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Example Questions
Example Question #6 : Reaction Types
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.
reduced . . . alkane
reduced . . . alcohol
oxidized . . . carboxylic acid
oxidized . . . amide
reduced . . . alkane
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 #1 : Carbonyls
What reagent(s) will successfully complete the synthesis reaction shown above?
Methyl-MgCl; hydronium ions
N-propyl-MgBr; hydronium ions
Ethyl-MgI; hydronium ions
Isopropyl-MgBr; hydronium ions
N-propyl-MgBr; hydronium ions
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 : Reduction Reactions
The reaction of a Grignard reagent with ethylene oxide (oxirane) followed by work-up with dilute acid gives which of the following products?
A tertiary alcohol
Ethanol
No alcohol
A primary alcohol
A secondary alcohol
A primary alcohol
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 : Reduction Reactions
Predict the major product of the given Grignard reaction.
II
I
IV
III
None of these
I
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 : Reduction Reactions
What is the product of the reaction shown?
I
IV
II
III
I
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
Determine the major product of the given intramolecular aldol reaction.
None of these
III
I
IV
II
II
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 #11 : Specific Reactions And Named Reactions
What is the final organic product of the reaction shown?
I
III
V
IV
II
I
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 #12 : Specific Reactions And Named Reactions
What is the product of this reaction?
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 : Carbonyl Reactions
What is the final organic product of the reaction shown?
I
V
III
IV
II
III
First step: esterification
Second step: reduction
Third step: neutralization
Fourth step: oxidation to aldehyde
Fifth step: alkene metathesis
Example Question #2 : Reaction Types
All of the following are characteristics of a Wittig reaction except __________.
it results in the exclusive formation of trans double bonds
it produces a trialkylphosphine oxide or triarylphosphine oxide as a by-product
it results in the formation of a carbon-carbon double bond
it proceeds through a phosphaoxetane intermediate
it involves the reaction of a phosphonium ylide with a carbonyl
it results in the exclusive formation of trans double bonds
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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