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Preview Test: Quiz1_Ozonolysis_Chem332

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

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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 2

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 3

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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

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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
E. None of these compounds

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

A. Compound A
B. Compound B
C. Compound C
D. Compound D
E. Compound E

Question 6

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

A. Compound A
B. Compound B
C. Compound C
D. Compound D
E. Compound E

Question 7

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Which molozonide will form formaldehde under ozonolysis conditions ?

A. Compound A
B. Compound B
C. Compound C
D. Compound D
E. Compound E

Question 8
Which ozonide will form formaldehde under ozonolysis conditions ?

A. Compound A
B. Compound B
C. Compound C
D. Compound D
E. Compound E

Question 9

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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

Question 10

Which ONE is NOT used as a Reagent in the workup conditions of an ozonolysis reaction that produces an
aldehyde.
A. Acetic Acid
B. Zinc metal
C. Vinegar
D. DMSO
E. CH3-S-CH3

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Quizzes for Exam 1

Preview Test: Quiz2_Conjugation_Chem332

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Preview Test: Quiz2_Conjugation_Chem332

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

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Question 1

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Which structure is NOT conjugated ?

A. Compound A
B.

Compound B

C. Compound C
D. Compound D
E.

Compound E

Question 2
Which Structures are conformers?

A. Structure
B.

A and Structure D

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

Question 3

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

A. Structure
B.

Structure C

C. Structure

D. Structure

E.

Structure E

Question 4
Which conjugated diene is currently in an s-cis conformation ?

A. Compound
B.

Compound B

C. Compound

D. Compound

E. None of these compounds

Question 5
Which conjugated diene is currently in an s-trans conformation ?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

Compound E

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

A. Structure
B.

B and Structure E

Structure A and Structure D

C. Structure C and Structure D

D. Structure
E.

B and Structure D

Structure B and Structure C

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Question 7
Which ONE statement is True about the addition reaction shown below?

A. The
B.

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

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.

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

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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.

Question 9
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.

Question 10
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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Quizzes for Exam 1

Preview Test: Quiz3_DielsAlder_Chem332

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Preview Test: Quiz3_DielsAlder_Chem332

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

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

A.

B.

C.

D.

Question 2
Which of the compounds will react as a diene in a Diels-Alder reaction?

A. Compound
B.

Compound B

B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

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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

Question 4
Identify the diene and dienophile which would give the Diels Alder product shown.

A. Reagents
B.

Reagents B

C. Reagents

D. Reagents

E.

None of these.

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

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

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Identify the diene used in the reaction shown above.

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 7
What is the product of the reaction shown below?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 8

Which conjugated diene would react the fastest with maleic anhydride?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

Compound E

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

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

Compound E

Question 10
Which structure (A-E) represents the product of this reaction?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

Compound E

E.

Compound E

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Preview Test: Quiz4_Alcohols_Chem332

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Preview Test: Quiz4_Alcohols_Chem332

Description

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

Instructions
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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)
2)
3)
4)

LiAlH4, ether
H3O+
MeMgBr, ether
H3O+

Question 2
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

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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.

Question 4

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

A. Reactants
B.

Reactants B

C. Reactants

D. Reactants

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Give the major organic product for the reaction below.

A. Compound
B.

Compound B

C. Compound

D. Compound

Question 6
Give the major organic product for the reaction below.

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

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Give the major organic product for the reaction below.

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 8
Give the major organic product from the reaction below.

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

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

A. None
B.

of these Reagent Sets.

1) TMS-Cl, Et3N
2) MeMgBr, ether
3) H3O+

C. PCC,

CH2Cl2

D. 1)

NaBH4, ethanol
2) H3O+

E.

1) LiAlH4, ether
2) H3O+

Question 10
Choose the best set of reagents for carrying out the chemical conversion (below).

A. 1)

NaBH4, ethanol

1) NaBH4, ethanol
2) H3O+
B.

1) TMS-Cl, Et3N
2) MeMgBr, ether
3) H3O+

C. None
D. PCC,
E.

of these Reagent Sets.

CH2Cl2

1) PBr3
2) NaOH

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Preview Test: Quiz5_Aldehydes and Ketones_Chem332

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Preview Test: Quiz5_Aldehydes and Ketones_Chem332

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Chem 332 Quiz#5 (part of Exam#1)

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
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Question 1

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What functional group results from the reaction shown below?

