combined

Edit Mode is: ON• For Instructors Only Quizzes Preview Test: Quiz1_Ozonolysis_Chem332H

Preview Test: Quiz1_Ozonolysis_Chem332

Description Chem 332 Quiz#1-‐‑Ozonolysis (part of Exam#1)

Instructions

Timed Test This Test has the time limit of 2 hour. This Test will save and submit automatically when the time expires.

Warnings appear when half the time, 5 minutes, 1 minute, and 30 seconds remain.[The timer does not appear when previewing this

Test]

Multiple

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This Test allows multiple attempts.

Force

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Once started, this Test must be completed in one sitting.

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What is the missing product of this ozonolysis reaction?

A. Formaldehyde

B. Acetic acid

C. Acetaldehyde

D. Acetone

E. carbon dioxide

Question 1 0.5 points Save Answer

Which ozonide intermediate would result from the ozonolysis of styrene (vinylbenzene, C6H5CH=CH2)?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of these.


?

Question Completion Status:

Which of the compounds (below) yields isopropanol as one of the products of 1) ozonolysis + 2) NaBH4 workup ?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of these compounds


Which of the compounds (below) yields 2-butanone as one of the products of 1) ozonolysis + 2) workup with DMS ?

A. Compound A

B. Compound B

C. Compound C

D. Compound D



Which compound forms carbonic acid under ozonolysis conditions with an oxidative workup with peroxide inacid?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E


Which compound is the least reactive under ozonolysis conditions with an oxidative workup with peroxide inacid?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E


Which molozonide will form formaldehde under ozonolysis conditions ?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E


Which ozonide will form formaldehde under ozonolysis conditions ?



A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E

Which ONE statement (below) is NOT true about the ozonolysis reaction.

A. Cyclic ketones can never be formed.

B. Cycloalkenes can undergo ozonolysis

C. Formation of a molozonide is a concerted process.

D. Aldehydes might be formed

E. Ozone is a 1,3-‐‑dipole


Which ONE is NOT used as a Reagent in the workup conditions of an ozonolysis reaction that produces analdehyde.

A. Acetic Acid

B. Zinc metal

C. Vinegar

D. DMSO

E. CH3-‐‑S-‐‑CH3


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Edit Mode is: ON• Course Content Quizzes for Exam 1 Preview Test: Quiz2_Conjugation_Chem332H

Preview Test: Quiz2_Conjugation_Chem332

Description Chem 332 Quiz#2 (part of Exam#1)

Instructions



Test]

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Which structure is NOT conjugated ?

A.Compound A

B. Compound B

C.Compound C

D.Compound D

E. Compound E


Which Structures are conformers?

A. Structure A and Structure D

B. Structure A and Structure E

C. Structure B and Structure E


?


C. Structure B and Structure E

D. Structure C and Structure E

E. Structure A and Structure C

Which diene is in the s-cis conformation AND in an (E) and (Z) configuration?

A. Structure A

B. Structure C

C. Structure B

D. Structure D

E. Structure E


Which conjugated diene is currently in an s-cis conformation ?

A. Compound A

B. Compound B

C. Compound C

D. Compound D



Which conjugated diene is currently in an s-trans conformation ?


A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E

Which resonance forms represent the intermediate carbocation that will produce the kinetic and thermodynamic products in this

addition reaction?

A. Structure B and Structure E

B. Structure A and Structure D

C.Structure C and Structure D

D. Structure B and Structure D

E. Structure B and Structure C


Which ONE statement is True about the addition reaction shown below?

A. The 1,4-‐‑addition product is shown and the major product under thermodynamic control.

B. The 1,4-addition product is shown and the major product under kinetic control.

C. The 1,2-‐‑addition product is shown and the major product under thermodynamic control.


D.The 1,2-addition product is shown and the favored product under kinetic control.

Which ONE statement is True about the addition reaction shown below?

A. The 1,4-addition product is shown and the major product under kinetic control.

B. The 1,2-addition product is shown and the favored product under kinetic control.

C. The 1,2-‐‑addition product is shown and the major product under thermodynamic control.

D. The 1,4-‐‑addition product is shown and the major product under thermodynamic control.


Which ONE statement is True about the overall reaction shown below?

A. This is the Cope Rearrangement, which in this case, favors the production of a more conjugated system.

B. This is the Diels-Alder Reaction, which requires one of the reactants to be an s-cis diene.

C. This is the Cope Rearrangement, which requires the reactant to be conjugated.

D. This is the Cope Rearrangement, which produces a product that is a conformational change.

E. This is the Diels-‐‑Alder Reaction, which is a 6-‐‑electron, concerted process.


Which ONE compound is major product of this reaction?

A. 2,5-‐‑dimethyl-‐‑1,5-‐‑hexadiene

B. 2,5-‐‑dimethyl-‐‑2,4-‐‑hexadiene

C. 2,5-‐‑dimethyl-‐‑1,4-‐‑hexadiene

D. (Z)-‐‑2,5-‐‑dimethyl-‐‑1,3-‐‑hexadiene

E. (E)-‐‑2,5-‐‑dimethyl-‐‑1,3-‐‑hexadiene



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Edit Mode is: ON• Course Content Quizzes for Exam 1 Preview Test: Quiz3_DielsAlder_Chem332H

Preview Test: Quiz3_DielsAlder_Chem332

Description Chem 332 Quiz#3-‐‑DielsAlder (part of Exam#1)

Instructions



Test]

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Choose the structures of the starting diene and dienophile necessary to prepare this molecule?

