Stack Exchange Network

Stack Exchange network consists of 175 Q&A communities including Stack Overflow, the largest, most trusted online community for developers to learn, share their knowledge, and build their careers.

Visit Stack Exchange

Questions tagged [stereochemistry]

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

3
votes
1answer
28 views

Creating a Battery using azobenzene in High School [on hold]

I’m doing a project on isomerization in high school and have stumbled across the studies involving azobenzene in energy storage using its photoisomeric properties and sunlight . Do you think that this ...
-4
votes
0answers
17 views
4
votes
2answers
50 views

Which one has higher priority according to Cahn–Ingold–Prelog rules?

Which one has higher priority according to Cahn–Ingold–Prelog rules? (1) $\ce{-CH2OH}$ and $\ce{-CH=CH2}$ (2) $\ce{-CH2OH}$ and $\ce{-C(CH3)3}$ The answer says $\ce{-CH=CH2}$ has higher ...
1
vote
1answer
70 views

What is the correct number of stereo isomers in case of 3,6-dimethylpiperazine-2,5-dione?

What is the correct number of stereo isomers in case of the following compound, i.e. 3,6-dimethylpiperazine-2,5-dione? The answer key gives three, but I think there should be four. I recognised the ...
-1
votes
1answer
54 views

Predict stereochemistry of product [closed]

When 3-methyl(1,1-2H2)pent-1-ene reacts with HCl, why do we obtain a racemic mixture? The given reactant is optically pure.
1
vote
1answer
141 views

Are all alkene geometrical isomers achiral?

I was reading a book and it tells that alkene geometrical isomers are achiral. I wanted to know that is it applicable for alkene geometrical isomers? Thanks in advance.
0
votes
1answer
45 views

What do D and L stand for in the Fischer-Rosanoff convention?

In R and S configuration, the R stands for rectus and the S stands for sinister. Similarly, do the D and L descriptors in the Fischer-Rosanoff convention stand for something?
1
vote
1answer
99 views

number of optical isomers of a cyclic molecule

What is the number of optical isomers for this compound? Also, there seems to be no clear-cut boundary between geometrical isomers and optical isomers. Referring to a post in StackExchange, is (RS)- ...
1
vote
0answers
42 views

Number of products on dehydrobromination

Question: The total number of alkene products possible from the dehydrobromination of 3-bromo-3-cyclopentylhexane using alcohol KOH is : This question was asked here before but I am getting more ...
2
votes
1answer
54 views

Depicting molecules by Natta projection

Does anyone know the meaning of these two bonds in stereochemistry? These bonds are provided by the $\mathrm{\LaTeX}$ chemfig package. The creator of the ...
0
votes
1answer
75 views

Can anyone tell me what reaction is this?

I came across this reaction, but I have no idea what reaction is this. Can anyone please tell me? What will be the products? My first guess is that a carbene will be formed which will attack on the ...
0
votes
1answer
61 views

Total number of stereoisomers of 1,2-dimethyl-4-(propan-2-ylidene)cyclopentane [duplicate]

I don't think there is any change of showing geometrical isomerism across the double bond because the two groups on the right side (two $\ce{-CH_3}$) are the same. Also I don't think there should be ...
3
votes
1answer
94 views

How many stereoisomers are possible for 1,2-dimethyl-4-(propan-2-ylidene)cyclopentane?

How many stereoisomers (not counting different conformers) does 1,2-dimethyl-4-(propan-2-ylidene)cyclopentane have? I think the answer should be 3. There are two geometrical isomers (cis and ...
1
vote
0answers
29 views

Diels Alder stereoselectivity

I'm familiar with the endo rule as well as the regioselectivity of the reaction. However, what I fail to understand is the stereoselectivity of the product in relation to the diene. For example, in ...
-1
votes
1answer
39 views

Optical activity of organic compunds

Why are the molecules which are superimposable on their mirror images optically inactive? For example 1-bromo-2-methylpropane.
0
votes
4answers
75 views

Total number of stereoisomers of 2,3,5,6-tetrachlorooctane

I tried the following combinations: RRRR, SSSS, RRRS, SSSR, RRSS, RSRS, SRRS, RSSR, RSRR, SRSS, RRSR, SSRS, SSRR, SRSR. So total stereoisomers which I got is 12 but my teacher says it's 16. I don't ...
4
votes
0answers
42 views