A. aldehyde
B.

carboxylic acid

C. alcohol
D. conjugated
E.

diene

ketone

Question 2
What is the product of the reaction shown below?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 3

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

A. 1)
B.

NaBH4, ethanol 2) H3O+

NaCN, DMSO

C. NaOH,
D. 1)
E.

methanol, heat

CH2=P(Ph)3 2) H3O+

PCC

Question 4
Which of the compounds below is an acetal?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 5
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

Question 6

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What is the product of the reaction below?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Conpounds

Question 7
What are the products of the reaction shown below?

A. cyclohexanone
B.

and ethanol

cis-1,2-cyclohexanediol and ethanol

C. trans-1,2-cyclohexanediol
D. cyclohexanone
E.

and ethanol

and ethanal

cis-1,2-cyclohexanediol and ethanal

Question 8
What is the product of the reaction shown below?

A. 4-methyl-1-pentene
B.

1-pentene

C. 2-methyl-1-hexene
D. 2-methyl-1-pentene

E.

2-methyl-2-propyloxirane

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Identify the missing reagent for the reaction shown below.

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 10
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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Quizzes for Exam 2

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Preview Test: Quiz6_Carboxylic Acids_Chem332

Description

Chem 332 Quiz#6 (part of Exam#2)

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]

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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

Question 2
Which reagent CANNOT ever be used on an aldehyde to produce a carboxylic acid?
A. the
B.

oxygen in air + water

Ag2O + base

C. hydrogen
D. The
E.

peroxide

Silver Mirror Test

LAH

Question 3
Name the compounds below.

A. 3-propylpentanoic

acid
4-hydroxy-3-methylbutanoic acid
2-bromo-4-ethylbenzenecarboxylic acid

B.

3-ethylhexanoic acid
4-hydroxy-3-methylbutanoic acid
4-ethylbenzenecarboxylic acid

C. 3-propylpentanoic

acid
3-(hydroxymethyl)butanoic acid
2-bromo-4-ethylbenzenecarboxylic acid

D. 3-ethylhexanoic

acid
4-hydroxy-3-methylbutanoic acid
2-bromo-meta-ethylbenzenecarboxylic acid

E.

3-ethylhexanoic acid
4-hydroxy-3-methylbutanoic acid
2-bromo-4-ethylbenzenecarboxylic acid

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

A. A
B.

C. C
D. D
E.

None of these structures

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

A. Structure A
B.

Structure B

C. Structure

D. Structure

E.

None of the Structures

Question 6
Identify the lactone resulting from the INTRAmolecular Fischer-Esterification of the compound shown below.

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A. Structure
B.

Structure B

C. Structure

D. Structure

E.

None of the Structures

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

A. reduce with H 2
B.

hydrolyze with aqueous acid (H3O+) and heat.

C. reduce with LiAlH 4

D.

oxidize with Ag+

E.

add a Grignard reagent

Question 8
Choose the BEST reagent(s) for carrying out the reaction below.

A. O

3, then Zn and HOAc

B.

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

C. KMnO

4 under basic conditions with heat

D. 1. NaCN 2. H
E.

2SO4, H2O, heat

Tollens Reagent

Question 9
Which carboxylic acid has the highest boiling point?
A. glycolic
B.

acid

butanoic acid

C. 2-hydroxypropanoic

acid

D. propionic
E.

acid

-hydroxybutyric acid

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What are the names of these carboxylic acids?

A. glycolic

acid
lactic acid
-methylbutyric acid

B.

1-hydroxypropionic acid
glycolic acid
-methylbutanoic acid

C. 2-hydroxypropanoic

salicylic acid
-methylbutyric acid

acid

D. glycolic

acid
2-hydroxyethanoic acid
-methylbutyric acid

E.

glycolic acid
lactic acid
1-methylbutyric acid

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Quizzes for Exam 2

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Description

Chem 332 Quiz#7 (part of Exam#2)

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

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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
B.

> Hb > Hc Hd

Ha > Hb Hc > Hd

C. Hb

> Ha Hd > Hc

D. Ha

> Hb Hd > Hc

E.

Ha Hb > Hc Hd

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

A. III
B.

> II > I

II > III > I

C. II

> I > III

D. I

> II > III

E.

