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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Reduction of conjugated double bond by sodium borohydride

Some of my teachers were debating about whether a double bond in conjugation with a ketone is reduced or not by $\ce{NaBH4}.$ One of my teachers presented the evidence from Clayden which had an ...
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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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62 views

Could sodium in ethanol reduce amides to amines?

Strong reducing agents like $\ce{LiAlH4}$ can reduce amides to amines. Sodium in ethanol (as a source of protons) is also a very strong reducing agent. Could it be therefore used to, for example, turn ...
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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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Thermodynamic data related to diazotization reaction

Is there any thermodynamic data available for diazotization of aniline and also for the reduction of the diazonium salt using sodium sulfite? I also want to know the heat of reaction for both the ...
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Names of NAD+ and NADH

As part of the biochemical process of glycolysis, NAD+ is reduced to NADH. In other words, nicotinamide adenine dinucleotide is reduced to... nicotinamide adenine dinucleotide? Everywhere I look ...
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106 views

Dehydration of carboxylic acids with phosphoric acid

To find Z one must find X. Finding Y is of no use to find Z. I get X as: After addition of $\ce{H2/Pd-C}$, the unsaturated portion becomes saturated and the carboxylic acid remains unchanged. ...
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61 views

The products of a chain reaction beginning with acetone and sodium amide

I encountered the following question in an exam: $\ce{CH3COCH3 + NaNH2}$  giving out $\ce{A}$. $\ce{A}$ then reacts with $\ce{C2H2}$ giving out $\ce{B}$. $\ce{B}$ then reacts with $\ce{H+}$ to ...
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Efficient way to synthesize poly(alkyl)amine

I am trying to synthesize poly(ethylene-propylene)amine, i.e.: I've read that Reductive Amination is efficient regarding the reaction yield. However, it needs aldehydes to start the reaction. To make ...
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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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200 views

Conversion of benzenediazonium chloride to benzene using lithium aluminium hydride

Why does benzenediazonium chloride get converted to benzene upon reacting with $\ce{H3PO2}$ and not $\ce{LiAlH4}$ ? Also, what is the reaction mechanism of the reaction with $\ce{H3PO2}$ ? This ...
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154 views

Preference for tin or iron in the reduction of nitrobenzene

My NCERT book(Class 12) said the following for reduction of nitrobenzene using $\ce{Sn/HCl}$ and $\ce{Fe/HCl}$ : Now, I have been following this mechanism for this particular reduction, and it seems ...
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614 views

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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Reduction with NH2-NH2 , OH-, and glycol

this question was asked in my exam and I have done it properly until the very third step but unfortunately, although the last step looked like wolfkishner reduction to me I could not do it. My ...
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29 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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250 views

What is the balanced equation of BH3/THF with an amide to form an amine? [closed]

I am doing a green chemistry project as an undergraduate and need the balanced equation to complete the calculations. I cannot find the right information online so any help would be greatly ...
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260 views

How does di-isobutylaluminium hydride ( DiBAl-H ) reduces carboxylic acid

$\text{DiBAl-H}$ reduces by electrophilic attack and provides hydrogen by $\text{H}^-$ transfer. Unlike $\text{LiAlH}_4$ it does not directly provide $\text{H}^-$ ion. So it should not undergo acid ...
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Will fruits and vegetables be more oxidized if blended at high speed for a long time or at less rpm for a short period of time? [closed]

Will fruits and vegetables be less oxidized if blended at higher speeds for shorter periods of time, or at lower speeds for longer periods of time? Do the oxidized molecules in vegetable juice ...
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Regarding Clemensen Reduction of the following compound [duplicate]

While I was doing problems on reduction of aldehydes and ketones, I encountered this particular question Here, I know that Clemensen reduction reduces the ketone group to $-CH_2-$ group. But, the ...
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278 views

Does sodium borohydride reduce C=N group?

Q.15 the major product of the following reaction is: I have read that $\ce{NaBH4}$ reduces only aldehyde, ketone and acid chlorides. In some cases it may reduce double bonds conjugated with ...
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43 views

6-oxoheptanal reaction with LiAlH4 [closed]

Is it possible? the reaction below
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39 views

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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123 views

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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152 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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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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326 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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248 views

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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81 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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118 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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391 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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178 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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146 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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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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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
341 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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446 views

Regioselectivity of epoxide hydrogenation using Pt versus Ni catalyst

What conditions are applicable for the transformations X and Y, respectively? (a) $\ce{LiAlH4}$, and $\ce{NaBH4}$ (b) $\ce{NaBH4}$, and $\ce{BCl3}$ followed by $\ce{NaBH4}$ (c) $\ce{LiAlH4}$, ...
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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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607 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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242 views

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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283 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
201 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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472 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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292 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
62 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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287 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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97 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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165 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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181 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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238 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?