Organic Chem. 2 Final

Which of the following is an example of a conjugated dienes?

Which of the following dienes is most stable?

Which of the following dienes cannot be used as the diene component in Diels Alder Reaction?

Which of the following is expected to be aromatic?

What is a correct description of benzene?

The molecule is aromatic.

The CCC bond angles are all 120^o and each carbon is sp² .

The molecular is planar.

Which is required for aromaticity?

The structure must be planar.

The pi network must contain 4n+2 pi electrons, where n is a whole number.

Each atom in the ring must have an unhybridized p orbital.

What reagents are typically required to accomplish allylic bromination of an alkene?

NBS/CH₂Cl₂

Which of the following are only meta directing strongly deactivating group(s)?

-NO2

Which of the following is the electrophile that attacks the aromatic ring during nitration?

NO₂⁺

Which of the following functional group represents the benzyl group?

C₆H₅CH₂ –

Which of the following reagent(s) used for alkylation process of benzene?

CH₃Cl/AlCl₃      

Which of the following statements regarding the Diels–Alder reaction is true?

The diene must be s-cis and the major product is the endo product.

What is the product of the following reaction?

Predict the major product of the following reaction: 

No reaction

Identify which of the following are aromatic:

Which of the following structures is antiaromatic? 

Which of the following is the best choice of reagents to affect the electrophilic iodination of an aromatic ring?

I₂, CuCl₂

When considering electrophilic aromatic substitution reactions electron donating substituents are described as:

ortho/para directing and activating

Predict the major product of the following reaction: 

What reagents would be needed for the following reaction:

H₂/Pd

Predict the major product of the following reaction:

What reagents would be needed for the following reaction:

AlCl₃

What reagents would be needed for the following reaction:

CuCl/AlCl₃

Identify the following group as an activator or deactivator and as an o,p-director or m-director:

activator o,p-director

Rank the following aromatic compounds in the expected order of their reactivity toward Friedel–Crafts alkylation.

A. Bromobenzene

B. Toluene

C. Phenol

D. p-Bromotoluene

Phenol > Toluene > p-Bromotoluene > Bromobenzene

Which of the following will undergo rearrangement upon heating?

1.) 2-butenyl phenyl ether

2.) 1-propenyl 2-propenyl ether

3.) 2-pentenyl phenyl ether

4.) All of the above

All of the above.

2-butenyl phenyl ether

1-propenyl 2-propenyl ether

2-pentenyl phenyl ether

Of the types of reactions that characterize carbonyl groups, how is the following reaction classified?

α substitution

If the following substance were treated with HCN followed by aqueous acid and heat, which of the following would be produced? Atoms other than carbon and hydrogen are labeled.

Consider the following species. Atoms other than carbon and hydrogen are labeled. Which of the following would be produced upon treatment with I2?

Consider the following structure. Atoms other than carbon and hydrogen are labeled.

No reaction.

What are characteristics of a carbonyl group?

Sp2 hybridized carbon atom.

Planar geometry about the carbonyl bond.

Carbonyl carbon atom is electrophilic.

Carbonyl oxygen atom is nucleophilic.

Classify the following alcohol. Atoms other than carbon and hydrogen are labeled.

Tertiary.

Which of the following reagents could be used to convert 3-cyclopentyl-2-methylpropanal to the following substance?

CrO3

What product is formed when the following substance is treated with CrO3 under appropriate conditions?

Treatment of the following compound with Dess-Martin periodinane in CH2Cl2 would produce which of the following compounds?

Which types of compound is a negative charge on the acyl group not stabilized to function as a leaving group in a nucleophilic substitution reactions?

Acid chloride
Acid anhydride
Ester

The following substance is heated in the presence of aqueous NaOH. Atoms other than carbon and hydrogen are labeled. The product of the reaction is:

What is the product formed upon treatment of the following substance of the following substance with hydrogen peroxide at room temperature, followed by treatment with a peroxyacid? Atoms other than carbon and hydrogen are labeled.

What is the correct name for the following structure?

5-oxohexanoic acid

What is the order of increasing acidity for the following compounds? (least to most)

III, II, I, IV

The purpose of the acid catalyst in the hydrolysis of an amide is:

To enhance the electrophilicity of the amide carbonyl carbon.

Name three acyl derivatives of carboxylic acid.