I > III > II

Question 3
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

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

A. four
B.

(4)

None

C. six

(6)

D. three
E.

(3)

two (2)

Question 5
Alkylation with methyl iodide of the kinetic enolate of the compund shown below produces which product?

A. Compound
B.

Compound B

C. Compound

D. Compound

Question 6
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

Question 7
What is the product of the reaction below?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of the Compounds

Question 8

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

A. III
B.

> II > I

II > III > I

C. III
D. I

> I > II

> II > III

Question 9
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
B.

Compound B

C. Compound

D. Compound

Question 10
Identify the major organic product of the above reaction.

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of the Compounds

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Quizzes for Exam 2

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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
Timed Test This Test has the time limit of 2 hour. You are notified when time expires, and you may continue or submit.
Warnings appear when half the time, 5 minutes, 1 minute, and 30 seconds remain.[The timer does not appear when previewing this Test]
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Question 1

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Predict the product from the reaction sequence (below).

A. Compound
B.

Compound B

C. Compound

D. Compound

Question 2
What gas evolves at the end of the acetoacetic ester sequence?
A. H

B.

SO2

C. carbon

dioxide

D. oxygen
E.

H2O vapor

Question 3
Which of the following is used in the enolate chemistry shown below?

A. Compound
B.

Compound B

C. Compound

D. Compound

Question 4

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Name the compounds.

A. malaeic
B.

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

C. ethyl

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

D. diethyl
E.

anhydride, enol of acetone, LDA, Sodium acetate & acetoacetic ester

malonate, enol of acetone, LSD, Sodium acetate & acetoacetic ester

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

Question 5
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.

Question 6
Give the major organic product of the reaction (below).

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 7

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

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 8
Give the major organic product of the reaction (below) done at RT (room temperature).

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

Question 9
In the acetoacetic acid synthesis (shown below), which one of the following electrophiles is used?

A. Compound

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Componds.

0.5 points

Question 10

Save Answer

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

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds

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Course Content

Quizzes for Exam 2

Preview Test: Quiz9_AldolClaisen_Chem332

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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
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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Attempts
Force
Once started, this Test must be completed in one sitting.
Completion
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Question 1

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Consider the reaction below and select the the best answer:

A. B
B.

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

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
E.

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

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

Question 2
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

0.5 points

Question 3

Save Answer

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
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

Question 4

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Which is the product of this intramolecular aldol condensation reaction?

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

Question 5

0.5 points

Question 5

Save Answer

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

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

Question 6

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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

Question 7
Which of the following is the Claisen self-condensation product of ethyl propanoate, CH3CH2CO2Et ?

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A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

0.5 points

Question 8

Save Answer

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, CH

3CO2Et

B.

diethyl oxalate, EtO2CCO2Et

C. Carbonic

Acid, HOCO2H

D. ethyl formate, HCO

E.

2Et

diethyl carbonate, (EtO)2C=O

Question 9

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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

Question 10
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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Course Content

Quizzes for Exam 2

Preview Test: Quiz10_MichaelEnamineRobinson_Chem332

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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
Timed Test This Test has the time limit of 2 hour. You are notified when time expires, and you may continue or submit.
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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Attempts
Force
Once started, this Test must be completed in one sitting.
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Question 1

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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

0.5 points

Question 2

Save Answer

Which one of the following reagents adds a methyl group by conjugate (1,4-addition) addition to an ,-unsaturated
ketone or aldehyde?
A. (CH

3)2CuLi

A. (CH

3)2CuLi

B.

CH3MgBr

C. LAH
D. CH3Li
E.

Hg(OAc)2

0.5 points

Question 3

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Heating a mixture of 1,3-diphenylacetone and acrolein with a weak base gives a product, C18H16O, in 53% yield. The
mechanism for product formation is a Michael addition followed by an intramolecular aldol condensation. Which of the
above 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
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

0.5 points

Question 4
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

Save Answer

Compound A
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

Question 5

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The Stork Enamine reaction is a Michael addition on an enone.

Predict the product of the reaction sequence (shown below).

A. Compound
B.

Compound B

C. Compound

D. Compound

E.

None of these Compounds.

Question 6
To make this compound (below), you need:
Select the BEST answer available

A. Gilman
B.

Reagent and an enone

An enamine and a ketone

C. Gilman

Reagent and an enamine

D. MethylGrignard
E.

and an enone

Gilman Reagent and a ketone

Question 7

What just happened here ??

