53

Intriguing question. First, the best yield would be achieved by selectively producing one enantiomer instead of the other. In this case, White wants D-methamphetamine (powerful psychoactive drug), not L-methamphetamine (Vicks Vapor Inhaler). Reaction processes designed to do this are known as "asymmetric synthesis" reactions, because they favor production ...


50

That's a good, concise statement of Bent's rule. Of course we could have just as correctly said that p character tends to concentrate in orbitals directed at electronegative elements. We'll use this latter phrasing when we examine methyl fluoride below. But first, let's expand on the definition a bit so that it is clear to all. Bent's rule speaks to the ...


28

$\alpha$-D-glucose and $\beta$-D-glucose are stereoisomers - they differ in the 3-dimensional configuration of atoms/groups at one or more positions. $\alpha$-D-glucose $\beta$-D-glucose Note that the structures are almost identical, except that in the $\alpha$ form, the $\ce{OH}$ group on the far right is down, and, in the $\beta$ form, the $\ce{OH}...


27

Asked and answered, but I think one thing that's missing is that allenes are not planar like alkenes or alkynes are. You can refer to this question for an explanation. The dihedral angle between the two halogens is 90 degrees (ideally). Here's an animation hopefully providing a better view of the 3D structure: This results in the two mirror images being ...


26

The D-L system corresponds to the configuration of the molecule: spatial arrangement of its atoms around the chirality center. While (+) and (-) notation corresponds to the optical activity of the substance, whether it rotates the plane of polarized light clockwise (+) or counterclockwise (-). D-L system tells us about the relative configuration of the ...


26

It's not easy to see from a diagram, because it distorts bonds and angles. I recommend building it with a balls-and-sticks model set. You can also use a molecular viewer to model it; there are a couple of open-source (or at least free) ones out there. I have calculated the molecule on the DF-BP86/def2-SVP level of theory. The point group of the molecule is ...


25

since for every orientation of the molecule, we can reverse the orientation such that the light appears to be falling on the molecule from a direction other than the one for our original molecule. This is false. Let's take 2-butanol. For this stereoisomer, light is turning clockwise when viewed from the right side (I'm not sure of this, but we can assume). ...


25

Generally, amine nitrogens will not behave like a normal asymmetric carbon. Simple amines are roughly $\mathrm{sp^3}$ hybridiized and the molecules you use as examples do have 4 (we include the lone pair of electrons as a substituent) different substituents around the central nitrogen atom. So in principle me might consider it asymmetric or chiral. But ...


25

cis-1,2-Dimethylcyclohexane is achiral, not because there is a plane of symmetry, but because it consists of two enantiomeric conformations which interconvert rapidly via ring flipping at normal temperatures. This is exactly the same case as amine inversion. "Chiral nitrogens" such as that in $\ce{NHMeEt}$ do not lead to chirality or optical activity ...


25

Racemization isn't "exact," but rather very very close to equality. It is just simple probability. Think of flipping a coin, p=probability for heads, and q=probability of tails. Now for a fair flip p=q=0.5. From binomial theory the standard deviation is $\sqrt{n\cdot p \cdot q}$ where n is the number of flips. Now let's assume 2 standard deviations ...


23

Very interesting question! The key word you are looking for is planar chirality. In trans-cyclooctene, the polymethylene bridge can either go "in front of" or go "behind" the plane of the double bond, assuming you fix the double bond and the two hydrogens in place. As pointed out by @jerepierre, they are considered different molecules due to a high-energy ...


23

In compound A, the negative and double bonded oxygens bound to the phosphorus are equivalent: $\hspace{5.1cm}$ In compound B, they are not equivalent: $\hspace{7.5cm}$


22

Meth doesn't have to be optically pure to be "pure". A mixture of d,l-methamphetamine is still pure, but I get where you're going with this. He has a few options: Chiral resolution - he could make the racemic meth and they resolve it by selectively crystallizing out the desired enantiomer. Chiral acids like tartaric acid can be used to do this. He could ...


22

The strict criterion for a compound to display chirality is that it must not be superimposable upon its mirror image. Let's ignore the chair conformation of the ring for a while, and assume it adopts a planar conformation. You could draw a side-on view of the ring like this: Its mirror image would look like this. This is an example of axial chirality (...


21

Achiral cyclic compounds like 1,2,3-trichlorocyclopropane may contain pseudoasymmetric centers. Pseudoasymmetric centers have distinguishable ligands (“a”, “b”, “c”, “d”), two of which are nonsuperposable mirror images of each other (enantiomorphic). The lower case stereodescriptors “r” and “s” are used to designate the absolute configuration of ...


