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 isn't the Leuckart reaction used to make (meth)amphetamine?

For example, in Breaking Bad, they synthesize meth from phenylacetone. Why not just use methylammonium formate, if they already have methylamine?
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Reduction of unsymmetrical ketones using BINAL-H (Enantioselectivity)

I am struggling with a problem regarding the enantioselectivity of BINAL-H for quite some time now. The reaction scheme shows the reaction with (S)-BINAL-H as it is observed plus the transition state ...
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Partial reduction of anthraquinone to anthrone using stannous chloride?

I've heard of using $\ce{SnCl2}$ in the Stephen's reaction where you reduce a nitrile down to an aldehyde. I've come across a laboratory manual that discusses using tin in the partial reduction of ...
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Acid hydrolysis of Birch-reduced Anisole

The following is a question from Advanced problems in organic chemistry by MS Chouhan: Product $A$ is rather straightforward: and on acidic hydrolysis, the following reaction takes place: Here the ...
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Why adding sodium bicarbonate quenches a reductive amination using sodium triacetoxyborohydride?

I'm planning to do a reductive amination reaction between methyl pyruvate and benzylamine using sodium triacetoxyborohydride, $\ce{NaBH(OAc)3}.$ Acetic acid is used as a catalyst for protonating the ...
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Chlorinated hydrocarbon destruction

What's a convenient method for lab-scale destruction of chlorinated hydrocarbons? Reductive dechlorination, total oxidation are fine as well as other routes you want to point out. If specific ...
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Why does BH3/THF reduce the carbonyl group to a methylene rather than an alcohol?

This reaction is taken from: Pintér, Á.; Sud, A.; Sureshkumar, D.; Klussmann, M. Autoxidative Carbon-Carbon Bond Formation from Carbon-Hydrogen Bonds. Angew. Chem., Int. Ed. 2010, 49 (29), 5004–5007. ...
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Does red phosphorus with hydriodic acid reduce all alkyl halides?

$\ce{HI/P}$ is used for reduction of alcohols, aldehydes, ketones and acids to alkanes. As for alkyl halides, I have read that only alkyl iodides are reduced, whereas other alkyl halides do not: $$\ce{...
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Reduction of orthoesters and acetals with LiAlH4

As I know, orthoesters react with $\ce{LiAlH4}$. After searching on the Internet I’ve found that acetals react with $\ce{LiAlH4}$ in the presence of $\ce{AlCl3}$. Why can’t acetals be reduced only in ...
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Naftiridine hydrogenation

I was reading an article about the synthesis of 1,2,3,4 tetrahydronaphtyridine and I found this image. I don't understand why the major product of hydrogenation is the less substituted and not the ...
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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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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2 answers
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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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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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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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6 votes
2 answers
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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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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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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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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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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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8 votes
1 answer
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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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8 votes
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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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1 answer
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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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9 votes
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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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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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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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