Endo/Exo for same length bridges

I'm looking at a cycloaddition that produces a bicyclic intermediate, there are two different ways of doing the addition which can be described as endo/exo. However, all three bridges are the same ...
1
vote
0answers
36 views

Enantioselective alkylation of Aldehydes by Dialkylzinc reagents

Enantioselective catalysis is one of the important reactions in Organic chemistry which has huge applications in practical basis for synthesis of optically pure natural compounds. In this respect, I ...
4
votes
1answer
82 views

Optical Isomerism in Coordination Compounds of type MA₂B₂(CC)

I was asked the following question: How many optical isomers are there for $\ce{[Cr(NH3)2Cl2(en)]^+}$ ? First of all I figured out the following four geometrical isomers of the above complex: Out ...
-1
votes
2answers
43 views

Is there absolotely no relation between R/S configurations and d/l optical rotations?

Is there such a relation between R/S configurations and d/l optical rotation that, if we experimentally know that R configuration of a fixed compound gives 'l' rotation then can we infer that the S ...
-1
votes
1answer
33 views

Enantiomers and couple of enantiomers

I ask myself a question for some time but it's impossible to me to find the answer! I can't understand the difference when we say " that molecule has a enantiomer " and when we say " has a couple of ...
3
votes
0answers
141 views

X-ray structure analysis mirrored coordinates?

How to ensure, that X-ray crystallography structure analysis was done right to provide correct, non-mirrored atomic coordinates? Example: Following Wikipedia image, is generated from data taken from ...
4
votes
3answers
126 views

Is there a thermodynamic driving force for racemisation?

Why does racemisation occur? My doubts are: Is it due to entropy? If it is due to entropy, how is the reduction of optical activity by racemisation a consequence of increased thermodynamic ...
0
votes
1answer
34 views

What is the configuration of dimethyl[tris(trifluoromethyl)]-λ⁵-phosphane?

I know that $\ce{(CH3)2P(CF3)3}$ is geometry of trigonal bipyramid and according to Bent's rule $\ce{CH3}$ goes to axial positions and $\ce{CF3}$s remains on equatorial positions. However, as per ...
4
votes
2answers
101 views

Does 3,6-di-X-cyclohexa-1,4-diene have stereo centers?

The following question has multiple correct answers: The book out of which the question is taken shows that a, b and d are correct answers. According to me c should also be correct, as it shows ...
1
vote
2answers
42 views

Are the stereoisomers of nucleosides actually anomers?

An anomer is an epimer at an (hemi)-acetal carbon like $\ce{R2C(OR')2}$. Why is the 1'-position of a nucleoside referred to as the anomeric center despite the lack of acetal functional groups?
0
votes
1answer
40 views

According to the Cahn-Ingold-Prelog system assign a priority to each of the following groups. (Highest priority is 1) [closed]

1-CH(CH3)CH2F 2-CHCl2 3-CH2Br 4-C(CH3)3 this is the order i did using the system but i am having a hard time understanding it and was wondering if anyone could tell me if my answer is correct, and if ...
1
vote
1answer
92 views

Classification in Stereoisomerism [closed]

I was trying to understand stereoisomerism. I am having trouble creating a 'flow chart' of Stereoisomerism. While there are many sources available over the internet and books, I don't find a standard ...
5
votes
0answers
89 views

What compound has the strongest optical rotation of polarised light?

A question recently asked here whether compounds know to be chiral can have non-measurable optical rotations: Are there chiral compounds that don't rotate plane-polarized light?. Apparently they ...
6
votes
1answer
462 views

Are there chiral compounds that don't rotate plane-polarized light?

I know that meso compounds have chiral centers but don't rotate plane-polarized light, and I know that there can be non-traditionally chiral compounds (e.g. ones with large substituents that prohibit ...
3
votes
1answer
58 views

Assign stereodiscriptor to 4th carbon of 3-ethyl-2,4-dimethly-5-(propan-2-yl)heptane-1,7-diol

Here is the molecule. Clearly the 4th carbon is chiral. I have drawn the diagraph for it, but the exploratory pathways of the left and right chains are the same. So, the problem is that the two chains ...
0
votes
2answers
181 views

Why does 1,3-dichloropropane not show stereoisomerism?

It is a multiple choice question: Which compound does not show stereoisomerism? A 1,2-dichloroprop-1-ene B 1,2-dichloropropane C 1,3-dichloroprop-1-ene D 1,3-dichloropropane I ...
-1
votes
1answer
300 views

Determining R and S configuration for a cyclic compound when the lowest priority group is on the plane of the paper

I am struggling with determining R and S configuration for the following compound I know how to give R and S configuration for a cyclic compound like the compound above if the lowest priority group ...
0
votes
2answers
178 views

What is the most stable conformation (Newman Projection) of CF3CH3?