A.

B.

C.

D.


Which of the compounds will react as a diene in a Diels-Alder reaction?

A. Compound A

B. Compound B


?


B. Compound B

C. Compound C

D. Compound D

E. None of these Compounds.

Which compound can react as a diene in a Diels-Alder reaction?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of these Compounds


Identify the diene and dienophile which would give the Diels Alder product shown.


A. Reagents A

B. Reagents B

C. Reagents C

D. Reagents D

E. None of these.

Which compound CANNOT react as a diene in a Diels-Alder reaction?

A. Compound A

B. Compound B

C. Compound C

D. Compound D



Identify the diene used in the reaction shown above.

A. Compound A

B. Compound B

C. Compound C

D. Compound D



What is the product of the reaction shown below?

A. Compound A

B. Compound B

C. Compound C

D. Compound D




Which conjugated diene would react the fastest with maleic anhydride?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E

Which structure (A-E) represents the product of this reaction?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E


Which structure (A-E) represents the product of this reaction?

A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. Compound E



E. Compound E

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Edit Mode is: ON• Course Content Quizzes for Exam 1 Preview Test: Quiz4_Alcohols_Chem332H

Preview Test: Quiz4_Alcohols_Chem332

Description Chem 332 Quiz#2 Alcohols -‐‑ Part of Exam#1

Instructions



Test]

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Choose the best set of reagents for carrying out the chemical conversion (below).

A. 1) TMS-‐‑Cl, Et3N

2) MeMgBr, ether

3) H3O+

B. None of these Reagent Sets.

C. 1) NaBH4, MeOH

2) MeOH

D. 1) PBr3

2) MeOH

E. 1) LiAlH4, ether

2) H3O+

3) MeMgBr, ether

4) H3O+


Give the common names for each of these compounds.

A. allyl alcohol

ethylene glycol


?


ethylene glycol

ethanol

hydroquinone

B. vinyl alcohol

propylene glycol

ethanol

quinone

C. vinyl alcohol

ethylene glycol

ethanol

hydroquinone

D. allyl alcohol

propylene glycol

ethanol

quinone

The best reagents for accomplishing this transformation are:

A. 1) Hg(OAc)2, H2O

2) NaBH4

B. 1) BH3, THF

2) H2O2, -‐‑OH

C. 1) OsO4, pyridine

2) NaHSO4, H2O

D. 1) m-‐‑CPBA, CH2Cl2

2) H3O+

E. None of these Reagent Sets.


A highly useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonylcompounds. Show what Grignard reaction would NOT be used to prepare the alcohol (below).


A. Reactants A

B. Reactants B

C. Reactants C

D. Reactants D

Give the major organic product for the reaction below.

A. Compound A

B. Compound B

C. Compound C

D. Compound D




A. Compound A

B. Compound B

C. Compound C

D. Compound D



A. Compound A

B. Compound B

C. Compound C

D. Compound D



Give the major organic product from the reaction below.


A. Compound A

B. Compound B

C. Compound C

D. Compound D



A. None of these Reagent Sets.

B. 1) TMS-‐‑Cl, Et3N

2) MeMgBr, ether

3) H3O+

C. PCC, CH2Cl2

D. 1) NaBH4, ethanol

2) H3O+

E. 1) LiAlH4, ether

2) H3O+



A. 1) NaBH4, ethanol



1) NaBH4, ethanol

2) H3O+

B. 1) TMS-‐‑Cl, Et3N

2) MeMgBr, ether

3) H3O+

C. None of these Reagent Sets.

D. PCC, CH2Cl2

E. 1) PBr3

2) NaOH

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Edit Mode is: ON• For Instructors Only Quizzes Preview Test: Quiz5_Aldehydes and Ketones_Chem332H

Preview Test: Quiz5_Aldehydes and Ketones_Chem332


Instructions



Test]

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Completion



What functional group results from the reaction shown below?

A. aldehyde

B. carboxylic acid

C. alcohol

D. conjugated diene

E. ketone



A. Compound A

B. Compound B

C. Compound C

D. Compound D




?


What is the best reagent to use for the reaction shown below?

A. 1) NaBH4, ethanol 2) H3O+

B. NaCN, DMSO

C. NaOH, methanol, heat

D. 1) CH2=P(Ph)3 2) H3O+

E. PCC


Which of the compounds below is an acetal?

A. Compound A

B. Compound B

C. Compound C

D. Compound D



What is the product of the reaction below?

A. 3-‐‑methylpentane

B. 3-‐‑methyl-‐‑1-‐‑pentyne

C. 3-‐‑methylhexane

D. 3-‐‑methyl-‐‑2-‐‑pentanol

E. 3-‐‑methyl-‐‑2-‐‑pentene




A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of these Conpounds


What are the products of the reaction shown below?

A. cyclohexanone and ethanol

B. cis-‐‑1,2-‐‑cyclohexanediol and ethanol

C. trans-‐‑1,2-‐‑cyclohexanediol and ethanol

D. cyclohexanone and ethanal

E. cis-‐‑1,2-‐‑cyclohexanediol and ethanal



A. 4-‐‑methyl-‐‑1-‐‑pentene

B. 1-‐‑pentene

C. 2-‐‑methyl-‐‑1-‐‑hexene

D. 2-‐‑methyl-‐‑1-‐‑pentene



E. 2-‐‑methyl-‐‑2-‐‑propyloxirane

Identify the missing reagent for the reaction shown below.

