Questions tagged [organic-reduction]

For questions about reduction reactions in organic chemistry, where a molecule of interest is reduced. Do not use for questions on general redox concepts.

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Can propylene glycol be converted to just propylene? [closed]

If so, what would the process be like? How about ethylene glycol? Are either of these processes ever done on an industrial scale? It seems to me that removing both oxygen atoms would be fairly ...
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What are the unique reactions of conjugated carbon containing carbonyl compounds?

Various sources give different ideas about the reduction reaction of α,β-unsaturated carbonyl compounds which have conjugated carbon. Just like cinnamaldehyde do aliphatic α,β-unsaturated carbonyl ...
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How does Al-Hg react with carbonyl in presence of concentrated HCl?

In Clemmensen reduction, $\ce{Zn-Hg}$/ $\ce{ conc. HCl}$ reduces the carbonyl $\ce{>C=O}$ to $\ce{>CH2}$, by the following mechanism(?): What happens to the carbonyl group if we replace Zinc ...
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Reduction of epoxide

Does $\ce{LiAlH4}$ and $\ce{NaBH4}$ reduce an isolated epoxide? I have two books where both are saying differently. One says it can and other says cannot. On searching the web there was no definite ...
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Reduction by Activated Carbon

Does reduction by carbon itself occur when filtration is performed using activated carbon? Is it part of the central mechanisms involved in activated carbon filtration? One of the specificities of all ...
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What are acid/base sensitive groups?

My textbook says that Clemmensen Reduction cannot take place in the presence of an acid-sensitive group and the Wolf Kishner reaction won't happen in the presence of a base sensitive group, citing $\...
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What is the influence of glass type on silver mirror making?

I'm considering the reaction wherein ionic silver (from the dissolved nitrate) is reduced by glucose in the presence of NaOH and forms a metalic silver layer on glass. Reading through several topics ...
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Function of sodium amalgam and CO2 in formation of aldohexose

There is this following conversion in my book: $$\gamma-\text{Lactone}\ce{->[Na/Hg +CO2]}\text{Aldohexose}$$ I'm not sure how this reaction takes place. I searched for mechanisms and couldn't ...
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Synthesis question: Using reductive amination to form pyrrolidine

What molecule results from treating 4-oxopentanal with $\ce{NH4Cl}$ and $\ce{NaCNBH3}$? Why? Is this a good, high yield reaction? I believe that pyrrolidine is formed because amination will convert ...
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Reagent to reduce aliphatic aldehyde to alcohol while protecting double bond

I have a straight chain, aliphatic aldehyde (liquid) with a double bond in it. I want to reduce the terminal carbonyl group to an alcohol but without touching the C=C double bond. The double bond is ...
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Conversion of Erythrosine to Fluorescein

I am a home-chemist and I love dyes. I recently got my hands on sodium salt of erythrosine (tetra-iodinated fluorescein). I want to convert erythrosine to fluorescein. I speculate that using dilute ...
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Birch reduction of 1,2-Cyclopentanedione and Diketones

This answer given to this problem was that only one of the double bonds is reduced into an alcohol. I think i understand how the double bond is reduced into an alcohol. An electron is transferred to ...
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Mechanism for simultaneous reduction of nitro group (into aniline) and aromatic substitution (into benzonitrile) by Ethyl cyanoacetate?

I stumbled upon this paper when I'm trying to look at established protocol to synthesize one of the compounds (compound IIk) mentioned in the paper. Studies on Aromatic Nitro Compounds. V. A Simple ...
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Red P+HI reduction [duplicate]

My teacher told us that Red P and HI can reduce any functional group. Is it true? Or are there any groups it can't reduce?(I know this exact question has been asked before but I couldn't find the ...
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Reduction of carbonyl compound by LAH (in anhydrous ether) followed by reaction by acidic water

What will be the final product upon reaction of $\ce{CH2=CH-CH2-C6H4-CH=CH-CHO}$ with $\ce{LiAlH4}$ (in dry ether) followed by acidic water? LAH will reduce the carbonyl group to alcoholic group and ...
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Effect of clemmensen reagent on 4-oxo-4-phenylbutanoic acid

When I first solved the question, I had reduced the ketonic group. Then as the medium is acidic the -OH in carboxylic acid, will get protonated and there will be formation of stable carbocation and it ...
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What will be the product of following Wolf-kishner reduction?

