluminum oxide based on their calculations what is their percent yield Reaction 2Al s Fe2O3 aq Al2O3 aq 2Fe s

For the compound shown below rank the indicated protons in order of increasing acidity CH3 I H N HA O I ll III O I III II O III I II O III II I OH III OH 11

How many substituents does the following compound have CH4 Sed 02 O 3 04 O 5

Identify the equilibrium below that shows the two chair conformations of the following compound CH4 CI O O O O CI CI T CI CI CI C CI CI CI ZCI

What is a limiting reactant O The reactant which runs out first O The product that forms first All of these O The reactant which reacts the fastest The reactant which has some left over after a reaction

Which of the following is the correct wedge and dash conformation for the following Newman projection CH4 Br BU OI SO II O III O IV CI Br CI H H CH3 Et CI Br Br CI CI Br IV

What is the absolute configuration of the carbon marked with a and b CH5 HO A R B S O A S B R OA R B S OA S B R NH H gel N a S N IZ X O OH

Indicate which pattern of arrow pushing is involved in the reaction step shown CH6 H Proton transfer O Loss of a leaving group O Nucleophilic attack Carbocation rearrangement

Determine the pressure exerted by 2 94 mol of gas in a 2 92 L container at 32 C O2 64 atm O 73 6 atm 25 2 atm 7 72 atm

Choose the correct resonance hybrid of the following compound CH2 fo de la t 8 8 08 08 OA OB O C A O B 08 C 8 08 D

What is the correct IUPAC name of the following compound CH4 O 3 4 diisopropyl 5 pentyloctane O 3 4 di 1 methylethyl 5 pentyloctane O 3 ethyl 4 isopropyl 5 pentylnonane O 3 4 diisopropyl 7 methyl 5 propylnonane O 3 ethyl 4 isopropyl 2 7 dimethyl 5 propylnonane

Which of the following is the most stable isomer CH4 COI I SO II O III IV

What is the specific rotation of pure S carvone if a sample of R carvone of 78 ee has a specific rotation of 44 CH5 ee O 56 O 34 O 34 observed a a of pure enantiomer X 100