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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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2 answers
8k views

What are acid/base sensitive groups?

My textbook says that Clemmensen Reduction cannot take place in the presence of an acid-sensitive group and the Wolf Kishner reaction won't happen in the presence of a base sensitive group, citing $\...
0 votes
1 answer
170 views

In what cases can LiAlH4 reduce alkene, or alkyne?

Lithium aluminium hydride $(\ce{LiAlH4})$ is known for its vast usability as reducing agent since it can reduce almost any organic functional group to alcohols, amines etc. Despite being so versatile, ...
0 votes
1 answer
88 views

What is the full mechanism for the controlled reduction of an alkyne using LiAlH₄?

Was going through my notes and realised I didn't completely fill them in. The first few steps I think are quite self-explanatory but I'm really confused about the last step where I go from the five-...
9 votes
2 answers
21k 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
1 answer
86 views

Why do halobenzenes not give Birch reduction?

I was studying Birch reduction and my book says halobenzene and phenol do not give Birch reduction. I want to know why these two type of compounds do not give Birch reduction. I also want to know if ...
3 votes
1 answer
336 views

Converting cyclic compounds to their corresponding aliphatic compounds

Is there any reaction available to convert cyclic compounds to their corresponding aliphatic compounds? eg. Converting cyclohexane to n hexane
-4 votes
2 answers
1k views

Does H2, Pd/C reduce a conjugated ketone?

Would H2, Pd/C be a sufficient reagent for this reaction to proceed? The question is from a test which asked what would be the most suitable reagent for the above reaction
12 votes
1 answer
9k views

How is NaBH4 able to reduce tertiary alkyl halides to alkane but LiAlH4 create an alkene?

When attacking tertiary alkyl halides, aren't both of them just supposed to follow $\mathrm{S_N2}$ and substitute the leaving group with Hydride ion? Apparently only $\ce{NaBH4}$ does it and $\ce{...
3 votes
0 answers
51 views

Why doesn't β-elimination occur in Cr(CMe3)4?

By $\beta$-elimination, I am refering to the reaction where a M-C-C-H structure reduces to ($\eta^2$-alkene)-M-H. My lecture notes claim that $\ce{Cr(CMe3)4}$ is stable and does not incur such ...
1 vote
2 answers
3k 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 ...
5 votes
0 answers
130 views

Electrolytic reduction of nitrobenzene in differing media

In my lecture notes it is given that in a weakly acidic medium, nitrobenzene on electrolytic reduction gives aniline, which makes sense to me because there is ample H+ in the medium to continue adding ...
13 votes
2 answers
2k 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 ...
0 votes
0 answers
45 views

How does the Eschweiler Clarke reaction occur with sodium cyanoborohydride as a reducing agent?

I am specifically confused with 2 concepts. How sodium cyanoborohydride acts as a reducing agent. I read that it acts as a source of hydride but I am not sure how this works. If anything, I assumed ...
0 votes
0 answers
83 views

Reagent for conversion of 1-phenylpent-1-en-3-one to 1-phenylpent-1-en-3-ol

This conversion was recently asked in the NSEC, an Indian (preliminary) chemistry olympiad for high schoolers and the official answer key stated LiAlH4 is the correct reagent to be used. However I ...
0 votes
0 answers
40 views

Is this mechanism of reduction using LiAlH4 followed by hydrolysis of an amide correct?

Hello everyone. I had been given a question on reducing an amide group into an amine group using any reagent I saw fit as homework. I had used LiAlH4, which provides H- and does an acid base reaction ...
2 votes
0 answers
80 views

What is the product and mechanism of reducing a cyclohexanone derrivative with LAH?

I've been trying to figure out the product and mechanism of the reaction pictured below for a while now: I'm fairly sure that the first step is the reduction of the ketone by LAH, which results in a ...
4 votes
1 answer
7k 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. ...
6 votes
1 answer
1k views

Reduction of amino acids to corresponding amino alcohols

I've stumbled upon an interesting article about reduction of amino acids and from there to reduction of L-valine to L-valinol using $\ce{LiAlH4}$ in THF. Article says that because of the cost of $\...
3 votes
1 answer
97 views

Reduction of di-N-substituted imidazole to imidazoline to remove counterion?

