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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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Reactions on alpha tetralone to synthesize naphthalene

Alpha-Tetralone is reacted by $1.\ce{Zn(Hg),HCl}\ \ 2.\ce{ Pd/C}$ What is the product and mechanism that is followed for the 2nd reaction? A book by SN Sanyal says that Naphthalene will be produced . ...
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54 views

Which one is the stronger base?

I'm studying Wolff-Kishner reduction and I don't understand why after this step the leaving group is $\ce{OH-}$ instead of $\ce{^-HN-NH2}$. I guess it's because hydroxide ion is less strong than the ...
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23 views

Organic reduction of alkene

Can Wolff Kishner and Clemmensen Method be used to reduce alkyne or alkene. If so do they produce syn addition or anti addition product. ?
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Does formaldehyde undergo Clemmensen reduction (Zn(Hg)/HCl)?

I can't seem to find the reaction anywhere on the net. Please explain why or why not.
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38 views

What are solvents that can dissolve sebum that is safe for topical use? [closed]

I do not know much about these properties and I need some feedback regarding these. Sebum is a semi-fluid that in humans contains a mixture of triglyerides, cholesterol, ester waxes, and squalene. 57....
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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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56 views

Reduction using sodium borohydride

When we react a ketone with NaBH4, it reduces to alcohol. I coudn't understand the mechanism of this reaction. The first step in my text book states that the hydrogen from NaBH4 attacts the carbonyl ...
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42 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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85 views

Why can't terminal alkynes take part in Birch reduction?

According to my book terminal alkynes are not observed in Birch reduction.Why is this so? The only property I know about them is that they are slightly acidic. Does this have something to do with it? ...
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43 views

Does clemmensen reduction work on amides?

I got a conversion in an examination for acetamide to ethylamine. I thought that since it has a carbonyl group Clemmenson might work and used $\ce{Zn\!:\!Hg + HCl}$. I saw the mechanism and didnt ...
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1answer
91 views

What side reactions are suppressed by the use of TMSCl in the acyloin condensation?

I was reading about the acyloin condensation and came across a statemant according to which, the use of TMSCl obviates competing reactions. My question is what kind of competing reaction would happen ...
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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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Conditions for the reduction of carboxylic acids by LiAlH4

From my textbook, the reduction of carboxylic acids by LiAlH4 "has to be in anhydrous conditions, such as dry ether, followed by aqueous acid." I read from the internet that the reduction reaction has ...
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1answer
46 views

Reduction of carbonyl group [closed]

A compound contains both alpha,beta unsaturated carbonyl group and a normal carbonyl group. Is there any method to reduce the normal carbonyl group keeping the alpha,beta unsaturated carbonyl group ...
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1answer
163 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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What is the difference between hydrogenation in presence of platinum and nickel catalyst?

This question is about the hydrogenation of an epoxide into an alcohol. I got option C as an answer, but the answer is option D as well. I have never seen the difference in reduction by change of ...
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39 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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1answer
210 views

Are there any reducing agents for reduction of nitrobenzene to aniline other than Sn/HCl?

I was taught that Sn/HCl should be used for reduction of nitrobenzene to aniline. Can I ask if there are any alternative reducing agents (for example, LiAlH4?) to do the same task?
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Organic reaction with Na2S2O4 [closed]

Question: In the first step due to cooperating Inductive and resonance effect C6H5N2 + will be attached at the ortho position of methyl group for which para position is occupied by Amine group ...
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1answer
130 views

What are the different types of catalysts used in catalytic hydrogenation of alkynes?

This is a question from Org. Chem. by Solomons, Fryhle & Snyder, adapted for JEE by M.S. Chouhan : In the first step, I expected that the reaction would stop at alkene formation via syn ...
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2answers
150 views

Can protection group be used in a Wolff–Kishner reaction?

How can I modify the ozonolysis of cyclohexene such that one of the aldehyde groups of the product, adipaldehyde, is efficiently protected as a base stable protecting group? I know that attempting to ...
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1answer
128 views

Reduction of 2-cyclohexenone to cyclohexanol

Is $\ce{NaBH4}$ a suitable reducing agent for the conversion of 2-cyclohexenone to cyclohexanol? In Clayden (page 506, second edition), I have found the reduction of cyclopentenone to cyclopentanol ...
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152 views

Do alkyl halides get reduced with hydrogen/nickel catalyst?

According to my textbook, alkyl halides can't be reduced to alkanes by the $\ce{H2/Ni}$ or $\ce{H2/Pd}$ reducing agents, and almost no other reducing agents other than $\ce{LiAlH4}$ reduce alkyl ...
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Why on loosing aromatic chracter still product produced is 90% in the following reaction? [duplicate]

In Birch reduction reactant loses it aromatic chracter but still the product found is to be 90%. By loosing aromaticity product must be less stable so less amount of product must be formed. Why ...
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2answers
55 views

Why is it a reduction from a ketone to an alcohol? [closed]

Why is it a reduction from a ketone to an alcohol (using $\ce{LiAlH4}$)? I'm not able to figure out the oxidation state of carbon.
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131 views

The reaction mechanism for epoxides to react with LiAlH4 [closed]

Does anyone know the mechanism for the reaction of epoxides with Lithium aluminium hydride (product of course being an alcohol)
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88 views

What is the product of the reaction of diol with tosyl chloride followed by lithium aluminum hydride?

