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For questions about reduction reactions in organic chemistry, where a molecule of interest is reduced. Do not use for questions on general redox concepts.

2
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1answer
43 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 ...
16
votes
1answer
260 views
+50

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 ...
0
votes
0answers
29 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
62 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
46 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
75 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 ...
1
vote
2answers
111 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
71 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
49 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 ...
0
votes
0answers
22 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
49 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
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0answers
33 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
78 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
61 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
98 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 ...
-1
votes
1answer
114 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?
0
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0answers
38 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
60 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
202 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
59 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
115 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 ...
1
vote
1answer
179 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 $\...
0
votes
0answers
223 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{...
4
votes
1answer
124 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) ...
7
votes
0answers
293 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 ...
2
votes
1answer
225 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
49 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
45 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
113 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.
2
votes
1answer
1k 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 ...
2
votes
0answers
2k 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 ...
3
votes
1answer
114 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 ...
3
votes
2answers
1k 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 ...
5
votes
1answer
398 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 ...
8
votes
1answer
5k 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
175 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 ...
8
votes
0answers
6k views

Reaction of glucose with hydroiodic acid

My book (NCERT India) states that n-hexane is formed when glucose is heated in presence of hydrogen iodide. That is, the following reaction takes place: $$\ce{C6(H2O)6 + HI ->[{\Delta}]C6H14}$$ ...
4
votes
2answers
919 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 ...
0
votes
1answer
84 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 ...
5
votes
1answer
14k 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,...
8
votes
2answers
1k 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
5k 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 ...
4
votes
1answer
5k 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 ...
12
votes
2answers
42k views

Nitrobenzene reduction with (tin) Sn catalyst: Why is C-H bond cleavage preferred over O-H bond cleavage?

I am trying to understand this mechanism for nitrobenzene reduction with $\ce{Sn/HCl}$. I do not understand why it implies that you pull off the $\ce{C-H}$ hydrogen instead of the $\ce{O-H}$ hydrogen ...
6
votes
1answer
8k views

Reaction mechanism for reduction of nitrobenzene to aniline in catalytic and acidic media

Can anyone explain the reaction mechanism of the two reactions given below? They are the conversion of nitrobenzene to aniline in catalytic ($\ce{H2/Pd}$ in ethanol) and acidic ($\ce{Sn/HCl}$ or $\ce{...
8
votes
1answer
28k views

Why does NaBH4 reduce double bonds conjugated to carbonyl groups, while LiAlH4 does not?

I have been going through reduction of aldehydes using $\ce{LiAlH4}$ and $\ce{NaBH4}$. If there is a double bond conjugated with the carbonyl group, $\ce{LiAlH4}$ doesn't reduce it, leading to an ...
2
votes
1answer
188 views

Products for the hydrogenation of the cycloalkene in (3R,4R,5S)-4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid

Write the products (more than one) for the hydrogenation of the cycloalkene ring in (3⁠R,4⁠R,5⁠S)-4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid. Reagents are molecular hydrogen with ...