I would like to synthesize a di-N-substituted imidazole (compound 4) in its free base form or reduce it to generate an imidazoline (compound 5) to remove the bromide counterion to the imidazole ring. ...
2 votes
0 answers
84 views

Reduction of benzylic alcohol and halide using H2 and Pd

I am studying drug synthesis, and I found some examples that uses $\ce{H_2}$ and Pd/C or Pd/$\ce{BaSO_4}$ as catalytic hydrogenation reagents for reduction of alcohol or halide in benzylic position. ...
2 votes
1 answer
3k 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
2 answers
420 views

What determines the location of nucleophilic attack on a conjugated ketone or aldehyde?

In a conjugated ketone or aldehyde, nucleophiles could attack the double bond or the carbonyl carbon. I have two examples that differ in the location of initial attack, and I am wondering what ...
4 votes
2 answers
759 views

Partial reduction of anthraquinone to anthrone using stannous chloride?

I've heard of using $\ce{SnCl2}$ in the Stephen's reaction where you reduce a nitrile down to an aldehyde. I've come across a laboratory manual that discusses using tin in the partial reduction of ...
1 vote
0 answers
63 views

How do I make this terminal alkyne into a methyl alkene on the third carbon?

How do I get from but-3-yn-1-ylbenzene to (3-methylbut-3-en-1-yl)benzene? I have tried $\ce{NaNH2}$ in $\ce{CH3Br}$ and then $\ce{H2}$ with a Lindlar catalyst, but that adds the methyl group at the ...
-1 votes
1 answer
96 views

How can I protect the ester group from reduction? [closed]

If I process this reaction the NaBH4 will also reduced the ester group to alcohol. I want to convert the Nitro (-NO2) functional group to Amine (-NH2) without disturbing the Ester group. So, my ...
3 votes
1 answer
7k 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 ...
3 votes
1 answer
176 views

Conditions for Pd/C reduction of alkene

I am trying to do a $\ce{H2}$ reduction of cyclic alkene (otherwise simple hydrocarbon with 1 methyl group along with the chain about the weakly-strained cycle) using $\ce{Pd/C}$, the cycloalkene ...
2 votes
1 answer
2k views

Why does DIBAL-H not reduce esters to alcohols directly?

This source says that DIBAL-H reduces esters to aldehydes. Further, it says that, like NaBH4, it reduces aldehydes too. Why in reduction of ester, the aldehyde so formed is not converted to alcohol, ...
16 votes
1 answer
17k 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 ...
7 votes
2 answers
453 views

What is the major product in the reaction between 4-chloropentanal and lithium aluminium hydride?

What would be the major product between 4-chloropentanal and $\ce{LiAlH4}$? After the reduction of the aldehyde, would the hydroxyl group formed at $\ce{C-1}$ attack $\ce{C-4}$ causing cyclization to ...
0 votes
0 answers
477 views

What is the effect of NaNO2/HCl at 0-5° C on Nitro group?

In this particular reaction firstly $\ce{NaNO2/HCl}$ at $\pu{0-5°C}$ was taken and after that $\ce{H2/Ni}$ . But what I doubt is, was there any role of $\ce{NaNO2/HCl}$ at $\pu{0-5°C}$ ? Since only ...
-2 votes
1 answer
1k views

Does sodium borohydride reduces alkyne? [closed]

Will an isolated Alkyne or an alkene be reduced using sodium borohydride ($\ce{NaBH4}$)?
2 votes
0 answers
118 views

Red P+HI with some specific functional groups

I've seen the related question (Does RedP+HI reduce all carbon functional groups to alkane?). Although the question is admittedly similar, neither the answer provided nor the document linked in it ...
1 vote
0 answers
96 views

Rearrangement vs. Ring Strain in Cyclobutanecarboxaldehyde Nucleophilic Reaction

Predict the major product of the following reaction: Note: Product A is incorrectly marked as secondary halide, it should have been primary halide This question appeared in an national level ...
1 vote
1 answer
401 views

Reduction of unsymmetrical ketones using BINAL-H (Enantioselectivity)

I am struggling with a problem regarding the enantioselectivity of BINAL-H for quite some time now. The reaction scheme shows the reaction with (S)-BINAL-H as it is observed plus the transition state ...
0 votes
0 answers
386 views

Why isn't the Leuckart reaction used to make (meth)amphetamine?