A. Conjugate
B.

Direct (1,2-) Addition + Aldol

C. Conjugate
D. Direct
E.

(Michael) Addition + Robinson Annulation

(Michael) Addition + Aldol

(1,2-) Addition + Claisen

Conjugate (Michael) Addition + Dieckmann

Question 8

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

A. Gilman
B.

Reagent + Aldehyde

Enamine + -bromoester

C. Enamine
D. Cuprate
E.

+ Enone
+ Ester

Enolate + enone

Question 9
How can you make a 1,5-dicarbonyl compound?
A. Enamine
B.

+ Alkylhalide

Cuprate + Ester

C. Gilman

Reagent + Aldehyde

D. Enolate

+ enone

E.

Enamine + -bromoester

Question 10
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 Information
Description
Instructions
Timed Test

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Attempts

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

This test has a time limit of 2 hours.This test will save and submit automatically when the time expires.
Warnings appear when half the time, 5 minutes, 1 minute, and 30 secondsremain.[The timer does not appear
when previewing this test]
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QUE S TION 1

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Select the name for this compound below.

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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

QUE S TION 2

Whichmusthaveahigherboilingpoint(bp)thanN,Ndimethyl2
hexanamine?
(Select the BEST answer based on your knowledge of the relationship
0.5 points
between 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
E. all

Save Answer

amine with lower mol. weight (fewer carbons)

amines with at least six total carbons

QUE S TION 3

Thecompoundbelowisclassifiedasa(n):
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A. secondaryamine.
B. amide.
C. arylamine
D. tertiaryamine.
E. primaryamine.

QUE S TION 4

Whatistheproductofthereactionsequenceshownbelow?
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A. Compound

B. Compound

C. Compound

D. Compound

E. None

of these Compounds

QUE S TION 5

What is the product of the reaction sequence shown below ?

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A. Compound

B. Compound

C. Compound

D. Compound

E. None

of these Compounds

QUE S TION 6

What is the product of the reaction shown below ?

A. Compound

B. Compound

C. Compound

D. Compound

E. None

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of these Compounds

QUE S TION 7

What is the product of the reaction sequence shown below ?

A. Compound

B. Compound

C. Compound

D. Compound

E. None

of these Compounds

QUE S TION 8

What is the product of the reaction sequence shown below ?

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A. Compound

B. Compound

C. Compound

D. Compound

E. None

of these Compounds

QUE S TION 9

The structure of heroin is shown below.

Which ONE phrase is NOT true about this compound?
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A. tertiary

amine

B. opioid
C. can

be derived from morphine

D. major

component of poppy pods

E. highly

addictive / habit forming

QUE S TION 10

Which is NOT True about N-ethylaniline ?

A. chiral at very low temperatures
B.

sp3 hybridized nitrogen

C. cannot

form hydrogen bonds

D. secondary
E. arylamine

amine

Preview Test: Quiz12_AmineRxns_Chem332

Test Information
Description
Instructions
Timed Test

Multiple
Attempts

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

This test has a time limit of 2 hours.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]
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QUE S TION 1

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What is the product of the reaction sequence shown below?

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A. Compound A
B. Compound B
C. Compound C
D. Compound D
QUE S TION 2

Whatisthemajorproductofthereactionsequencebelow?
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A. Compound A
B. Compound B
C. Compound C

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D. Compound D
QUE S TION 3

Whichistrueaboutthebasicityofthenitrogenlonepairsinthecompoundbelow?
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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
QUE S TION 4

WhichONEanswermostaccuratelydescribestheStructures(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
QUE S TION 5

WhichONEanswermostaccuratelydescribestheStructures(below)?

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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
QUE S TION 6

WhichONEanswermostaccuratelyranksthebasicityofsubtitutedanilines?
(Mostbasiccompoundontheleft/Leastbasiccompoundontheright)
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
QUE S TION 7

WhichONEanswermostaccuratelyliststhereactionstepsforthistransformation?

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

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

C. 1)hydrogenation 2)diazotization 3)Sandmeyer

D. 1)hydrogenation 2)nitrosation 3)Sandmeyer
E. 1)Sn+HCl 2)nitrosation 3)copper(I)oxide
QUE S TION 8

WhichONEanswermostaccuratelyliststhereactionstepsforthistransformation?

