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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186 views

Reduction of carbamate with LAH

The products of the reduction of esters with $\ce {LiAlH4}$ and the products of the reduction of amides with $\ce {LiAlH4}$ are vastly different. The former reduction cleaves the ester and produces ...
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0answers
23 views

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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25 views

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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1answer
49 views

Diborane reduction

I am stuck at a step in reduction of alkene using $\ce{B2H6}.$ I assume that step 1 is the addition of borane to alkene. After that a water molecule attacks $\ce{-BH2},$ it being a Lewis acid. ...
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1answer
29 views

Which of these reactants will not generate this racemic amine?

I understand that in E there is no electrophile the amine can attack, however, I do not understand why A is an answer as well. The amine in A can perform an intramolecular attack on the aldehyde and ...
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2answers
94 views

Chemical Reaction Alternative to O2 Respiration in H2/N2 Atmosphere [closed]

Note: If this question does not belong on this Stack Exchange, please direct me to a more appropriate Stack Exchange. This is a "creative chemistry" question as much or more-so than a "give me the ...
1
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1answer
42 views

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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0answers
53 views

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 ...
2
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1answer
114 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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0answers
35 views

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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15 views

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 ...
3
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1answer
37 views

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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1answer
197 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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1answer
95 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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1answer
38 views

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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0answers
20 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 ...
6
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1answer
293 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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0answers
287 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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1answer
1k 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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1answer
132 views

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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0answers
33 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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1answer
463 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 ...
2
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2answers
459 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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1answer
43 views

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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0answers
39 views

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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1answer
356 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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1answer
60 views

6-oxoheptanal reaction with LiAlH4 [closed]

Is it possible? the reaction below
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0answers
40 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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1answer
156 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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1answer
208 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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1answer
29 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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1answer
589 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....
4
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0answers
309 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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1answer
100 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 ...
2
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0answers
131 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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1answer
486 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? ...
2
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1answer
231 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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0answers
182 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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1answer
164 views

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
83 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 ...
3
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1answer
408 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 ...
20
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1answer
494 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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0answers
115 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
746 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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1answer
321 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 ...
2
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1answer
353 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
217 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 ...
2
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1answer
636 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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0answers
24 views

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
63 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.