Question Attempt 1.Wolf kishner would reduce double bond oxygen to alkane. 2.Also since water is present acetal should break. 3.SnAr doesn't seems possible due to adjacent bulky groups. So ...
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Reduction of (4-methylcyclohex-3-en-1-yl)methoxymethylbenzene to 4-methylcyclohex-3-en-1-ol

Find the suitable reagent to carry out the following transformation: The answer provided says that $\ce{H2/Pd-C}$ can be used to bring about the given transformation, but I am failing to understand ...
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Reducing power of ammoniated electrons

I came across a question asking which of the following conversion/reductions can be accomplished using ammoniated electrons. $\ce{O2}$ to $\ce{O2^{2-}}$ $\ce{K2[Ni(CN)4]}$ to $\ce{K4[Ni(CN)4]}$ ...
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1answer
179 views

Reductions by Na + EtOH

According to my chemistry teacher, sodium in ethanol can reduce ketones, aldehydes, acid halides, esters, cyanides, isocyanides, nitro compounds and acid anhydrides. Now surfing over the web, I could ...
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Reduction of only double bonds

In the conversion shown below I need to find B . Initially I thought of protecting the carbonyl group using ethylene glycol and then carry out reduction of double bonds using hydrogenation but it is ...
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Reduction of nitrobenzene in alkaline medium

My teacher listed out the following set of reactions under the aforementioned topic: He explained the formation of azoxybenzene as follows. Reduction of nitrobenzene produces 2 intermediates: ...
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1answer
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Are alkenes or alkynes reduced first with diimide?

I know that $\ce{NH2NH2}/\ce{H2O2}$ is used as an reducing agent for selective reduction of alkenes and alkynes. $\ce{NH2NH2}$ reacts with $\ce{H2O2}$ to form diimide ($\ce{N2H2}$), which then ...
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Chirality and number of sterioisomers

I have recently read that the number of sterioisomers in a compound having n chiral centres is 2^n. (That is, if no meso form is present) The below question asks for the number of sterioisomers in ...
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Action of KMno4/H+ and heat in this reaction

The first step uses LAH which is a hydride donor. So H- attacks any one carbonyl carbon and forms an aldehyde and acid attached to the ring. Then Conc. KMno4 is used. As far as i know, it cleaves c=c ...
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does Hydrogen and nickel reduce c=c

In my course, I've come across H2 and Ni catalyst as a reducing agent for alkenes and LiAlH4/NaBH4 as a reducing agent for carbonyl groups. I know LiAlH4/NaBH4 can't reduce c=c as it is nucleophilic ...
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Organic chemistry [closed]

Could someone tell me what happens when a compound having a benzene ring reacts with a mixture of NaOH/HCHO? What reaction and mechanism does this follow?
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CuS+HCl is it a reduction or oxidation reaction

How do we identify whether a reaction is oxidation or reduction and please let me know whether the equation given above is oxidation or reduction.
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Specific reduction of certain functional groups

Consider the compound $\ce{Alkyl-(4 oxocyclopent-2-ene)carboxylate (A)}$. For example consider- Now consider the operations: $\ce{1. (A) + (i)BH3/THF (ii) H+}$ $\ce{2. (A) + H2/Pt}$ ...
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How long does it take Freon refrigerant to disappear from a room after an accidental major leakage?

I would like to know please how long does it take Freon refrigerant to completely disappear from a room after an accidental major leakage? Does it stick to surfaces , clothes or walls? Does natural ...
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1answer
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Converting cyclic compounds to their corresponding aliphatic compounds

Is there any reaction available to convert cyclic compounds to their corresponding aliphatic compounds? eg. Converting cyclohexane to n hexane
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Reduction of an Allylic Enoate to afford allylic alcohol in presence of Benzyl Acetal Groups

I have a question that requires finding a reagent for the reduction of an enoate to the corresponding allylic alcohol. Preferably done in one step too with an acid workup at the end too. What types ...
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Selective reduction of nitro group to amine, in benzene ring containing nitrile?