For example, in Breaking Bad, they synthesize meth from phenylacetone. Why not just use methylammonium formate, if they already have methylamine?
6 votes
0 answers
280 views

Reactivity order of DIBAL-H and diborane with esters and acids

I have been taught in class that DIBAL-H is more reactive towards esters than carboxylic acids while opposite is true for diborane. Also DIBAL-H mentioned is taken under low temperatures (−78 °C). I ...
3 votes
1 answer
2k views

Acid hydrolysis of Birch-reduced Anisole

The following is a question from Advanced problems in organic chemistry by MS Chouhan: Product $A$ is rather straightforward: and on acidic hydrolysis, the following reaction takes place: Here the ...
1 vote
0 answers
58 views

Chlorinated hydrocarbon destruction

What's a convenient method for lab-scale destruction of chlorinated hydrocarbons? Reductive dechlorination, total oxidation are fine as well as other routes you want to point out. If specific ...
0 votes
1 answer
2k views

Why adding sodium bicarbonate quenches a reductive amination using sodium triacetoxyborohydride?

I'm planning to do a reductive amination reaction between methyl pyruvate and benzylamine using sodium triacetoxyborohydride, $\ce{NaBH(OAc)3}.$ Acetic acid is used as a catalyst for protonating the ...
5 votes
3 answers
4k views

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

I would like to know if there is a possible route of synthesis that may reduce 3-nitrobenzonitrile A to 3-aminobenzonitrile B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
3 votes
1 answer
497 views

Why does BH3/THF reduce the carbonyl group to a methylene rather than an alcohol?

This reaction is taken from: Pintér, Á.; Sud, A.; Sureshkumar, D.; Klussmann, M. Autoxidative Carbon-Carbon Bond Formation from Carbon-Hydrogen Bonds. Angew. Chem., Int. Ed. 2010, 49 (29), 5004–5007. ...
3 votes
1 answer
643 views

Does red phosphorus with hydriodic acid reduce all alkyl halides?

$\ce{HI/P}$ is used for reduction of alcohols, aldehydes, ketones and acids to alkanes. As for alkyl halides, I have read that only alkyl iodides are reduced, whereas other alkyl halides do not: $$\ce{...
2 votes
0 answers
112 views

Reduction of orthoesters and acetals with LiAlH4

As I know, orthoesters react with $\ce{LiAlH4}$. After searching on the Internet I’ve found that acetals react with $\ce{LiAlH4}$ in the presence of $\ce{AlCl3}$. Why can’t acetals be reduced only in ...
2 votes
0 answers
51 views

Naftiridine hydrogenation

I was reading an article about the synthesis of 1,2,3,4 tetrahydronaphtyridine and I found this image. I don't understand why the major product of hydrogenation is the less substituted and not the ...
8 votes
1 answer
4k views

Why does Birch reduction of naphthalene with isoamyl alcohol form tetralin instead of 1,4-dihydrodialin (as formed with C2H5OH)?

I recently came across this question, which required me to know the difference between performing a Birch reduction on naphthalene using ethanol and using isopentanol. Why does using isopentanol lead ...
-1 votes
2 answers
257 views

Reaction mechanism of phenylhydrazine with carbonyl

I am currently working on the following problem, but I don’t know how it is solved: I guess it is a Fischer-Indol synthesis, but I am not sure. This is what I got: Any help would really be ...
0 votes
0 answers
209 views

How does deprotonation works?

I've been studying organic chemistry and came across this example : CH3-CH2-CH(+)-CH3 ---> CH3-CH=CH-CH3, the explanation the textbook gave was related to deprotonation. I've tried drawing lewis ...
-1 votes
1 answer
43 views

Where does Aluminum Hydroxide come from in a reduction of a ketone by LAH? [closed]

The experiment was done in a Laboratory. A ketone was reduced with LAH in THF under reflux. At the end of the reaction, the protocol stated to add water until there is no more H2 released. The H2 ...
1 vote
0 answers
368 views

Selective reduction of aromatic nitro group

In the following compound, is it possible to selectively reduce the aromatic nitro group to an amine, as shown in the reaction? I fear that the methods usually used to reduce aromatic nitro compounds,...