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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42 views

How does deprotonation works?

I've been studying organic chemistry and came across this example : CH3-CH2-CH(+)-CH3 ---> CH3-CH=CH-CH3, the explanation the textbook gave was related to deprotonation. I've tried drawing lewis ...
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2answers
91 views

Reaction mechanism of phenylhydrazine with carbonyl

I am currently working on the following problem, but I don’t know how it is solved: I guess it is a Fischer-Indol synthesis, but I am not sure. This is what I got: Any help would really be ...
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1answer
29 views

Where does Aluminum Hydroxide come from in a reduction of a ketone by LAH? [closed]

The experiment was done in a Laboratory. A ketone was reduced with LAH in THF under reflux. At the end of the reaction, the protocol stated to add water until there is no more H2 released. The H2 ...
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36 views

Selective reduction of aromatic nitro group

In the following compound, is it possible to selectively reduce the aromatic nitro group to an amine, as shown in the reaction? I fear that the methods usually used to reduce aromatic nitro compounds,...
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1answer
72 views

Are terminals alkyne reduced by Na/liq NH3? [closed]

By the mechanism, it appears that any alkyne should be reduced, but I couldn't find any source supporting or disapproving it. One possibility is that first acid-base rxn takes place but still the ...
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1answer
87 views

Hydrogenation of pent-4-en-2-one

If one equivalent of $\ce{H2}/\ce{Pt}$ is made to react with one equivalent of pent-4-en-2-one, what will be the product formed?
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1answer
114 views

Method to remove impurities from acetaminophen synthesis experiment

I'd like to know about impurities from acetaminophen synthesis experiment. Are there any impurities produced by oxidation of p-aminophenol? If there is any impurity produced by oxidation of p-...
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0answers
79 views

How is this Clemmensen Reduction taking place? [closed]

How did that isotopically labelled Carbon migrate? I know that an carbanion is formed, but I am not able to conclude the final product. Please Help
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1answer
117 views

Dextrose equivalent values (DE) of the most common sugars

What are the dextrose equivalent values (DE) of lactose, and other common sugars? Some data like the values for sucrose (0), maltodextrin (x<20), maltose (52), and glucose (100) can be found at ...
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1answer
47 views

Sodium metal and alcohol reduction of imines. Is it possible?

It is known that sodium metal in ethanol with toluene under reflux can reduce nitriles to amines1 and can also reduce oximes and schiff bases to primary amines and secondary amines respectively2. Is ...
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2answers
306 views

Can Mg/ether reduce carbonyl groups?

One of the ways of preparing Grignard reagent is: $\ce{R-X ->[Mg/ether] R-MgX}$ However let's assume that a carbonyl group is present along with a halide in the substrate. Will $\ce{Mg/ether}$ ...
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1answer
120 views

Reduction of conjugated ketone with lithium aluminium hydride

I came across a question about reduction of a conjugated ketone with $\ce{LiAlH4}$. Although it seemed quite easy at first sight, everything became cloudy as I dug deeper. My doubts regarding the ...
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1answer
108 views

Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?

The major product obtained in the following reaction is: Question source: JEE Main 2019 The molecule shown as product is the official answer given by JEE from the given options. I have written the ...
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1answer
136 views

Why does LiAlH4 reduce the double bond of cinnamaldehyde, whereas it does not reduce the double bond in crotonaldehyde?

$\ce{LiAlH4}$ is a strong reducing agent capable of breaking the double bonds. It does break the double bonds in cinnamaldehyde. Shouldn't $\ce{LiAlH4}$ be able to break the double bond in ...
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49 views

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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290 views

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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0answers
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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58 views

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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39 views

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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1answer
294 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
114 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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1answer
139 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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1answer
274 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
162 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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41 views

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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1answer
885 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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1answer
305 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
116 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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51 views

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
498 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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174 views

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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34 views

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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108 views

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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61 views

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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1answer
432 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
209 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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1answer
49 views

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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1answer
67 views

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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62 views

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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74 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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53 views

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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203 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 ...