A. Compound A

B. Compound B

C. Compound C

D. Compound D



What is the product of the reaction sequence shown below?

A. 2-‐‑methyl-‐‑2-‐‑hexene

B. 2,3-‐‑dimethyl-‐‑2-‐‑pentene

C. 2-‐‑methyl-‐‑1-‐‑hexene

D. 3-‐‑methyl-‐‑1-‐‑hexene

E. 2-‐‑methyl-‐‑1-‐‑pentene


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Edit Mode is: ON• Course Content Quizzes for Exam 2 Preview Test: Quiz6_Carboxylic Acids_Chem332H

Preview Test: Quiz6_Carboxylic Acids_Chem332


Instructions


Warnings appear when half the time, 5 minutes, 1 minute, and 30 seconds remain.[The timer does not appear when previewing this Test]

Multiple Attempts This Test allows multiple attempts.

Force Completion Once started, this Test must be completed in one sitting.


Choose the BEST reagent(s) for carrying out the reaction below.

A. 1. BH3 2. H3O+

B. NaBH4, ethanol

C. acid, water, heeeet

D.Tollens’ Reagent

E. CH3I


Which reagent CANNOT ever be used on an aldehyde to produce a carboxylic acid?

A. the oxygen in air + water

B. Ag2O + base

C. hydrogen peroxide

D. The Silver Mirror Test

E. LAH


Name the compounds below.

A. 3-‐‑propylpentanoic acid

4-‐‑hydroxy-‐‑3-‐‑methylbutanoic acid

2-‐‑bromo-‐‑4-‐‑ethylbenzenecarboxylic acid

B. 3-‐‑ethylhexanoic acid


4-‐‑ethylbenzenecarboxylic acid

C. 3-‐‑propylpentanoic acid

3-‐‑(hydroxymethyl)butanoic acid


D. 3-‐‑ethylhexanoic acid


2-‐‑bromo-‐‑meta-‐‑ethylbenzenecarboxylic acid


?


E. 3-‐‑ethylhexanoic acid



Which structure below is the tetrahedral intermediate in the acid-catalyzed Fischer esterification reaction of acetic acid, CH3CO2H, and ethanol,CH3CH2OH?

A. A

B. B

C. C

D. D

E. None of these structures


See the oxygen atom (with the red arrow) in the ethanol structure over the equilibrium arrow? Which Fischer Esterification product has anarrow correctly pointing at that same oxygen?

A. Structure A

B. Structure B

C. Structure C

D. Structure D

E. None of the Structures


Identify the lactone resulting from the INTRAmolecular Fischer-‐‑Esterification of the compound shown below.


A. Structure A

B. Structure B

C. Structure C

D. Structure D

E. None of the Structures

To convert a nitrile to a carboxylic acid, as shown below, you need to:

A. reduce with H2

B. hydrolyze with aqueous acid (H3O+) and heat.

C. reduce with LiAlH4

D.oxidize with Ag+

E. add a Grignard reagent


Choose the BEST reagent(s) for carrying out the reaction below.

A.O3, then Zn and HOAc

B. 1. Mg, ether 2. CO2 3. H3O+

C. KMnO4 under basic conditions with heat

D.1. NaCN 2. H2SO4, H2O, heat

E. Tollens’ Reagent


Which carboxylic acid has the highest boiling point?

A. glycolic acid

B. butanoic acid

C. 2-‐‑hydroxypropanoic acid



D. propionic acid

E. α-‐‑hydroxybutyric acid

What are the names of these carboxylic acids?

A. glycolic acid

lactic acid

α-‐‑methylbutyric acid

B. 1-‐‑hydroxypropionic acid

glycolic acid

α-‐‑methylbutanoic acid

C. 2-‐‑hydroxypropanoic acid

salicylic acid


D. glycolic acid

2-‐‑hydroxyethanoic acid


E. glycolic acid

lactic acid

1-‐‑methylbutyric acid


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Edit Mode is: ON• Course Content Quizzes for Exam 2 Preview Test: Quiz7_Enols-‐‑Enolates_Chem332H

Preview Test: Quiz7_Enols-‐‑Enolates_Chem332


Instructions

Timed Test This Test has the time limit of 2 hour. You are notified when time expires, and you may continue or submit.


Multiple Attempts This Test allows multiple attempts.

Force Completion Once started, this Test must be completed in one sitting.


Rank the hydrogens (in the compound below) in order of decreasing acidity (most acidic proton listed first). Be careful, this question is a classic MCAT question and is harder that you might think. Keep track of ALL the alpha protons. (~Dr. K.).

A. Ha > Hb > Hc ≈ Hd

B. Ha > Hb ≈ Hc > Hd

C. Hb > Ha ≈ Hd > Hc

D. Ha > Hb ≈ Hd > Hc

E. Ha ≈ Hb > Hc ≈ Hd


Rank the compounds below in order of decreasing acidity (compound with the most acidic proton should be listed first).

A. III > II > I

B. II > III > I

C. II > I > III

D. I > II > III

E. I > III > II


Which one of the following compounds has two different enol forms?