Ester
Amide
Acid chloride

In order to produce a carboxylic acid as a product of the Grignard reaction, the Grignard reagent reacts with:

CO2

Which of the following will take place via nucleophilic acyl substitution?

Ester producing an amide.

In order to produce a carboxylic acid as a product of the Grignard reaction, the Grignard reagent reacts with:

CO2

The following reaction would be classified as which type of nucleophilic acyl substitution?

Grignard reaction

What is the product when the following substance reacts with trimethylamine ((CH3)3N)? Atoms other than carbon and hydrogen are labeled.

No reaction.

What reactant could produce the following substance upon treatment with CrO3 under acidic conditions? Atoms other than carbon and hydrogen are labeled.

2, 2-dimethylbutanal
2, 2-dimethyl-1-butanol

What is the name of the product when the following substance reacts with NaCH3COO? Atoms other than carbon and hydrogen are labeled.

Acetic 4-methylbutanoic anhydride

Which are examples of acyl derivatives if carboxylic acid?

Amide
Ester
Acid chloride

The following reaction could be classified as which type of nucleophilic acyl substitution?

Reduction

Which takes place via nucleophilic acyl substitution?

Ester producing an amide.

Consider the following molecular model. Atoms other than carbon and hydrogen are labeled. Which of the following reactants could be used to produce this compound.

2-choloropropanoic acid and ethanol.

What are common features in carboxylic acids and nitriles?

Carbon atom with three bonds to an electronegative atom.

Presence of π bonds.

Can act as electrophiles.

Consider the structure given below which might be found in protein. What is applicable to this structure?

Contains three monomers.

Contains amide bonds.

Contains three types of monomers.

The following reaction could be classified as which type of nucleophilic acyl substitution?

Hydrolysis.

What best describes nucleophilic acyl substitution?

Nucleophile replaces a group adjacent to the carbon of carbonyl.

The following reaction could be classified as which type of nucleophilic acyl substitution?

Alcoholysis.

In carbonyl condensation reactions, the carbonyl group acts as:

Both an electrophile and a nucleophile.

The product of an aldol condensation reaction is generally favored if

an aldehyde has no alpha substituents.

Which of the following does not characterize carbonyl condensation reactions?

rare in biological systems

Compared to pentylamine, pentane is:

Less basic.

What will produce a five-membered ring via a Dieckmann cyclization?

1,6-diester

Classify the following amine. Atoms other than carbon and hydrogen are labeled.

Tertiary.

Can can result in cyclization:

Aldol condensation
Claisen condensation
Robinson annulation

What is the structure of the enamine produced in the reaction of cyclohexanone with piperidine?

What reactions are the ester analogs of an aldol condensation?

Claisen condensation
Dieckman cyclization

For which of the following will the aldol reaction go the furthest toward completion?

Which of the hydrogen atoms indicated by a number is the most acidic in the structure below?

1

What characterizes carbonyl condensation reactions?

Forms new C-to-C bonds
Enolate ion can act as a nucleophile
α hydrogen required for an aldol condensation

Using the acetoacetic ester synthesis, to produce 5-methyl-2-heptanone, the alkyl halide that should be used is:

1-bromo-2-methyl butane

Which Tautomer form is more stable?

The enol form is generally more stable.

What is a method of preparing amines that can be used to prepare primary, secondary, and tertiary amines?

Reduction amination of a ketone.

The alkyl halide that should be used to produce octanoic acid via the malonic ester synthesis is:

1-bromohexane

Which of the following when reacted with butanal would be the most likely to produce a single aldol product?

Consider the following molecule model. Atoms other than carbon and hydrogen are labeled. Bromination of the substance represented would be dependent on the concentration of:

Ketone and Acid

Experimentally to produce 2-ethylpentanal from pentanal, how should the reaction conditions be adjusted to ensure the alpha substitution product rather than the aldol product result or a mixture of the two products?

Add a full equivalent of a strong base and add the alkylating agent after the addition of the base.

What is an example of a Michael donor?

1-nitropentane

This generalized structure represents:

One of the resonance forms of the acid catalyzed intermediate between a keto and enol tautomer.

The product of an aldol condensation reaction is generally favored if:

An aldehyde has no α substituents.

Which of the following will not undergo an aldol condensation reaction?

2, 2-dimethylbutanal

Which of the following is not classified as a heterocycle?

What method of preparing amines results in an amine with one less carbon atom than starting the material?

Hofman rearrangement of an amide.