Is a totally eclipsed Newman projection the most stable conformation for a 2 carbon compound, with one carbone bonded to more electronegative atoms (making them partial negative), and the other carbon ...
1
vote
0answers
26 views

Why atropisomers are called conformers?

Changing one atropisomer to another requires bond breaking (in some cases the removal and reattachement of steric groups, according to my understanding) so how it is possible that according to IUPAC ...
-1
votes
1answer
48 views

what is superimposability of mirror images of this molecule? [closed]

I don't get why (a) and (d) are achiral when we cant superimpose their respective mirror images?Or can we superimpose them?
0
votes
2answers
217 views

Fischer projections

Can somebody tell me how why they changed/choose the groups for vertical and horizontal lines. As far as I know the vertical lines represent group going away from us and horizontal depicts coming ...
2
votes
2answers
327 views

Stability of geometrical isomers in cycloalkanes

Among the following, which should be the most stable compound? 1)Cis-cyclohexane-1,2-diol 2)Trans-cyclohexane-1,2-diol 3)Cis-cyclohexane-1,3-diol 4)Trans-cyclohexane-1,3-diol My thought process is-...
1
vote
0answers
75 views

Which of the following molecules are enantiomers? [closed]

My book says that only molecule 7 is enantiomer of molecule 1. Why is this? Why can't molecule 1 and 2 be enantiomers?
1
vote
1answer
124 views

Are Anomers Epimers?

epimers are the class of stereoisomers which differ along configuration at any carbon in a carbohydrate(generally), And anomers are the kind of stereo isomers that differ at the carbonylic carbon, ...
2
votes
1answer
179 views

Stereochemistry of 1,4 disubstituted cyclohexane [closed]

How are these cyclohexanes identical?
2
votes
2answers
128 views

Can chiral atoms have same substituents but with different orientations?

So consider this molecule. We have to determine whether nitrogen atom is chiral or not. MY IDEAS: Now going by all I have read, for chiral atoms only criteria is substituents to be different. Here ...
10
votes
5answers
1k views

If a chiral molecule reacts with an achiral molecule will the product be chiral or achiral?

My book says that a pair of enantiomers will react the same way with an achiral substance. How is this possible? Does this imply that the product is achiral, even though the enantiomers are chiral? ...
7
votes
2answers
144 views

Number of spatial arrangements of tetrasubstituted biphenyl

According to my book 2-bromo-2'-(1-chloroethyl)-6'-iodo-6-(prop-1-en-1-yl)-1,1'-biphenyl has eight possible spatial arrangements. How can this be so? I can think of only four – left two groups being ...
2
votes
1answer
221 views

Cahn–Ingold–Prelog priority of CN vs CH2NH2

Why does $\ce{CH2NH2}$ have lower priority than $\ce{CN}$? The carbon on the first molecule is bonded to (N,H,H) while the carbon on the second molecule is just bonded to (N). I can't seem to find ...
0
votes
0answers
44 views

What compounds give two products on reacting with NH2OH?

This is a question from the chapter stereochemistry of my coaching module. The answer options include CH3CHO, DCHO, etc. How do I do this? I have an idea that if we take a racemic mixture of D and L ...
6
votes
2answers
471 views

Do you assume undrawn hydrogens are pointing away from you when determining R/S?

When determining R/S of stereoisomers, the group with the smallest atomic number needs to be in the back (dashed line). But if no group attached to a chiral center is drawn in dashed line, do we ...
-1
votes
1answer
87 views

Twisting stereoisomers with rings to determine R/S [closed]

I know that if the smallest atomic number group is not in the back, we can twist the molecule so that it is in the back and then determine if it is R/S (Left image). But if the chiral center is ...
-1
votes
1answer
82 views

Stereogenic Center Question

In cholesterol, I don't understand why the two points I circled are stereogenic centers. Isn't the left carbon attached to an OH, H, CH2, and CH2? And isn't the right carbon attached to CH, CH2, CH, ...
-1
votes
1answer
536 views

Explain optical activity in Biphenyl compounds

How is optical activity explained in biphenyl compounds using atropisomerism. NOTE: I was taught that if vertical symmetry exists then optical activity is not shown by any substituted biphenyl ...