A. 2,2-dimethylcyclohexanone

B. 3,3-dimethylcyclohexanone

C. 4,4-dimethylcyclohexanone


?


4,4-dimethylcyclohexanone

D.cyclohexanone

How many alpha hydrogens are there on 2,4-dimethyl-3-pentanone?

A. four (4)

B. None

C. six (6)

D. three (3)

E. two (2)


Alkylation with methyl iodide of the kinetic enolate of the compund shown below produces which product?

A. Compound A

B. Compound B

C. Compound C

D. Compound D


Which one of the following cannot form an enolate anion? Look at your lecture notes on enolate formation (~ Dr. K.)

A. 2,3-dimethylbutanal

B. 2,2-dimethylbutanal

C. 2-ethylbutanal

D.3,3-dimethylbutanal




A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of the Compounds

Arrange the compounds (below) in order of decreasing acidity (most acidic compound listed first).

A. III > II > I

B. II > III > I

C. III > I > II

D. I > II > III


Which one of the optically active compounds (below) racemizes (loses all optical activity) in dilute KOH/CH3OH solution? Start by drawing the tautomerization mechanism, while looking at what happens to the chiral center. - Dr. K.

A. Compound A

B. Compound B

C. Compound C

D. Compound D


Identify the major organic product of the above reaction.



A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of the Compounds

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Edit Mode is: ON• Course Content Quizzes for Exam 2 Preview Test: Quiz8_EnolateAlkylations_Chem332H

Preview Test: Quiz8_EnolateAlkylations_Chem332

Description Chem 332 Quiz#8-‐‑Enolate Alkylations -‐‑ Part of Exam 2.

This Quiz is due (to be submitted online) before Sunday (03/09/2014) at Noon (12pm).You may submit this quiz as many times as you wish -‐‑ knock yourselves out. Your Highest Score will be recorded. Use this Quiz to identify the topics that cause you trouble.

These Quiz questions are meant to give you feedback on how well you are digesting the course material -‐‑ before you take the exam. Submit your Quiz results before the end

of the 2-‐‑hour time limit AND before the listed deadline.

You should see your grade on the Compass 2G Grade Book immediately upon submitting your Quiz answers. Make sure to confirm that Compass actually awarded you the

Quiz Points.

Instructions



Multiple

Attempts


Force

Completion



Predict the product from the reaction sequence (below).

A. Compound A

B. Compound B

C. Compound C

D. Compound D


What gas evolves at the end of the acetoacetic ester sequence?

A. H2

B. SO2

C. carbon dioxide

D. oxygen

E. H2O vapor


Which of the following is used in the enolate chemistry shown below?


?


A. Compound A

B. Compound B

C. Compound C

D. Compound D

Name the compounds.

A. malaeic anhydride, enol of acetone, LDA, Sodium acetate & acetoacetic ester

B. diethyl malonate, enolate of acetone, LDA, Sodium Ethoxide & ethyl acetoacetate

C. ethyl acetoacetate, enolate of acetone, LDS, Sodium Ethoxide & ethyl acetoacetate

D. diethyl malonate, enol of acetone, LSD, Sodium acetate & acetoacetic ester

E. diethyl malonate, enol of acetone, LDA, Sodium Ethoxide & ethyl acetoacetate


Lithium diisoproylamide is a _________

A.weak base that only attacks protons on polar O-H bonds.

B. good nucleophile, but cannot attack protons alpha to a carbonyl group.

C. sterically hindered base, which is a great nucleophile that adds to carbonyl functional groups.

D. "baby hydride", which attacks protons at the less sterically crowded side of the compound.

E. sterically hindered base, which attacks alpha protons at the less sterically crowded side of the compound.


Give the major organic product of the reaction (below).


A. Compound A

B. Compound B

C. Compound C

D. Compound D


Give the major organic product of the reaction (below).

A. Compound A

B. Compound B

C. Compound C

D. Compound D



Give the major organic product of the reaction (below) done at RT (room temperature).

A. Compound A

B. Compound B

C. Compound C

D. Compound D



In the acetoacetic acid synthesis (shown below), which one of the following electrophiles is used?

A. Compound A



A. Compound A

B. Compound B

C. Compound C

D. Compound D

E. None of these Componds.

Alkylation with methyl iodide of the kinetic enolate of the compound (shown below) produces which product?

A. Compound A

B. Compound B

C. Compound C

D. Compound D



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Edit Mode is: ON• Course Content Quizzes for Exam 2 Preview Test: Quiz9_AldolClaisen_Chem332H

Preview Test: Quiz9_AldolClaisen_Chem332

Description Chem 332 Quiz#9-‐‑AldolClaisen -‐‑ Part of Exam 2.

This Quiz is due (to be submitted online) before Sunday (03/09/2014) at Noon (12pm).You may submit this quiz as many times as you wish -‐‑ knock yourselves out. Your Highest Score will be recorded. Use this Quiz

to identify the topics that cause you trouble. These Quiz questions are meant to give you feedback on how well you are

digesting the course material -‐‑ before you take the exam. Submit your Quiz results before the end of the 2-‐‑hour time limit

AND before the listed deadline.

You should see your grade on the Compass 2G Grade Book immediately upon submitting your Quiz answers. Make sure to

confirm that Compass actually awarded you the Quiz Points.