I would like to know if there is a possible route of synthesis that may reduce the shown compound A to the following product B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
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Reduction of amino acids to corresponding amino alcohols

I've stumbled upon an interesting article about reduction of amino acids and from there to reduction of L-valine to L-valinol using $\ce{LiAlH4}$ in THF. Article says that because of the cost of $\...
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Dissolving Metal Reduction of 4-Octyne to (E)-4-Octene and What Else?

I was reading Solomon's Organic Chemistry and came across the Dissolving Metal Reduction of 4-Octyne to (E)-4-Octene. (The same as can be found this question) But the book states that the (E)-4-...
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Reduction of carbamate with LAH

The products of the reduction of esters with $\ce {LiAlH4}$ and the products of the reduction of amides with $\ce {LiAlH4}$ are vastly different. The former reduction cleaves the ester and produces ...
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Are chlorinated solvents generally avoided in reducing reactions?

Are chlorinated solvents incompatible with reducing reagents? Is reductive dechlorination the reason? There also seems to be exemptions, in J. Org. Chem. 1996, 61, 3849-3862, 1,2-dichloroethane was ...
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Reduction of ester / eneone in presence of epoxide

I want to reduce an ester and an eneone in the presence of a terminal epoxide. I read on here @jerepierre did an ester in the presence of an epoxide with DIBAL. I know the DIBAL works for my ester, ...
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Diborane reduction

I am stuck at a step in reduction of alkene using $\ce{B2H6}.$ I assume that step 1 is the addition of borane to alkene. After that a water molecule attacks $\ce{-BH2},$ it being a Lewis acid. ...
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Which of these reactants will not generate this racemic amine?

I understand that in E there is no electrophile the amine can attack, however, I do not understand why A is an answer as well. The amine in A can perform an intramolecular attack on the aldehyde and ...
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Chemical Reaction Alternative to O2 Respiration in H2/N2 Atmosphere [closed]

Note: If this question does not belong on this Stack Exchange, please direct me to a more appropriate Stack Exchange. This is a "creative chemistry" question as much or more-so than a "give me the ...
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Reduction of conjugated double bond by sodium borohydride

Some of my teachers were debating about whether a double bond in conjugation with a ketone is reduced or not by $\ce{NaBH4}.$ One of my teachers presented the evidence from Clayden which had an ...
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Rationale behind Barton's rules for catalytic hydrogenation

Organic Chemistry by Morrison and Boyd,Seventh Edition says - When cyclohexanones are used as substrates, the stereoselectivity of the reduction is found to be dependent on the acidity or the ...
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Which functional group gets reduced first?

The following is a reduction reaction. In the reduction of 2 to 3, keto group undergoes reduction by nucleophillic addition. Ester could undergo nucleophillic acyl substitution to give an aldo group, ...
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603 views

Could sodium in ethanol reduce amides to amines?

Strong reducing agents like $\ce{LiAlH4}$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn ...
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Fehling's solution - What is the shelf life of the unmixed A & B components?

If you prepare two separate solutions of Fehling's A and Fehling's B, what is the shelf life likely to be? Will the effectiveness of the solution diminish over time? The literature recommends ...
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Names of NAD+ and NADH

As part of the biochemical process of glycolysis, NAD+ is reduced to NADH. In other words, nicotinamide adenine dinucleotide is reduced to... nicotinamide adenine dinucleotide? Everywhere I look ...
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Dehydration of carboxylic acids with phosphoric acid

To find Z one must find X. Finding Y is of no use to find Z. I get X as: After addition of $\ce{H2/Pd-C}$, the unsaturated portion becomes saturated and the carboxylic acid remains unchanged. ...
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The products of a chain reaction beginning with acetone and sodium amide

I encountered the following question in an exam: $\ce{CH3COCH3 + NaNH2}$  giving out $\ce{A}$. $\ce{A}$ then reacts with $\ce{C2H2}$ giving out $\ce{B}$. $\ce{B}$ then reacts with $\ce{H+}$ to ...
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Efficient way to synthesize poly(alkyl)amine

I am trying to synthesize poly(ethylene-propylene)amine, i.e.: I've read that Reductive Amination is efficient regarding the reaction yield. However, it needs aldehydes to start the reaction. To make ...