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Unanswered Questions

1,538 questions with no upvoted or accepted answers
24 votes
0 answers
4k views

Do Cyclohexane-1,3-diones Give Positive Haloform Reactions?

Recently a post appeared on ChemSE asking why cyclohexane-1,3-dione (dihydroresorcinol) 1a doesn’t give a positive iodoform test. Unfortunately, the post was subsequently taken down after several ...
13 votes
1 answer
7k views

Why do alpha-hydroxy ketones respond positively to Tollens', Fehling's, Benedict's, Schiff's and HgCl2 tests?

I learnt from a certain textbook that aldehydes and formic acid respond positively to Tollens', Fehling's, Benedict's, Schiff's and HgCl2 tests. However, in another textbook I read that even alpha-...
10 votes
1 answer
328 views

Why are IUPAC's definitions of exo- and endothermic disconnected from the direction of heat flow?

I'm wondering if anyone can provide a rationale for IUPAC's definitions of exothermic and endothermic since they disconnect these terms from the direction of heat flow. Specifically, here are IUPAC's ...
10 votes
0 answers
20k views

Why does the reaction of sodium nitrate, aluminium, and sodium hydroxide yield ammonia?

From Russian test problem 4301: $$\ce{3NaNO3 + 8Al + 5NaOH + 18H2O -> 8Na[Al(OH)4] + 3NH3(g)}$$ How does ammonia evolve here? Is it that we get hydrogen gas evolving in the reaction between Al and ...
8 votes
0 answers
288 views

Alcohol to Ketone by CrO3 in cyclohexane

I have encountered an exercise question on conformation of cyclohexane and there is a statement saying, 'converting alcohol to ketone by CrO3 is much faster when R-OH is in axial position'. I would ...
8 votes
1 answer
2k views

Do all α-hydroxy ketones give Tollens’ test?

It is well known that terminal α-hydroxy ketones give Tollens’ test, via tautomerisation. Also, α-hydroxy ketones flanked by aromatic groups give Tollens’ test, such as benzoin. But do all α-hydroxy ...
8 votes
0 answers
392 views

What exactly is an "electron-sponge"?

What exactly an "electron-sponge" [behavior/action/property/system] nickname is, and what makes a material an "electron-sponge" (preferably, quantitatively)? From what I found, it's typically a ...
8 votes
0 answers
102 views

Removal of nickel plating on MgB2 without damaging the boride?

I need to remove a nickel plating of a MgB2 wire without causing damage to the MgB2. I felt that electrolysis is the best method but I do not know what electrolyte to use for this. I also need to coat ...
8 votes
0 answers
426 views

Grubbs, Wittig & hydroboration reactions and Woodward-Hoffmann rules

Several organic mechanisms I know involve [2+2] cycloadditions and retro-[2+2] cycloadditions, namely: The Wittig reaction Hydroboration of an alkene Olefin metathesis (using Grubbs' catalyst) How ...
7 votes
0 answers
183 views

Why does entropy increase in reactions that make more molecules?

I used to understand this (more molecules ⇒ more degrees of freedom), but do no longer, because the total number of atoms is conserved, so translational d.o.f. should just be turned into internal d.o....
7 votes
0 answers
1k views

Textbook suggests secondary alkyl halides do not undergo SN1 reaction

The 8th edition of Organic Chemistry by Paula Bruice suggests that secondary alkyl halides do not undergo SN2 reactions. However, many other sources state the opposite. So, what is the correct answer? ...
7 votes
0 answers
516 views

Does phosphoric acid remove stainless steel electropolished layer?

Electropolished stainless steel has a high corrosion resistance due to the oxide film that is created during electropolishing. The film mainly consist of chromium(III) oxide. Phosphoric acid is ...
7 votes
0 answers
239 views

Solve this chemical or biological mystery

I hope this is the best place to pose this unique question. Please forgive me if it's not. I went into a closet to get a prescription medication that was filled about a year ago. The label on the ...
7 votes
1 answer
5k views

Orientation in benzene rings with more than one substituent

Why is it that the chlorination of 1-chloro-3-nitrobenzene (18) gives 1,4-dichloro-2-nitrobenzene (19) as the major product, 1,2-dichloro-3-nitrobenzene (20) as a minor product and 1,2-dichloro-4-...
6 votes
0 answers
246 views

How to determine the surface reaction rate and equilibrium constant for a reaction between a solid site species and gas species

Consider the following reaction mechanism 1: S1: $\ce{C-H (s) + H (g) <=> C^\star (s) + H2 (g)}$ S2: $\ce{C^\star (s) + H (g) => C-H (s)}$ S3: $\ce{C^\star (s) + C2H2 (g) => C-H (s) + H(g) ...

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