Instructions



Multiple

Attempts


Force

Completion



Consider the reaction below and select the the best answer:

A. B forms a nucleophilic enolate; A is the electrophile; C is the base.

B. Both A and C are the electrophiles; B is the nucleophile.

C. A forms a nucleophilic enolate; B is the electrophile; C is the base.

D. Both A and B are the electrophiles; C is the nucleophile.

E. Dr. K. is making-‐‑up this reaction; A isn't even a real compound; and C is the base.


What is the aldol self-addition product of propanal?

A. 4-hydroxyhexanal

B. 5-hydroxyhexanal

C. 2-hydroxy-2-methylpentanal

D.3-hydroxy-2-methylpentanal

E. 3-hydroxyhexanal


?


E. 3-hydroxyhexanal

Benzalacetone is the crossed aldol condensation product formed between benzaldehyde and acetone. Which of the structures(below) is of benzalacetone? Remember the difference between a condensation product and an addition product. ~ Dr. K.

A. Compound A

B. Compound B

C. Compound C

D. Compound D



Which is the product of this intramolecular aldol condensation reaction?

A. Compound A

B. Compound B

C. Compound C

D. Compound D




Identify the starting reactant needed to make the cyclic ketone product (shown below) by an intramolecular aldolcondensation reaction.

A. Compound A

B. Compound B

C. Compound C

D. Compound D



Identify the starting reactants needed to make the product (shown below) by a mixed aldol condensation.

A. acetophenone (methyl phenyl ketone) and butanal

B. acetophenone (methyl phenyl ketone) and 2-butanone

C. benzaldehyde (C6H5CH=O) and 2-pentanone

D.benzaldehyde (C6H5CH=O) and 3-pentanone


Which of the following is the Claisen self-condensation product of ethyl propanoate, CH3CH2CO2Et ?


A. Compound A

B. Compound B

C. Compound C

D. Compound D


Identify the missing reactant in the reaction shown below. Knowing the product is a 1,3-keto ester should help.Study your reactions by covering each reactant in your lecture notes and determine the reactant structure. Dr. K.

A. ethyl acetate, CH3CO2Et

B. diethyl oxalate, EtO2CCO2Et

C. Carbonic Acid, HOCO2H

D.ethyl formate, HCO2Et

E. diethyl carbonate, (EtO)2C=O


Which one of the following cannot give a Claisen condensation product?

A.H2C=CHCH2CH2CO2Et

B. (CH3)3CCO2Et

C.C6H5CH2CO2Et

D. (CH3)3CCH2CO2Et

E. (CH3)2CHCH2CO2Et


Which of the following is the product of the reaction sequence shown below?



A. 4-methyl-3-hexanone

B. 4-octanone

C. 4-heptanone

D.2-ethylpentanoic acid

E. 2-propylbutanoic acid

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Edit Mode is: ON• Course Content Quizzes for Exam 2 Preview Test: Quiz10_MichaelEnamineRobinson_Chem332H

Preview Test: Quiz10_MichaelEnamineRobinson_Chem332

Description Chem 332 Quiz#10-‐‑MichaelEnamineRobinson -‐‑ Part of Exam 2.

This Quiz is due (to be submitted online) before Sunday (03/09/2014) at Noon (12pm).You may submit this quiz as many times as you wish -‐‑ knock yourselves out. Your Highest Score will be recorded. Use

this Quiz to identify the topics that cause you trouble. These Quiz questions are meant to give you feedback on how well

you are digesting the course material -‐‑ before you take the exam. Submit your Quiz results before the end of the 2-‐‑hour

time limit AND before the listed deadline.

You should see your grade on the Compass 2G Grade Book immediately upon submitting your Quiz answers. Make sure

to confirm that Compass actually awarded you the Quiz Points.

Instructions



Test]

Multiple

Attempts


Force

Completion



Which carbon atoms are most susceptible to nucleophilic attack AND which carbon would be attacked by a cuprate ?

A. II and III -a cuprate would add at carbon IV

B. II and III -a cuprate would add at carbon II

C. II and IV -a cuprate would add at carbon II

D. II and IV -a cuprate would add at carbon IV

E. III and IV -a cuprate would add at carbon IV


Which one of the following reagents adds a methyl group by conjugate (1,4-addition) addition to an α,β-unsaturatedketone or aldehyde?

A. (CH3)2CuLi


?


A. (CH3)2CuLi

B. CH3MgBr

C. LAH

D.CH3Li

E. Hg(OAc)2

Heating a mixture of 1,3-diphenylacetone and acrolein with a weak base gives a product, C18H16O, in 53% yield. Themechanism for product formation is a Michael addition followed by an intramolecular aldol condensation. Which of theabove structures is the product of this reaction?Also, as a side question, do you know the Name Reaction for this reaction sequence? ~Dr. K.

A. Compound A

B. Compound B

C. Compound C

D. Compound D



A Robinson annulation reaction is shown below. Identify the missing reagent in the first step.

This is just ONE Name Reaction done backwards. Could you do this problem if it wasn't identified as a Robinson Annulation? How about if the possible answers weren't visible?How about if it was in a 2-reaction sequence?~ Dr. K.

A. Compound A


Compound A

B. Compound B

C. Compound C

D. Compound D


The Stork Enamine reaction is a Michael addition on an enone.Predict the product of the reaction sequence (shown below).