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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
QUE S TION 9

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.

A. Compound A
B. Compound B
C. Compound C
D. Compound D
E. None of these Compounds
QUE S TION 10

What is the product of the reaction sequence shown below ?

A. Compound A
B. Compound B
C. Compound C
D. Compound D
E. None of these Compounds

Preview Test: Quiz13_AminoAcids_Chem332

Test Information
Description Chem 332 Quiz#13-AminoAcids - Part of Exam 3.
Instructions
Timed 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 30
seconds remain.[The timer does not appear when previewing this test]
Multiple This test allows multiple attempts.
Attempts

QUESTION 1

Question Completion
Status:
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Humansareabletosynthesizeonly10ofthe20commonaminoacidsnecessaryforproteinsynthesis.Theremaining10arecalled__________aminoacidssincet
deficient

A.

B. nonessential
C. dietary
D. complex
E. essential
QUESTION 2

QUESTION 2
GiventhepKadatabelow,selecttheonestatementthatismosttrue.

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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 3
GiventhepKadatabelow,selecttheonestatementthatismosttrue.

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

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
QUESTION 4
Whichofthecompoundsbelowisthezwitterionformofalanine?

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A. Compound A
B. Compound B
C. Compound C
D. Compound D
QUESTION 5
a

GlutamicAcid(structureshownbelowwithpK values),hasapIof?

A. 6.96
B. 7.0
C. 5.37
D. 3.22
E. 5.93
QUESTION 6
TheFischerprojectionshownbelowdenotesa______aminoacidwhichhasthe_____configuration.

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A. L, S
B. L, R
C. D, R
D. D, S
QUESTION 7
Which amino acid CANNOT be formed from this synthetic method?
0.5 points
A. Leucine
Glycine

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B.
C. Proline
D. Valine
E. Alanine
QUESTION 8
Which amino acid CANNOT be formed from this synthetic method?
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A. Valine
B. Leucine
C. Phenylalanine
D. Glycine
E. Alanine
QUESTION 9
Whichreactantisneededforthesynthesisofalanineusingreductiveamination?
Selecttheonebestanswer.
BINAP catalyst

A.

B.

acetaldehyde

C. enamidoacid

D. pyruvicacid
E. Nacetylatedenamine
QUESTION 10
WhichreactantisneededforthesynthesisofalanineusingtheStreckersynthesis?
Selecttheonebestanswer.
BINAPcatalyst

A.

B. Nacetylatedenamine
C. acetaldehyde
D. pyruvicacid
E. enamido acid

Preview Test: Quiz14_Peptides_Chem332

Test Information
Description Chem 332 Quiz#14-Peptides - Part of Exam 3.
Instructions
Timed Test

Multiple
Attempts

This test has a time limit of 2 hours.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]
This test allows multiple attempts.

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QUESTION 1

Question Completion Status:

Whichoneansweristheabbreviatedformulaofthepeptideshownbelow?
Hint:Identifytheamidebonds,thenidentifyeachaminoacid.~Dr.K.

A. lysseraspala
B. serlysalaasp
C. aspalaserlys
D. aspseralalys

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E. aspalasertyr
QUESTION 2
Which one answer Best describes the structure shown below?

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A. tBocPhePro
B. FmocPhePro
C. FmocProPhe
D. tBocProPhe
E. tBocAlaPro
QUESTION 3
Which one answer Best describes the structure shown below?

A. FmocLys
B. NacylFmocLys
C. NacyltBocArg
D. NacyltBocLys
NacylFmocArg

E.
QUESTION 4
Which one answer Best describes the product that forms when the compound below is treated with ammonia?

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A. tBocGlu
B. FmocLys
C. FmocArg
D. tBocLys
E. FmocGlu
QUESTION 5
Which one answer describes the Best method to only

deprotect the carboxyl group of the compound shown below?

0.5 points

A. HBr(aq)
B. H2+Pd/Carbon
C. CF3CO2H
D. NH3
E. piperidine
QUESTION 6
Which one answer Best describes the N-terminal amino acid in the structure below?

Save Answer

0.5 points

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A. Pro
B. Met
C. Asn
D. Arg
E. Asp
QUESTION 7
Which one answer Best describes the C-terminal amino acid in the structure below?