20

Chirality is a property of objects in which they lack certain symmetry operations, specifically improper rotations, including the mirror plane and inversion operations. For example, 3-dimensional chiral objects lack mirror symmetry. According to Wikipedia: The feature that is most often the cause of chirality in molecules is the presence of an asymmetric ...


20

Here is a 3-D conformer from PubChem As you can clearly see, a plane of symmetry can be sent along the black line perpendicular to the plane of the screen. Hence, the molecule is achiral. If you take a mirror image, you can ultimately super-impose it again on the parent form Here is an illustrative 3D image(courtesy of andselisk) which clearly shows the ...


19

The name (1​s,4​s)-1-ethyl-4-methylcyclohexane is correct; it is even the preferred IUPAC name (PIN). It refers to the cis isomer of 1-ethyl-4-methylcyclohexane. The preferred IUPAC name for the corresponding trans isomer is (1​r,4​r)-1-ethyl-4-methylcyclohexane. In general nomenclature, according to Subsection P-93.5.1.2 of the current version of ...


18

There is a reason for everything. Does Bent's rule have any utility? YES! It wouldn't be there if there was not. But I will get back to this at the end of this post. Let me go through the points raised by your teacher first: Coulombic considerations can be used to rationalize bond angles, strengths, and lengths without the use of Bent's rule. ...


18

I basically agree with Ron's answer, but had to draw all of the possible structures to confirm it. The complication is that carbon-2 is non-stereogenic but it may be chirotopic depending on the configuration of the neighboring atoms. The IUPAC Gold Book calls this a pseudo-asymmetric carbon atom. Carbon-2 is not a stereocenter, because it does not have four ...


18

Yes, this compound is chiral. The polycyclic backbone is called adamantane. It has $T_\mathrm{d}$ symmetry, meaning that as far as chirality goes, it behaves like a perfect tetrahedron, somewhat like methane does. It also has the interesting property that if you extend the C-F, C-Cl, ... bonds inwards, they will all meet at the same point. Those red dotted ...


18

The hindered rotation is due to the hydrogens at the naphthyl moiety. The following shows the rotation calculated at the DF-B97D3/def2-SVP level of theory. To better visualise this, I have chosen a mode with large atoms (not actually using the van-der-Waals radii, because that looked very strange; click here for a ball and stick version): We can observe ...


17

Yes . You are right that structural symmetry comes into play . Boiling point depends upon intermolecular interactions which over here is more in cis due to its net dipole moment . The dipole moment enables electronic interactions which hold molecules together . This shows some general factors of boiling point . Also the below link to the google book ...


17

Holding your hands in this way merely proves that your hands are mirror images. If you take any object (chiral or not) and hold it up to a mirror, you can always align common features. Imagine instead placing one of your hands inside the other. You may be able to align the overall thumbs and fingers, but they will be facing opposite directions, thus are not ...


16

But if i rotate my left hand by 180 degrees ie now palm of my left hand faces away from me then both the left and right hand are superimposable . Turning your hands this way only makes them superimposable if you make the assumption that they are two-dimensional objects, where the normal vectors coming out of both sides of a given hand are indistinguishable. ...


16

Good question. There's a phenomenon named cryptochirality[1] (meaning “hidden chirality”), when a compound, though chiral, has practically unmeasurable optical rotation activity. It can happen to molecules with chiral center(s) bearing very similar substituents. (So, no tricks with bonded slightly modified enantiomeric pairs are needed.) An example is 5-...


15

It is all about minimizing the energy of a molecule. In the case of carbon, the only molecule that adopts a perfect hexagonal geometry in its ground state is benzene (and its derivatives that possess a 6-fold rotational axis). In this case the hexagonal geometry is adopted because all of the carbons are $\ce{sp^2}$ hybridized. The ideal geometry (lowest ...


15

For a molecule to be chiral it must have non-superimposable mirror images. Here is a drawing of the two mirror images for 2-bromobutane. The chiral carbon atom is denoted by an asterisk. In the case of 2-bromobutane there are 4 different substituents attached to it. The molecule is chiral, you can't pick up one of the mirror images and superimpose it on ...


15

Background One can draw conformations of n-butane with the carbon-carbon bonds oriented in certain directions and the methyl hydrogens pointing in certain directions that are chiral. However, since rotation about single bonds is typically fast at room temperature, these chiral conformers of n-butane would only be resolvable at extremely low temperatures. ...


14

You have drawn the compounds correctly, and yes a solid wedge means the bond is coming out of the plane of the screen towards you a dashed wedge means the bond is going behind the plane of the screen away from you a solid line means the bond lies in the plane of the screen Here is a Newman projection of your molecules, sometimes Newman projections can ...


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