A. Compound A

B. Compound B

C. Compound C

D. Compound D



To make this compound (below), you need:Select the BEST answer available

A. Gilman Reagent and an enone

B. An enamine and a ketone

C. Gilman Reagent and an enamine

D. MethylGrignard and an enone

E. Gilman Reagent and a ketone



What just happened here ??

A. Conjugate (Michael) Addition + Robinson Annulation

B. Direct (1,2-‐‑) Addition + Aldol

C. Conjugate (Michael) Addition + Aldol

D. Direct (1,2-‐‑) Addition + Claisen

E. Conjugate (Michael) Addition + Dieckmann

How can you make a 1,4-‐‑dicarbonyl compound?

A. Gilman Reagent + Aldehyde

B. Enamine + α-‐‑bromoester

C. Enamine + Enone

D. Cuprate + Ester

E. Enolate + enone


How can you make a 1,5-‐‑dicarbonyl compound?

A. Enamine + Alkylhalide

B. Cuprate + Ester

C. Gilman Reagent + Aldehyde

D. Enolate + enone

E. Enamine + α-‐‑bromoester


How can you make a cyclohexenone?

A. Dieckmann

B. Robinson

C. Michael

D. Hell-‐‑Volhardt-‐‑Zelinski

E. Aldol


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Preview Test: Quiz11_AminePreps_Chem332

Test InformationDescription Chem 332 Quiz#11-Amine Preps - Part of Exam 3.

InstructionsTimed Test This test has a time limit of 2 hours.This test will save and submit automatically when the time expires.

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Select the name for this compound below.

QUESTION 10.5 points Save Answer

0.5 points Save Answer


https://compass2g.illinois.edu/webapps/assessment/take/launch.jsp?course_assessment_id=_42978_1&course_id=_13668_1&content_id=_1098991_1&step=null#

A. N,N-diethyl-2-pentanamine

B. N,N-diethyl-1-methylbutanamine

C.N,N-diethyl-3-pentanamine

D. N,N-diethyl-4-pentanamine

E. N-ethyl-4-methyl-3-hexanamine

Which must have a higher boiling point (bp) than N,Ndimethyl2hexanamine ?(Select the BEST answer based on your knowledge of the relationshipbetween structure and bp)

A. all tertiary amines

B. secondary amine with lower mol. weight (fewer carbons)

C.secondary amine with higher mol. weight (more carbons)

D. tertiary amine with lower mol. weight (fewer carbons)

E. all amines with at least six total carbons

QUESTION 2

The compound below is classified as a(n):

QUESTION 3



A. secondary amine.

B.amide.

C.arylamine

D. tertiary amine.

E. primary amine.

What is the product of the reaction sequence shown below ?

QUESTION 4


A. Compound A

B. Compound B

C.Compound C

D. Compound D



QUESTION 5


A. Compound A

B. Compound B

C.Compound C

D. Compound D


What is the product of the reaction shown below ?

QUESTION 6

A. Compound A

B. Compound B

C.Compound C

D. Compound D



QUESTION 7



A. Compound A

B. Compound B

C.Compound C

D. Compound D



QUESTION 8


A. Compound A

B. Compound B

C.Compound C

D. Compound D


The structure of heroin is shown below.Which ONE phrase is NOT true about this compound?

QUESTION 9


A. tertiary amine

B. opioid

C.can be derived from morphine

D. major component of poppy pods

E. highly addictive / habit forming

Which is NOT True about N-ethylaniline ?A. chiral at very low temperatures

B. sp3 hybridized nitrogen

C.cannot form hydrogen bonds

D. secondary amine

E. arylamine

QUESTION 10

Preview Test: Quiz12_AmineRxns_Chem332

Test InformationDescription Chem 332 Quiz#12-AmineRxns - Part of Exam 3.


Warnings appear when half the time, 5 minutes, 1 minute, and 30 seconds remain.[The timer does not appear whenpreviewing this test]

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What is the product of the reaction sequence shown below?





A. Compound A

B. Compound B

C.Compound C

D.Compound D

What is the major product of the reaction sequence below ?

A. Compound A

B. Compound B

C.Compound C

QUESTION 2


D.Compound D

Which is true about the basicity of the nitrogen lone pairs in the compound below?

A. The alkyl amine is more basic than the imine

B. The heterocyclic amine is more basic than the imine

C.The sp2 hybridized amine is the most basic

D.The imine is the most basic

E. The secondary amine is the most basic

QUESTION 3

Which ONE answer most accurately describes the Structures (below)?

A. Structure 1 is a nitrite ion

B. Structure 3 is a nitrosamine

C.Structure 2 is a nitrosonium ion

D.Structure 1 is a nitrosonium ion

E. Structure 2 is diazo compound

QUESTION 4


Which ONE answer most accurately describes the Structures (below)?

QUESTION 5


A. Structure 1 is a diazonium ion

B. Structure 3 is a nitrite ion

C.Structure 2 is a nitrosonium ion

D.Structure 2 is a nitrosamine

E. Structure 3 is a diazonium ion

Which ONE answer most accurately ranks the basicity of subtituted anilines ? (Most basic compound on the left / Least basic compound on the right)

A. 4-methoxyaniline > p-nitroaniline > p-chloroaniline

B. 4-methoxyaniline > p-chloroaniline > p-nitroaniline

C.p-nitroaniline > p-chloroaniline > 4-methoxyaniline

D.4-cyanoaniline > p-methoxyaniline > p-nitroaniline

E. 4-cyanoaniline > p-chloroaniline > p-nitroaniline

QUESTION 6


Which ONE answer most accurately lists the reaction steps for this transformation ?