A. Pro
B. Asp

C. Arg
D. Met
E. Asn
QUESTION 8
Which one answer is NOT True about the use of DCC in peptide synthesis?
A. DCCisusedtoprotectthecarboxylgroupoftheCterminalendofthepeptide

B. DCCisacouplingagent

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C. DCCcanbeusedtoaddanaminoacidtotheCterminalendofapeptide
D. DCCmakesthecarboxylgroupoftheaminoacidmorereactive
E. DCCacceleratestherateofpeptidebondformation
QUESTION 9
Which one answer is NOT True about disulfide bridges ?
A. Disulfidebondsareacovalentbondbetweentwosulfuratoms

B. Disulfidebridgesarecovalentbondsthatstabilizetheproteinstructure
C. Disulfidebridgescontributetotheoverallshapeofaprotein
D. Disulfidebondsresultfromthereductionoftwothiolgroups
E. DisulfidebridgescanbemadebetweentwoCysresidues
QUESTION 10
Which one answer is NOT True about oxytocin (shown below)?

A. Oxytocinislinkedto"trustinducing"behaviors
B. GlyistheNterminalaminoacid
C. Oxytocinisanonapeptide
D. Oxytocinhasadisulfidebond
E. ThereisnoPheintheprimarystructure

Preview Test: Quiz15_ProteinSequencing_Chem332

Test Information
Description Chem 332 Quiz#15-ProteinSequencing - Part of Exam 3.
Instructions
Timed Test

Multiple
Attempts

This test has a time limit of 2 hours.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]
This test allows multiple attempts.

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QUESTION 1

Question Completion Status:

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

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C. Compound C
D. Compound D
E. Compound E
QUESTION 2
Select the one statement that is most True about the peptide below.

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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 3
Select the one statement that is most True about the peptide below.

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

QUESTION 4

SelecttheAnswerthatBestcompletesthemissingtermsinthefollowingstatement:
_______betweenaseriesofaminoacidsoftencontributetotheformationof(an)_______,whichispartoftheoverall3
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oftheproteinorpeptide.Readthiscarefully.~Dr.K.
A. Hydrogenbonding...disulfidebridges...secondarystructure
B. Hydrogen bonding ... -helix ... tertiary structure
C. London dispersion forces ... pleated sheets ... primary structure
D. Hydrogen bonding ... tertiary subunits ... quaternary structure
E. Electrostatic interactions ... -pleated sheets ... primary sequence
QUESTION 5
ThepurposeoftreatingaproteinwithDTTisto....
A. cleaveanaminoacidsequenceontheNterminalsideofMet

B. separateaminoacidsinanionexchangecolumn
C. breakdisulfidebridges
D. denature by destroying any nonbonding interactions
hydrolysepeptidebonds

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E.
QUESTION 6
Thepurposeoftreatingaproteinwithammoniumsulfateisto....
A. separateaminoacidsinanionexchangecolumn

B. denature by destroying any nonbonding interactions

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C. cleaveanaminoacidsequenceontheNterminalsideofMet
D. breakdisulfidebridges
E. hydrolyzepeptidebonds
QUESTION 7
WhichonemostlikelyCANNOTbeusedtodeterminetheNterminalaminoacidinapeptide?
A. Leucineaminopeptidase

B. Chymotrypsin
C. Dansylchloride
D. Edman'sReagent
E. Sanger's Reagent
QUESTION 8
WhichoneisNOTanendopeptidase?
A. Chymotrypsin

B. Pepsin
C. CarboxypeptidaseB
D. Trypsin
E. Asp-N-protease
QUESTION 9

WhichwillelutefirstfromanionexchangecolumnpackedwithanionicsulfonatedpolystyreneusingpH=6buffersolution?
Aminoacidswithbasicsidechains

A.

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B. Aminoacidswithacidicsidechains
C. Aminoacidswithnonpolarsidechains
D. Aminoacidswithpolarsidechains
E. Aminoacidswithpolarneutralsidechains
QUESTION 10
Whatarethesethreecompounds?

A. 1)Ninhydrin2)PTHofalanine3)Sanger'sReagent
B. 1)Ninhydrin2)PTHofalanine3)Dansylfluoride
C. 1)PITC2)PTHofglycine3)Sanger'sReagent
D. 1)Ninhydrin2)PTHofglycine3)Sanger'sReagent
E. 1)Trypsin2)Ninhydrin3)Dansylfluoride

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