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Reactions of Carbonyl Compounds

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1. Complete the following reaction by drawing a structural formula for the product.
?
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
2. Draw a structural formula for the major organic anion formed when 2-ethylbenzaldehyde is reacted with Tollens' reagent.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• If no reaction occurs, draw the starting material.
3. Draw a structural formula for the product formed when cyclopentanone is reduced by hydrogen in the presence of a transition-metal catalyst.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
4. Complete the following reaction by drawing a structural formula for the product.
+ H2 ?

5. Give the name of the missing organic reactant in the following reaction.

? + 2 Ag(NH3)2+ + 3 OH- + 2 Ag + 4 NH3 + 2 H2O
6. Complete the following single-step reaction by writing the name of the reactant.
?
7. Draw a structural formula for the hemiacetal formed when one molecule of ethanol combines with one pentanal molecule.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
8. Draw a structural formula for the ketal formed when two molecules of ethanol combine with one 2-butanone molecule.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.

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https://brainmass.com/chemistry/organic-reaction-intermediates-and-mechanisms/reactions-carbonyl-compounds-587088

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Answer to 587088

1) Chromic acid (K2Cr2O7 in H2SO4) easily oxidizes aldehydes to corresponding carboxylic acids (-CHO to -COOH).
So the product will be:

The net ionic reaction is as follows:

where R = (CH3)2CH-

2) Tollens' reagent contains the diamminesilver(I) ion, [Ag(NH3)2]+. Aldehydes reduce the diamminesilver(I) ion to metallic silver, forming a grey precipitate of silver or a silver mirror on the test tube. Due to alkaline condition, the aldehyde itself is oxidized to a salt of the corresponding carboxylic acid. ...

Solution Summary

This solution provides missing products and starting materials of several organic reactions, with adequate general discussion and chemical structures.

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See Also This Related BrainMass Solution

10 Questions About Reactions of Carbonyl Compounds

The reaction of a carboxylic acid with an alcohol in the presence of acid is termed Fischer esterification.

1)
the nucleophile in this reaction is: _________

2)
compound C functions as ____________ in the reaction
a) neutralizer
b) catalyst
c) solvent
d) base scavenger

3)
Fischer esterification is an example of:
a) nucleophilic acyl addition
b) nucleophilic acyl substitution
c) nucleophilic acyl rearrangment
d) nucleophilic acyl elimination

4)
many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases catalyze hydration by:
a) converting the water to hydroxide ion, a much better nucleophile
b) making the carbonyl group less electrophilic
c) shifting the equilibrium of the reaction
d) making the carbonyl group more electrophilic

5)

Formulate a reasonable mechanism for the reaction of the cyanohydrin of benzaldeyhe, shown above, with aqueous NaOH. Show all intermediate structures and all electron flow with arrows.

6)

This reaction is a ___________ reaction.
a) 1,2-additon
b) direct addition
c) electrophilic addition
d) conjugate addition

7)

carboxylic acids are synthesized from alkyl halides via either grignard reagent carboxylation or nitrile hydrolysis.
What is the best method for effecting the following conversions? Explain the choice and if neither is appropriate, explain.

a)

b)

c)

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