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.

Filter by
Sorted by
Tagged with
2
votes
1answer
365 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 ...
1
vote
0answers
246 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)?
0
votes
1answer
238 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 ...
1
vote
0answers
96 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 ...
4
votes
1answer
598 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
votes
1answer
568 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) $\ce{LiAlH4}$, ...
0
votes
0answers
258 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 ...
1
vote
1answer
1k 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?
-2
votes
1answer
474 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
votes
1answer
632 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 ...
2
votes
2answers
256 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
votes
1answer
982 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 ...
0
votes
0answers
25 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 ...
-1
votes
2answers
75 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.
1
vote
0answers
511 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)
1
vote
1answer
109 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. ...
2
votes
2answers
286 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. ...
6
votes
1answer
232 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 ...
-2
votes
1answer
383 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?
1
vote
0answers
56 views

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 ...
2
votes
1answer
179 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 ...
-1
votes
1answer
1k 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
2
votes
0answers
238 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 ...
1
vote
2answers
437 views

What will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride?

What will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride? I feel the answer should be 2-(2-hydroxypropyl)cyclohexan-1-one: Because the carbonyl carbon on the aliphatic ...
2
votes
1answer
632 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 $\...
5
votes
1answer
675 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) ...
11
votes
1answer
2k 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 ...
5
votes
1answer
3k 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 ...
-1
votes
1answer
72 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 ...
1
vote
0answers
76 views

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 $\ce {H_2}$?
1
vote
1answer
481 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.
6
votes
3answers
8k views

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 ...
7
votes
1answer
9k views

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 ...
5
votes
1answer
438 views

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 ...
6
votes
1answer
6k views

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 ...
4
votes
1answer
5k views

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 ...
6
votes
1answer
2k 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 ...
5
votes
3answers
547 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. ...
10
votes
1answer
11k views

Why does LiAlH4 reduce an amide to an amine, but only reduce a ketone/aldehyde to an alcohol?

Here are two different reactions in which lithium aluminium hydride, $\ce{LiAlH4}$, reduces a carbonyl group: Why does $\ce{LiAlH4}$ completely remove the oxygen from the amide, but only reduces the ...
1
vote
1answer
247 views

Stabilization of ipso and para position in Birch reduction by EWG of aromatic ring

I'm trying to grasp the Birch reduction. In the lecture about it, it's said that the EWG group stabilizes ipso and para position through resonance. I tried to understand that by drawing resonances ...
14
votes
2answers
12k views

Reduction of glucose to hexane with hydroiodic acid

My book (NCERT India) states that n-hexane is formed when glucose is heated in the presence of hydrogen iodide. That is, the following reaction takes place: $$\ce{C6H12O6 + HI ->[{\Delta}] C6H14}$$ ...
4
votes
2answers
2k views

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 ...
5
votes
1answer
6k views

Chemoselectivity in reduction of 3′-nitroacetophenone

When 3′-nitroacetophenone is treated with sodium borohydride, only the carbonyl group is reduced (top); however, when reacted with tin and hydrochloric acid only the nitro group is reduced (bottom). ...
0
votes
1answer
103 views

Stereo selective reaction products

Pyruvic acid on reduction with yeast gives (-) lactic acid while with $\ce{NaBH4}$ it reduces to (+) lactic acid. How? I know this has something to do with stereoselectivity. But I don't know which ...
6
votes
1answer
25k views

Color of precipitate formed on reaction of acetylene with Tollen's Reagent

I am asked to find the color of the precipitate formed by the passage of acetylene gas into an aqueous solution of ammoniacal silver nitrate. I thought ammoniacal silver nitrate was Tollen's reagent,...
4
votes
0answers
213 views

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 ...
8
votes
2answers
2k views

How can an aromatic ketone be reduced in the presence of a nitro group?

Is it possible to reduce an acyl group to an alkane, but still keep a nitro group intact without its reduction to an amino group? A Clemmensen reduction would reduce the nitro group, and it seems like ...
6
votes
1answer
8k views

How to convert benzamide to benzylamine?

Question Benzamide can be converted to benzylamine using A) $\ce{Br2,\ KOH}$ B) $\ce{PCl5}$ C) $\ce{LiAlH4}$ D) $\ce{NaBH4}$ My answer: Reducing agent is used so C and D ...
8
votes
2answers
13k views

Reactions of alkynes with sodium/ammonia vs sodium amide

What happens when alkynes react with sodium in ammonia ($\ce{Na/NH3}$), or when they react with sodium amide ($\ce{NaNH2}$)? Are these two sets of conditions different?
6
votes
1answer
7k views

What is the purpose of ammonium chloride in anti hydrogenation of alkynes?

In my organic chemistry textbook, lithium is used to create a free radical of the alkynes, to then allow the anti addition of hydrogen to get an alkene. "The Dissolving Metal Reduction of Alkynes" is ...