A. 1)Sn+HCl 2)HONO+HCl 3)copper(I)chloride

B. 1)H2-Pd/Carbon 2)reductive amination 3)copper(I)chloride

QUESTION 7



C.1)hydrogenation 2)diazotization 3)Sandmeyer

D.1)hydrogenation 2)nitrosation 3)Sandmeyer

E. 1)Sn+HCl 2)nitrosation 3)copper(I)oxide

Which ONE answer most accurately lists the reaction steps for this transformation ?

A. 1)Sn+HCl 2)HONO+HCl 3)copper(I)chloride

B. 1)hydrogenation 2)dialkylation 3)Sandmeyer

C.1)H2-Pd/Carbon 2)reductive amination 3)copper(I)chloride

D.1)Sn+HCl 2)nitrosation 3)copper(I)oxide

E. 1)hydrogenation 2)nitrosation 3)Sandmeyer

QUESTION 8

What is the product of the reaction sequence shown below ?This question is the most difficult of the entire quiz. So, here is a hint: This is a Name Reaction where the proton on the least hindered side of the ring is removed.Dr. K.

QUESTION 9



A. Compound A

B. Compound B

C.Compound C

D.Compound D



QUESTION 10

A. Compound A

B. Compound B

C.Compound C

D.Compound D


Preview Test: Quiz13_AminoAcids_Chem332

Test InformationDescription Chem 332 Quiz#13-AminoAcids - Part of Exam 3.

InstructionsTimed Test This test has a time limit of 2 hours.You will be notified when time expires, and

you may continue or submit.Warnings appear when half the time, 5 minutes, 1 minute, and 30seconds remain.[The timer does not appear when previewing this test]

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Humans are able to synthesize only 10 of the 20 common amino acids necessary for protein synthesis. The remaining 10 are called __________amino acids since they must be obtained from dietary sources.

A. deficient

B.nonessential

C.dietary

D.complex

E. essential


QUESTION 2


Question CompletionStatus:


Given the pKa data below, select the one statement that is most true.

A. Asparagine has a net positive charge in pH 5.4 buffer

B.Arginine has a net negative charge in pH 5.4 buffer

C.Alanine is exclusively a zwitterion in pH 9.9 buffer

D.Arginine side chain is polar acidic

E. Asparagine has a net neutral charge in pH 5.4 buffer

QUESTION 2

Given the pKa data below, select the one statement that is most true.

A. Asparagine has a net neutral charge in pH 8.8 buffer

QUESTION 3



B.Arginine has a net positive charge in pH 5.4 buffer

C.Asparagine has a polar basic side chain

D.Alanine is has a net positive charge in pH 6.1 buffer

E. Arginine has a net neutral charge in pH 5.4 buffer

Which of the compounds below is the zwitterion form of alanine?

A. Compound A

B.Compound B

C.Compound C

D.Compound D

QUESTION 4

Glutamic Acid (structure shown below with pKa values), has a pI of?

QUESTION 5



A. 6.96

B.7.0

C.5.37

D.3.22

E. 5.93

The Fischer projection shown below denotes a ______ amino acid which has the _____ configuration.

A. L, S

B.L, R

C.D, R

D.D, S

QUESTION 6

Which amino acid CANNOT be formed from this synthetic method?

A. Leucine

Glycine

QUESTION 7



B.C.Proline

D.Valine

E. Alanine

Which amino acid CANNOT be formed from this synthetic method?

A. Valine

B.Leucine

C.Phenylalanine

D.Glycine

E. Alanine

QUESTION 8

Which reactant is needed for the synthesis of alanine using reductive amination?Select the one best answer.

A. BINAP catalyst

B.acetaldehyde

C.enamido acid

QUESTION 9



D.pyruvic acid

E. Nacetylated enamine

Which reactant is needed for the synthesis of alanine using the Strecker synthesis ?Select the one best answer.

A. BINAP catalyst

B.Nacetylated enamine

C.acetaldehyde

D.pyruvic acid

E. enamido acid

QUESTION 10

Preview Test: Quiz14_Peptides_Chem332

Test InformationDescription Chem 332 Quiz#14-Peptides - Part of Exam 3.


Warnings appear when half the time, 5 minutes, 1 minute, and 30 seconds remain.[The timer does notappear when previewing this test]

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Which one answer is the abbreviated formula of the peptide shown below?Hint: Identify the amide bonds, then identify each amino acid. ~ Dr. K.

A. lysseraspala

B. serlysalaasp

C.aspalaserlys

D.aspseralalys





E. aspalasertyr

Which one answer Best describes the structure shown below?

A. tBocPhePro

B.FmocPhePro

C.FmocProPhe

D. tBocProPhe

E. tBocAlaPro

QUESTION 2

Which one answer Best describes the structure shown below?

A. FmocLys

B.Nacyl FmocLys

C.Nacyl tBocArg

D.Nacyl tBocLys

Nacyl FmocArg

QUESTION 3



E.

Which one answer Best describes the product that forms when the compound below is treated with ammonia?

