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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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In what cases can LiAlH4 reduce alkene, or alkyne?

Lithium aluminium hydride $(\ce{LiAlH4})$ is known for its vast usability as reducing agent since it can reduce almost any organic functional group to alcohols, amines etc. Despite being so versatile, ...
Ansh's user avatar
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Why do halobenzenes not give Birch reduction?

I was studying Birch reduction and my book says halobenzene and phenol do not give Birch reduction. I want to know why these two type of compounds do not give Birch reduction. I also want to know if ...
Abhijeet Singh's user avatar
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What is the full mechanism for the controlled reduction of an alkyne using LiAlH₄?

Was going through my notes and realised I didn't completely fill them in. The first few steps I think are quite self-explanatory but I'm really confused about the last step where I go from the five-...
ajk's user avatar
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Why doesn't β-elimination occur in Cr(CMe3)4?

By $\beta$-elimination, I am refering to the reaction where a M-C-C-H structure reduces to ($\eta^2$-alkene)-M-H. My lecture notes claim that $\ce{Cr(CMe3)4}$ is stable and does not incur such ...
이희원's user avatar
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Electrolytic reduction of nitrobenzene in differing media

In my lecture notes it is given that in a weakly acidic medium, nitrobenzene on electrolytic reduction gives aniline, which makes sense to me because there is ample H+ in the medium to continue adding ...
Gaurav Sai Maddipati's user avatar
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How does the Eschweiler Clarke reaction occur with sodium cyanoborohydride as a reducing agent?

I am specifically confused with 2 concepts. How sodium cyanoborohydride acts as a reducing agent. I read that it acts as a source of hydride but I am not sure how this works. If anything, I assumed ...
glowabit's user avatar
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Reagent for conversion of 1-phenylpent-1-en-3-one to 1-phenylpent-1-en-3-ol

This conversion was recently asked in the NSEC, an Indian (preliminary) chemistry olympiad for high schoolers and the official answer key stated LiAlH4 is the correct reagent to be used. However I ...
Gaurav Sai Maddipati's user avatar
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Is this mechanism of reduction using LiAlH4 followed by hydrolysis of an amide correct?

Hello everyone. I had been given a question on reducing an amide group into an amine group using any reagent I saw fit as homework. I had used LiAlH4, which provides H- and does an acid base reaction ...
OrganicGod's user avatar
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2 answers
1k views

Does H2, Pd/C reduce a conjugated ketone?

Would H2, Pd/C be a sufficient reagent for this reaction to proceed? The question is from a test which asked what would be the most suitable reagent for the above reaction
Patrick Schick's user avatar
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What is the product and mechanism of reducing a cyclohexanone derrivative with LAH?

I've been trying to figure out the product and mechanism of the reaction pictured below for a while now: I'm fairly sure that the first step is the reduction of the ketone by LAH, which results in a ...
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Reduction of di-N-substituted imidazole to imidazoline to remove counterion?

I would like to synthesize a di-N-substituted imidazole (compound 4) in its free base form or reduce it to generate an imidazoline (compound 5) to remove the bromide counterion to the imidazole ring. ...
toodles's user avatar
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Reduction of benzylic alcohol and halide using H2 and Pd

I am studying drug synthesis, and I found some examples that uses $\ce{H_2}$ and Pd/C or Pd/$\ce{BaSO_4}$ as catalytic hydrogenation reagents for reduction of alcohol or halide in benzylic position. ...
Krang Lee's user avatar
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What determines the location of nucleophilic attack on a conjugated ketone or aldehyde?

In a conjugated ketone or aldehyde, nucleophiles could attack the double bond or the carbonyl carbon. I have two examples that differ in the location of initial attack, and I am wondering what ...
Kavin Ishwaran's user avatar
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How do I make this terminal alkyne into a methyl alkene on the third carbon?

