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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Is there an advantage to the Clemmensen or Wolff-Kishner reductions over the Mozingo reaction?

As I understand it (and please correct me if I'm wrong), ketones and aldehydes can be reduced to methylene derivatives via: Clemmensen Reduction (acidic conditions): Wolff-Kishner Reaction (basic ...
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1answer
671 views

Why does reduction using sodium borohydride require a protic solvent?

Recently, I was looking at the chapter on chemoselectivity in Clayden et al.'s Organic Chemistry (2nd ed.). On p. 530, it is mentioned that sodium borohydride reduction only occurs in protic solvents ...
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How do popular reducing agents react on compounds that have ester, carbonyl, and unsaturated functionalities?

Suppose we have a chemical compound like ethyl 4-oxo-2-cyclopentene-1-carboxylate It is $\ce{-COOC2H5}$ bonded to a five-membered carbon ring with one double bond and the ring has another carbonyl ...
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Reaction of alkyne with sodium in ethanol

What is the product obtained on the reaction of but-2-yne with $\ce{Na}$ in ethanol? I know that $\ce{Na}$ in liquid $\ce{NH3}$ converts an alkyne to an alkene by anti addition, and $\ce{Na}$ in ...
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179 views

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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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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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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159 views

Addition of NaBH4 and LiAlH4

NaBH4 and LiAlH4 will be a source for the hydride ion and reaction will begin with addition of hydride by displacing the carbonyl group. But I am not sure will it attack both the carbonyl or only one....
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244 views

Help with a reaction: naphthalic anhydride to diol with LAH

First time asking a question but I've been trying to perform this reaction: for quite a while now. Most of the times I've only gotten this far: Here is the procedure I've been following: Dry THF (20 ...
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1answer
46 views

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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38 views

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 ...
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108 views

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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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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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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28 views

Using Wilkinson's Catalyst to reduce esters?

I was solving some questions on alcohols when I came upon a question in which it was asked that whether esters can be reduced using hydrogen in the prescence of wilkinson's catalyst. Now I know that ...
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Organic Chemistry - Reduction

Can anybody help me with the product? Seems like Birch reduction, but Birch reduction is used for conjugated systems and alkynes.
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291 views

How does DIBAL-H react with acid anhydrides?

I know DIBAL-H reduces carboxylic acids and some derivatives, but couldn’t find out about its reaction with acid anhydrides. Do these react? And what are the by-products (if any)?
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Can H– act as a strong Brønsted base like CH3–?

In the reduction of carboxylic acids with $\ce {LiAlH_4}$ we get an alcohol. But isn't there a possibility of the hydride donor abstracting $\ce {H^{+}}$ from the acid to form $\ce {H_2}$?
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1answer
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Mechanism of the Gatterman Reaction

Aryl diazonium salt on treatment with copper and the corresponding hydrohalic acid, gives the aryl halide. This reaction is called the Gatterman reaction. What is the mechanism of this reaction? Is ...
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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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35 views

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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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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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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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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43 views

Why do α- and β- Keto acids with Ph groups are generally not reduced,but other keto acids are reduced?

The reactions that I am thinking about: Ph here is for phenyl group I tried to do this by using the nakayabashi mechanism but could not find any resonance structure or anything special.I also thought ...
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35 views

Cross Cannizzarro reaction for ketones

I want to ask that cross cannizzarro could be possible between any aldehyde + ketone mixture(without alpha H) and we get products as aldehyde get oxidised and ketone get reduced(along with self ...
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284 views

Which functional groups are not reduced by DIBAL.H?

According to the table here, diisobutyl aluminium hydride can reduce amides to aldehydes but according to the data given to me by my teacher DIBAL.H cannot reduce: amides, acids, isocyanides and ...
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Prevent/Slow down oxidation of organic material

I'm having the hobby to draw paintings with the tea I drink trough the day. Usually I pour a tablespoon of the hot tea away, wait until it dries and gets more concentrated, so the colour is more ...