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Questions tagged [stereochemistry]

Applicable to questions about the spatial arrangement of atoms in a molecule and how they affect its physical or chemical properties.

6 votes
2 answers
2k views

How can a molecule with a double bond on one side have a plane of symmetry, and thus, be achiral?

Does norbornene have a plane of symmetry? Is norbornene achiral or chiral? I think norbornene is chiral since there is a double bond on the only one side. Thus, there is no plane of symmetry. The ...
songgio123's user avatar
4 votes
1 answer
687 views

Why does 2,3 dichlorobutane have 2, and not 3, stereoisomers

I understand how and that the R,S and R,R stereoisomers are different. But I don’t see why the R,R and S,S compounds are stereoisomers and not meso compounds with each other. Online it says that ...
Kirandk's user avatar
  • 422
1 vote
1 answer
285 views

Converting structures into Fisher projections

I am really struggling with converting pyrano/furanosides into their Fisher projection counterparts. Especially when they are drawn like in the shown projection. When do you know to connect the ...
Abigail's user avatar
  • 11
1 vote
1 answer
79 views

Are substituents placed alphabetically in the name of a cycloalkane?

I named this molecule 1,5-diethyl-2-methyl-4-propylcyclohexane. Is this correct? Or should we somehow use the size of the substituents?
TNF's user avatar
  • 39
0 votes
2 answers
298 views

Is eta hexachloro cyclohexane optically active compound?

Quoting from Wikipedia, Hexachlorocyclohexane (HCH), $\ce{C6H6Cl6}$, is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to ...
Infinite's user avatar
  • 1,644
0 votes
0 answers
353 views

How to determine if the ring compound has optical isomers?

The first column and fourth column of the table below says that the compound has the plane of symmetry and is not optically active. However, I noticed that each side has different arrangement of the H ...
L.P.'s user avatar
  • 1
1 vote
1 answer
160 views

How to depict small molecules such as D-glucose based on isomeric SMILES

The isomeric SMILES for D-glucose is C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O. The Haworth projection looks like this: I can parse the SMILES and draw the ...
david.pfx's user avatar
  • 111
0 votes
0 answers
112 views

How does bis(glycinato) Nickle exhibit optical isomerism?

I'm a medical practitioner but sometimes I find time to discuss few topics of chemistry with my son who has just passed out his 12th standard exams. Regarding optical isomerism I have learned that a ...
Jagbir Singh Kanet's user avatar
6 votes
2 answers
2k views

Why are the products of Grignard reaction on an alpha-chiral ketone diastereomers rather than a racemate?

Comment on stereochemistry of products. This is a Grignard reaction and the product has two chiral carbons. I think it should be a racemic mixture. However, my teacher says the correct answer is ...
Arpit Raj Choudhary's user avatar
2 votes
0 answers
132 views

stable conformation of 2,3-dimethylsuccinic acid

I was researching for answering this question on Kolbe's electrolysis of 2,3-butanedicarboxylic acid (succinic acid). Turns out, this compound is not very well researched in particular, and shows few ...
ananta's user avatar
  • 2,304
2 votes
0 answers
640 views

Is hydroxylamine monodentate or ambidentate ligand?

What is the total number of geometric isomers of the complex $\ce{[Pt(Cl)(py)(NH3)(NH2OH)]+}$? If $\ce{NH2OH}$ acts as an ambidentate ligand, then there should be six geometric isomers. Or is it ...
Ritesh 's user avatar
-1 votes
1 answer
312 views

Does no optical rotation always implies optical inactivity? [duplicate]

This question popped up in my mind in reference to this question, Is a compound optically active if plane polarised light is deflected by an angle of n*(2π) angles? Suppose that I give a chemistry ...
Ritil's user avatar
  • 340
-1 votes
1 answer
80 views

Is a compound optically active if plane polarised light is deflected by an angle of n*(2π) angles? [closed]

Is a compound optically active if plane polarised light is deflected by an angle of n*(2π) angles(like 360°); as there won't be any deflection in the analyser of the polarimeter?
An_Elephant's user avatar
1 vote
1 answer
472 views

Does the 3D structure generated with MolView violate the wedge-dash rules of "above/below the plane"?

I've been taught that in a wedge-dash diagram, the wedge represents a bond above the plane of the paper, and the dash represents a bond below the plane. Accordingly, I expected the structure of this ...
Righter's user avatar
  • 304
2 votes
3 answers
3k views

Why is diequatorial trans-1,2-dimethylcyclohexane more stable than diaxial trans-1,2-dimethylcyclohexane?

Consider diequatorial trans-1,2-dimethylcyclohexane and diaxial trans-1,2-dimethylcyclohexane as shown in the figure below [1, p. 178]. In both compounds, the ring is free of angle strain. trans-1,2-...
An_Elephant's user avatar

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