A. tBocGlu

B.FmocLys

C.FmocArg

D. tBocLys

E. FmocGlu

QUESTION 4

Which one answer describes the Best method to only deprotect the carboxyl group of the compound shown below?

A. HBr (aq)

B.H2 + Pd/Carbon

C.CF3CO2H

D.NH3

E. piperidine

QUESTION 5


Which one answer Best describes the N-terminal amino acid in the structure below?

QUESTION 6


A. Pro

B.Met

C.Asn

D.Arg

E. Asp

Which one answer Best describes the C-terminal amino acid in the structure below?

A. Pro

B.Asp

QUESTION 7



C.Arg

D.Met

E. Asn

Which one answer is NOT True about the use of DCC in peptide synthesis? A. DCC is used to protect the carboxyl group of the Cterminal end of the peptide

B.DCC is a coupling agent

C.DCC can be used to add an amino acid to the Cterminal end of a peptide

D.DCC makes the carboxyl group of the amino acid more reactive

E. DCC accelerates the rate of peptide bond formation

QUESTION 8

Which one answer is NOT True about disulfide bridges ? A. Disulfide bonds are a covalent bond between two sulfur atoms

B.Disulfide bridges are covalent bonds that stabilize the protein structure

C.Disulfide bridges contribute to the overall shape of a protein

D.Disulfide bonds result from the reduction of two thiol groups

E. Disulfide bridges can be made between two Cys residues

QUESTION 9


Which one answer is NOT True about oxytocin (shown below)?

QUESTION 10


A.Oxytocin is linked to "trustinducing" behaviors

B.Gly is the Nterminal amino acid

C.Oxytocin is a nonapeptide

D.Oxytocin has a disulfide bond

E. There is no Phe in the primary structure

Preview Test: Quiz15_ProteinSequencing_Chem332

Test InformationDescription Chem 332 Quiz#15-ProteinSequencing - Part of Exam 3.


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Which of the compounds below is a reagent used to identify the N-terminal amino acid?Hint: It is listed as PITC in your notes. ~ Dr. K.

A. Compound A

B. Compound B





C.Compound C

D.Compound D

E. Compound E

Select the one statement that is most True about the peptide below.

A. Edman degradation produces the PTH derivative of Alanine

B. Complete hydrolysis produces three tyrosine residues.

C.Complete hydrolysis will produce only three different AAs that will react with ninhydrin

D.Digestion with Carboxypeptidase A will produce Glycine

E. Complete hydrolysis produces three proline residues

QUESTION 2

Select the one statement that is most True about the peptide below.

QUESTION 3



A. Complete hydrolysis produces three proline residues

B. Complete hydrolysis produces three tyrosine residues.

C.Digestion with Carboxypeptidase A will produce Glycine

D.Edman degradation produces the PTH derivative of Alanine

E. Complete hydrolysis will produce only three different AAs that will react with ninhydrin

Select the Answer that Best completes the missing terms in the following statement:_______ between a series of amino acids often contribute to the formation of (an) _______, which is part of the overall 3D shape in the _______

of the protein or peptide. Read this carefully. ~ Dr. K.A. Hydrogen bonding ... disulfide bridges ... secondary structure

B. Hydrogen bonding ... α-helix ... tertiary structure

C.London dispersion forces ... β−pleated sheets ... primary structure

D.Hydrogen bonding ... tertiary subunits ... quaternary structure

E. Electrostatic interactions ... β-pleated sheets ... primary sequence

QUESTION 4

The purpose of treating a protein with DTT is to ....A. cleave an amino acid sequence on the Nterminal side of Met

B. separate amino acids in an ion exchange column

C.break disulfide bridges

D.denature by destroying any nonbonding interactions

hydrolyse peptide bonds

QUESTION 5



E.

The purpose of treating a protein with ammonium sulfate is to ....A. separate amino acids in an ion exchange column

B. denature by destroying any nonbonding interactions

C.cleave an amino acid sequence on the Nterminal side of Met

D.break disulfide bridges

E. hydrolyze peptide bonds

QUESTION 6

Which one most likely CANNOT be used to determine the Nterminal amino acid in a peptide?A. Leucineaminopeptidase

B.Chymotrypsin

C.Dansyl chloride

D.Edman's Reagent

E. Sanger's Reagent

QUESTION 7


Which one is NOT an endopeptidase?A. Chymotrypsin

B.Pepsin

C.Carboxypeptidase B

D.Trypsin

E. Asp-N-protease

QUESTION 8


Which will elute first from an ion exchange column packed with anionic sulfonated polystyrene using pH=6 buffer solution?Amino acids with basic side chains

QUESTION 9


A.

B.Amino acids with acidic side chains

C.Amino acids with nonpolar side chains

D.Amino acids with polar side chains

E. Amino acids with polar neutral side chains

What are these three compounds?

A. 1) Ninhydrin 2) PTH of alanine 3) Sanger's Reagent

B.1) Ninhydrin 2) PTH of alanine 3) Dansyl fluoride

C.1) PITC 2) PTH of glycine 3) Sanger's Reagent

D.1) Ninhydrin 2) PTH of glycine 3) Sanger's Reagent

E. 1) Trypsin 2) Ninhydrin 3) Dansyl fluoride

QUESTION 10


combined

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compound bc

compound cd

compound equestion

compound ewhich

ozonolysis conditions

ozonolysis reaction

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