This question is about the structure of products X and Y. According to me, the answer should be only A (as OTs will substitute on benzylic carbon). But in the answer key, they have given B and D. ...
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2answers
95 views

Out of the given reagents, find the ones to be used to convert benzene to p-aminophenol

$\ce{Br2/FeBr3}$ $\ce{CH3Cl/AlCl3}$ $\ce{KMnO4}$ $\ce{HNO3/H2SO4}$ $\ce{NBS}$/hv $\ce{NaOH}$ $\ce{Sn/HCl}$ $\ce{NH4SH}$ $\ce{NaBH4}$ I'm able to get the amino group onto the ring by using 4 and 7. ...
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1answer
132 views

Hydroboration oxidation reaction on trans,trans,trans-1,5,9-cyclododecatriene with carbon monoxide

The given solution: I got this question in an entrance exam coaching test paper in India. Product P is easily covered by the mechanism of simple hydroboration-oxidation reaction, and I've understood ...
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1answer
153 views

Why HF can't reduce H2SO2?

I read that $\ce{H_2SO_2}$ is an extremely unstable acid, so shouldn't even a weak reducing agent like $\ce{HF}$ be able to reduce $\ce{H_2SO_2}$ to $\ce{S}$ or something along similar lines?
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Can DIBAL-H reduce carboxylic acid? [duplicate]

Question : Can DIBAL-H (Diisobutylaluminium hydride) reduce carboxylic acid? According to "March's Advanced Organic Chemistry" (by Jerry March), acid can be reduced upto aldehyde using DIBAL-H. But ...
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1answer
76 views

Reduction of nitro compound using protection group

I've tried researching things like cyclisation, nitro reduction and all I've found is little to nothing. I know that for the 1st arrow I need to protect the carbonyl and the 2nd arrow is the ...
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1answer
479 views

Why is LiAlH4 a stronger reducing agent than DIBAL-H [closed]

Asides the different number of hydrogens, why is LiAlH4 a stronger and less selective reducing agent than DIBAL-H
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106 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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2answers
131 views

What will this compound produce when reacted with sodium borohydride?

I feel the answer should be this: Because the carbonyl carbon on the aliphatic chain should be more electrophilic than the one on the ring due to the presence of two neighbouring electronegative ...
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1answer
245 views

Reduction of nitro group to amine

In the above reaction, I do know that $\ce{SnCl2/HCl}$ reduces $\ce{-NO2}$ group to $\ce{-NH2}$ but which one of the two $\ce{-NO2}$ will be reduced first by $\ce{SnCl2/HCl}$? Why so? And how does $\...
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395 views

Does Sn/HCl reduce the carboxylic group of benzoic acid?

I googled, but couldn't find any proper answer. As far as i know, $\ce{Sn/HCl}$ is a mild reducing agent and reduces a $\ce{NO2}$ group of nitrobenzene into $\ce{NH2}$. But does it reduce the $\ce{...
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214 views

Does a non-terminal alkyne react with sodamide?

Hydrocarbon (A), $\ce{C6H10}$, on treatment with $\ce{H2/Ni}$, $\ce{H2}$/Lindlar catalyst and $\ce{Na}$/liquid $\ce{NH3}$ forms three different reduction products (B),(C) and (D) respectively. (A) ...
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481 views

Birch reduction of anisole

Hepworth, Waring and Waring (2002) mentions that: In general, electron-withdrawing substituents make the arene more susceptible to reduction, while the opposite applies for electron-donating ...
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1answer
404 views

Does RedP+HI reduce all carbon functional groups to alkane?

I've seen the related questions 1 and 2, they're not duplicates So. when introducing Red P+HI reduction, our teacher said that it is the strongest reducing agent, and it can reduce any functional ...
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52 views

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 ...
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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
182 views

What is the purpose of CaO in Oakwood reaction

In the Oakwood reaction, i.e. $$\ce{RCOOH ->[NaOH + CaO] RH + Na2CO3},$$ is there any role or importance of $\ce{CaO}$, because it doesn't appear to be anywhere in the product.
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Does DIBAL-H reduce carboxylic acids?

Diisobutylaluminium hydride(DIBAL-H) reduces only carboxylic acid, ester or both? The answer given was that it only reduces ester. Is it correct that under any condition carboxylic acids are not ...
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Reaction of phenol and zinc dust

There is a reduction reaction of phenol with zinc dust which is found in many books. $\ce{Ph-OH + Zn -> Benzene + ZnO}$ However, a simple google search fails to explain anything about the ...
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1answer
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Birch Reduction of Benzene

According to my Organic Chemistry Textbook: Benzene can be reduced to 1,4-cyclohexadiene by treating it with an alkali metal (sodium, lithium, or potassium) in a mixture of liquid ammonia and an ...
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Why does LiAlH4 reduce the double bond of cinnamaldehyde, whereas NaBH4 does not?

I read an answer here about why $\ce{LiAlH_4}$ does not reduce conjugated double bonds, and that $\ce{NaBH_4}$ does. But in the case of cinnamaldehyde, $\ce{LiAlH_4}$ reduces the conjugated double ...
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Why does the Rosenmund reduction stop at the aldehyde stage?

In the Rosenmund reduction, an acyl chloride can be reduced to an aldehyde by hydrogenation over a palladium catalyst poisoned with barium sulfate. Why isn't the aldehyde product further reduced to ...
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554 views

Are groups other than carbonyl reduced by Clemmensen reduction?

According to my textbook, Clemmensen reduction reduces only aldehydes and ketones to alkanes. But in this question: $\ce{Zn-Hg/HCl}$ has reduced both the ketonic and nitro group. Correct answer given ...
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384 views

Effect of protecting group on diastereoselectivity of LiAlH4 reduction of α-hydroxyketones

In the reactions above, taken from Tetrahedron Lett. 1982, 23 (23), 2355–2358, the choice of protecting group on the α-hydroxyl group has a large influence on the diastereoselectivity of reduction. ...