Organic Chemistry : Specific Reactions and Named Reactions

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #11 : Specific Reactions And Named Reactions

Acetaldehyde  undergoes a Wolf-Kishner reaction, which is the addition of hydrazine  with subsequent addition of a base and heat. In this reaction, the aldehyde is __________, resulting in a(n) __________ product.

Possible Answers:

oxidized . . . carboxylic acid

reduced . . . alkane

oxidized . . . amide

reduced . . . alcohol

Correct answer:

reduced . . . alkane

Explanation:

The correct answer is that the aldehyde is reduced to an alkane. In viewing the final product, we see that acetaldehyde would be reduced to ethane. The reaction of any aldehyde or ketone with hydrazine and the subsequent addition of base and heat will result in that aldehyde or ketone being reduced to an alkane, and is referred to as the Wolf-Kishner reaction. The Wolf-Kishner reagent is a commonly tested reducing agent.

Example Question #11 : Organic Chemistry

Grinard

What reagent(s) will successfully complete the synthesis reaction shown above?

Possible Answers:

N-propyl-MgBr; hydronium ions

Ethyl-MgI; hydronium ions

Methyl-MgCl; hydronium ions

Isopropyl-MgBr; hydronium ions

Correct answer:

N-propyl-MgBr; hydronium ions

Explanation:

This is an example of a Grignard reagent reaction. Because we are adding three carbons to our chain, the Grignard reagent we need must have three carbons on it. We can therefore rule out methyl grignard and ethyl grignard.

N-propyl is the straight-chained 3-carbon alkane, while isopropyl is branched. Looking at our final product, we can see the carbon chain we have added is straight-chained, and thus N-propyl Grignard is the best option. Because Grignard reagents are relatively basic, we must add an hydronium ion workup to protonate our alcohol.  

Example Question #1 : Help With Grignard Reactions

The reaction of a Grignard reagent with ethylene oxide (oxirane) followed by work-up with dilute acid gives which of the following products?

Possible Answers:

No alcohol

A tertiary alcohol

Ethanol

A primary alcohol

A secondary alcohol

Correct answer:

A primary alcohol

Explanation:

The reaction of a Grignard reagent with oxirane (a type of epoxide) in addition to the work-up with dilute acid will yield a primary alcohol solely because there is a work-up with dilute acid. This shows that there is an excess of hydrogen, which will yield to a primary alcohol versus a secondary or tertiary alcohol.

Example Question #2 : Help With Grignard Reactions

Screen shot 2015 07 19 at 10.47.03 am

Predict the major product of the given Grignard reaction.

Possible Answers:

III

IV

I

None of these

II

Correct answer:

I

Explanation:

Grignard reagents (often formed in-situ due to their highly non-specific reactivity) act as reducing agents by forming carbanions, which are strong bases and nucleophiles. Nitriles may react with Grignard reagents to form imines. The reaction proceeds in an analogous fashion to a standard nucleophilic carbonyl addition, converting the triple bond to a double bond by forming an intermediate in which nitrogen carries a negative charge. A protic solvent, such as ethanol, is then added to neutralize the intermediate. Thus, the correct answer is the only compound in which an imine is formed, which is found in compound I.

Example Question #3 : Help With Grignard Reactions

What is the product of the reaction shown?

Screen shot 2015 11 13 at 2.18.46 pm

Screen shot 2015 11 13 at 2.18.40 pm

Possible Answers:

IV

II

I

III

Correct answer:

I

Explanation:

Step 1 converts the carboxylic acid into an ester.

Step 2 adds two equivalents of Grignard reagent: one to turn the molecule into acetone, and a second one to turn it into tert-butoxide. There is no way to stop the reaction after the first addition of Grignard reagent.

Step 3 will neutralize the base, leaving only t-butyl alcohol (I).

Example Question #651 : Organic Chemistry

Screen shot 2015 07 07 at 8.30.46 pm

Determine the major product of the given intramolecular aldol reaction.

Screen shot 2015 07 07 at 8.30.53 pm

Possible Answers:

IV

I

II

None of these

III

Correct answer:

II

Explanation:

Keep in mind the following principles: Cyclization is favored when a five/six-member ring may be formed. Addition at an aldehyde is favored relative to the same reaction at a ketone. 

As a result, abstraction of a hydrogen bound to carbon 6 (an alpha-carbon) is favored since the resulting carbanion may attack the aldehyde (carbon 1) to form a six-member ring, resulting in compound II. Compound I results from abstracting a hydrogen from carbon 2, generating a carbanion which may then attack the ketone. Based on the latter of the above principles, this is a minor product.

Example Question #1 : Carbonyl Reactions

What is the final organic product of the reaction shown?

Screen shot 2015 11 13 at 2.54.29 pm

Screen shot 2015 11 13 at 2.54.56 pm

Possible Answers:

V

II

I

IV

III

Correct answer:

I

Explanation:

First step: Friedel-Crafts acylation of benzene

Second step: Formation of enolate

Third step: aldol addition (enolate attacks carbonyl carbon in benzaldehyde)

Fourth step: neutralization of anion and dehydration forming alkene

Example Question #1 : Carbonyl Reactions

Esterification

What is the product of this reaction?

Possible Answers:

3

2butanone

6

2

Ester

Correct answer:

Ester

Explanation:

This is a classic esterification reaction. Esterfication occurs when a carboxylic acid and an alcohol are reacted together. Only one answer choice is an ester. 

Example Question #1 : Help With Wittig Reactions

What is the final organic product of the reaction shown?

Screen shot 2015 11 14 at 11.07.54 am

Screen shot 2015 11 14 at 11.04.22 am

Possible Answers:

IV

V

III

I

II

Correct answer:

III

Explanation:

First step: esterification

Second step: reduction

Third step: neutralization

Fourth step: oxidation to aldehyde

Fifth step: alkene metathesis

Example Question #1 : Reactions With Ketones And Aldehydes

All of the following are characteristics of a Wittig reaction except __________.

Possible Answers:

it produces a trialkylphosphine oxide or triarylphosphine oxide as a by-product

it results in the formation of a carbon-carbon double bond

it involves the reaction of a phosphonium ylide with a carbonyl

it results in the exclusive formation of trans double bonds

it proceeds through a phosphaoxetane intermediate

Correct answer:

it results in the exclusive formation of trans double bonds

Explanation:

The Wittig reaction involves the reaction of a phosphonium ylide (generated by treating a phosphonium salt with a strong base) with a ketone or aldehyde.

The reaction proceeds through a phosphaoxetane (4-membered ring containing both phosphorus and oxygen) intermediate to generate a new compound containing a carbon-carbon double bond, plus a phosphine oxide byproduct. It does not form trans double bonds exclusively; sometimes, a mixture of cis and trans isomers are obtained, and sometimes the cis isomer is the predominant product. 

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