How do I get from but-3-yn-1-ylbenzene to (3-methylbut-3-en-1-yl)benzene? I have tried $\ce{NaNH2}$ in $\ce{CH3Br}$ and then $\ce{H2}$ with a Lindlar catalyst, but that adds the methyl group at the ...
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How can I protect the ester group from reduction? [closed]

If I process this reaction the NaBH4 will also reduced the ester group to alcohol. I want to convert the Nitro (-NO2) functional group to Amine (-NH2) without disturbing the Ester group. So, my ...
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Conditions for Pd/C reduction of alkene

I am trying to do a $\ce{H2}$ reduction of cyclic alkene (otherwise simple hydrocarbon with 1 methyl group along with the chain about the weakly-strained cycle) using $\ce{Pd/C}$, the cycloalkene ...
Greg's user avatar
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1 answer
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Why does DIBAL-H not reduce esters to alcohols directly?

This source says that DIBAL-H reduces esters to aldehydes. Further, it says that, like NaBH4, it reduces aldehydes too. Why in reduction of ester, the aldehyde so formed is not converted to alcohol, ...
Answer_Me's user avatar
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What is the effect of NaNO2/HCl at 0-5° C on Nitro group?

In this particular reaction firstly $\ce{NaNO2/HCl}$ at $\pu{0-5°C}$ was taken and after that $\ce{H2/Ni}$ . But what I doubt is, was there any role of $\ce{NaNO2/HCl}$ at $\pu{0-5°C}$ ? Since only ...
Mridul Kumar's user avatar
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Does sodium borohydride reduces alkyne? [closed]

Will an isolated Alkyne or an alkene be reduced using sodium borohydride ($\ce{NaBH4}$)?
Mridul Kumar's user avatar
2 votes
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118 views

Red P+HI with some specific functional groups

I've seen the related question (Does RedP+HI reduce all carbon functional groups to alkane?). Although the question is admittedly similar, neither the answer provided nor the document linked in it ...
Skahoot's user avatar
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Rearrangement vs. Ring Strain in Cyclobutanecarboxaldehyde Nucleophilic Reaction

Predict the major product of the following reaction: Note: Product A is incorrectly marked as secondary halide, it should have been primary halide This question appeared in an national level ...
Prajval K's user avatar
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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?
kvanderfluegh's user avatar
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1 answer
387 views

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 ...
marsem's user avatar
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4 votes
2 answers
746 views

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 ...
Luca's user avatar
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3 votes
1 answer
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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 ...
Lost Anisole's user avatar
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1 answer
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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 ...
Ronnie Liu's user avatar
1 vote
0 answers
58 views

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 ...
Lorenzo Lami's user avatar
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1 answer
481 views

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. ...
Eastman CAO's user avatar
3 votes
1 answer
629 views

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{...
Ayush Shankaram's user avatar
2 votes
0 answers
107 views

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 ...
Ann Ivanov's user avatar
2 votes
0 answers
50 views

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 ...
Mamelandro's user avatar
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0 answers
203 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 ...
Fr0zen's user avatar
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-1 votes
2 answers
247 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 ...
maschine's user avatar
-1 votes
1 answer
42 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 ...
A math eur's user avatar
1 vote
0 answers
359 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,...
FusRoDah's user avatar
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1 answer
668 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 ...
Govind's user avatar
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1 answer
145 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?
Ilovemath's user avatar
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1 vote
1 answer
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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-...
조예원's user avatar
4 votes
0 answers
89 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
Sharad Kothari's user avatar
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1 answer
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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 ...
Constantthin's user avatar
5 votes
1 answer
368 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 ...
Jack's user avatar
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5 votes
2 answers
813 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 $\ce{Mg/ether}$ ...
Ashish's user avatar
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3 votes
1 answer
2k 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 ...
Cyclopropanol's user avatar
1 vote
1 answer
1k 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 ...
Jay's user avatar
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9 votes
1 answer
716 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 ...
Anonymous's user avatar
3 votes
0 answers
57 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{...
Ashish's user avatar
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3 votes
0 answers
55 views

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.
Yash Aggarwal's user avatar
7 votes
2 answers
447 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 ...
Kasonja Hill's user avatar
3 votes
0 answers
54 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 ...
Neelarghya Kundu's user avatar
6 votes
0 answers
273 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 ...
Satya's user avatar
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