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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Why do different products form when alkali halide reacts with zinc in polar protic and aprotic solvents?

Let's take an alkali halide such as $\ce{CH3CH2Cl}$ the two reactions in polar protic and aprotic solvents are as follows: $$ \begin{align} \ce{CH3CH2Cl &->[Zn, CH3OH] CH3CH3}\tag{R1} \\ \ce{...
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Does lithium aluminium hydride react with conjugated dienes? [closed]

I have searched many websites, but was unable to find if $\ce{LiAlH4}$ is able to reduce conjugated dienes, such as styrene to ethylbenzene or 1,3-butadiene to 1-butene.
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What is the major product in the reaction between 4-chloropentanal and lithium aluminium hydride?

What would be the major product between 4-chloropentanal and $\ce{LiAlH4}$? After the reduction of the aldehyde, would the hydroxyl group formed at $\ce{C-1}$ attack $\ce{C-4}$ causing cyclization to ...
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50 views

Conjugated diene + Na in liq.NH3 [duplicate]

I learned that alkynes gets reduced on addition of $\ce{Na}$ in liquid $\ce{NH3}$ to form alkenes (which is not further reduced). Recently I came across a reaction where a conjugated diene was treated ...
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Reactivity order of DIBAL-H and diborane with esters and acids

I have been taught in class that DIBAL-H is more reactive towards esters than carboxylic acids while opposite is true for diborane. Also DIBAL-H mentioned is taken under low temperatures (−78 °C). I ...
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Why negative charge delocalises away from electronegative atoms

In the mechanism for the Wolff-Kishner reduction, after the $\ce{OH-}$ abstracts a proton, the resulting negative charge delocalises away from the nitrogen atom to the carbon, and the subsequent ...
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216 views

On the use of hexane in the organic reduction by DIBAL-H

In some variations of the organic reduction by DIBAL-H, I've seen hexane used, as in this equation from this website; I've looked it up, but I haven't seen any explanation for why hexane's used there....
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What reagents are used to selectively reduce 2,2,3‐trimethyloxirane to secondary and tertiary alcohols?

Problem Answer Questions I know $\ce {LiAlH4}$ is a reducing agent because it gives four $\ce{H-}$ and will attack on our reactant on carbon with less substituents, i.e. in this case on $\ce{-CH-}$ ...
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1answer
80 views

Birch reduction in diethyl ether [closed]

I wanna ask, why I can't find any experiment using amonia dissolved in diethyl ether. You could bypass need of cooling the amonia under it boiling point by gassing the amonia to diethyl ether. Why it ...
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99 views

How is the hydrazone formed in the Wolff-Kishner reduction?

In the Wolff-Kishner reduction the first step is to react a carbonyl with hydrazine to form a hydrazone. The later steps of the reaction requires a strong base to cause loss of nitrogen. However, the ...
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70 views

Why can't sodium borohydride reduce carboxylic acid and ester groups? [duplicate]

Sodium borohydride ($\ce{NaBH_4}$) is a reducing agent used in various organic reaction to reduce aldehydes, ketones and acyl chlorides. Why can't sodium borohydride reduce carboxylic acid groups and ...
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1answer
118 views

Can sodium borohydride reduce hemiacetals?

In the synthesis of Panacene by Canesi et al. [1], a step involves the installation of an $\ce{-OH}$ group on a double bond, using the oxymercuration-demercuration procedure. However, the product ...
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Why can't NAD+ undergo single-electron reduction?

$\ce{FAD}$ can undergo single-electron reduction to form a stable radical, which can then be reduced again to $\ce{FADH2}$. This is supposedly possible due to resonance stability, where the unpaired ...
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263 views

Why does Birch reduction of naphthalene with isoamyl alcohol form tetralin instead of 1,4-dihydrodialin (as formed with C2H5OH)?

I recently came across this question, which required me to know the difference between performing a Birch reduction on naphthalene using ethanol and using isopentanol. Why does using isopentanol lead ...
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229 views

Clemmensen reduction of α-, β-keto acids

The following is from Organic Chemistry-2 for JEE Advanced by KS Verma: α- or β-keto acids do not undergo Clemmensen reduction. My reasoning was that the double bonds are in conjugation which makes ...
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Why does hydrogenation of this compound not result in a diastereomeric mixture? [duplicate]

In a question, this compound was given and it was asked: "Hydrogenation of the above compound in the presence of poisoned Palladium catalyst gives?" When I was answering it, I thought that ...
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1answer
94 views

Reduction of alcohol to alkane [closed]

I have been looking everywhere for hours now, and can't find anything on a simple lab reduction of an alcohol to an alkane that doesn't involve any "fancy" reagents such as tosylates, metal ...
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Does reduction of carbonyls using borohydride ever use NaOH in the reaction?

I was reading about borohydride reductions of aldehydes and ketones in one of the Clayden textbooks, and I saw that NaOH was used in the bottom reaction for some reason: Is this really necessary? I ...
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1answer
483 views

Photochemical reduction of benzophenone: why inverted flask?

I've come across an interesting protocol for photochemical reduction of benzophenone to benzhydrol (diphenyl methanol) with sodium alcoholate in alcohol, the 2nd protocol in https://prepchem.com/...
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Elimination vs reduction reactions - how to tell

Here are two compounds: Compound H: and compound I: Compound H reactions with the reagent shown below to form compound I and two other products. How would you clarify this reaction? I thought it was ...
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In aldehydes with an alkene substituent, what conditions favor Wolff–Kishner reduction over Clemmensen reduction?

This module I am answering asked me to provide a reason why Wolff–Kishner reduction is favored over Clemmensen reduction in reducing (3Z)-pent-3-enal to (2Z)-pent-2-ene but either Wolff–Kishner or ...
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Reaction mechanism of tin(II) chloride to reduce nitrobenzene to aniline [duplicate]

Does anyone know the reaction mechanism for $\ce{SnCl2}$ to reduce nitrobenzene to aniline? I can only find $\ce{Sn/HCl}$ reaction mechanism but can't seem to find any information on $\ce{SnCl2}.$ ...
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I need to reduce the Nitrile group without affecting the boronic acid. How to do that?

I need to Reduce the Nitrile group (CN) in the (3-cyanophenyl)boronic acid in to a primary amine without disturbing the Boronic acid group.Using LAH can trigger reduction of Boronic group. what are my ...
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Why NaBH4 don't reduce this keto group?

I was solving problems related to Carbonyls. The question was: What would be the product formed after the reduction of this compound using $\ce{NaBH4}$? (This is an isomer of Glutaric Anhydride) I ...
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Does DIBAL-H reduce alcohol?

Does DIBAL-H reduce alcohol? I was reading an article by Rentsch and Kalesse [1] and I came across this reaction, but could not figure out how the final compound is formed: Reference Rentsch, A.; ...
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Reducing olefinic bond in conjugation with C=O bond using LiAlH4

I'm studying the synthesis of alcohols. One of the methods given is "Reduction with metallic hydrides like $\text{LiAlH}_4$". Under this title the following reaction has been listed [1, p....
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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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1answer
318 views

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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1answer
153 views

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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71 views

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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1answer
166 views

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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1answer
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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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2answers
233 views

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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1answer
138 views

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
667 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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1answer
54 views

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
270 views

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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1answer
1k views

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 ...