How is this correct? (Organic; Stereochemistry)

In summary, the conversation discusses assigning enantiomers using Newman projections. There is confusion about whether the (R)-enantiomer should have the Br and Cl switched, and the correct direction for the 4th priority group. It is concluded that both a) 1-bromo-1-chloroethane and b) 1-bromo-1-methoxypropane are likely (S)-enantiomers.
  • #1
Marconis
5
0
Draw Newman projections depicting the (R)-enantiomer of each of the following:
a) 1-bromo-1-chloroethane
b) 1-bromo-1-methoxypropane

Picture3.png


Now, I am SURE that I am mistaken, but isn't that an (S)-enantiomer for each? Assigning priorities:

For a) Br > Cl > CH3 > H...right? So, wouldn't the (R)-enantiomer have the Br and Cl switched? With Br on the top, you have priority 1 at the top, 2 at the bottom right, 3 in the middle, and 4 on the bottom left. Isn't that a clockwise direction, with 4th priority facing away from us? Or, is that H facing towards us...help!

Same goes for b, I switched the OCH3 and the Br...Something is really messing me up that is causing me to do this. Thank you in advance!
 
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  • #2
Marconis said:
with 4th priority facing away from us? Or, is that H facing towards us...help!
When you assign R and S, you let the 4th priority group face away from you. I've been picturing it so that the central atom, presumably carbon, is in the middle and the 4th priority atom, presumably hydrogen, is eclipsed by the central carbon and points directly away from you.

anyway, I'm pretty sure a is S and b is also S too. maybe the key is wrong or we're both making the same mistake?
 
  • #3
Yeah, I really have no idea. A lot of answers have been wrong in the past, but for this chapter, it really grinds my gears not to have faith in the answer key.
 

FAQ: How is this correct? (Organic; Stereochemistry)

1. What is organic chemistry?

Organic chemistry is a branch of chemistry that deals with the study of carbon-based compounds, also known as organic compounds. These compounds make up the basis of life and are found in all living organisms. Organic chemistry plays a crucial role in many industries, including pharmaceuticals, agriculture, and materials science.

2. What is the importance of stereochemistry in organic chemistry?

Stereochemistry is the study of the three-dimensional structures of molecules and how they affect their properties and reactivity. In organic chemistry, this is crucial as even minor changes in a molecule's stereochemistry can drastically alter its behavior and function. Understanding stereochemistry is essential for designing and synthesizing new drugs, pesticides, and other important organic compounds.

3. What are some common types of stereoisomers in organic chemistry?

The most common types of stereoisomers in organic chemistry are enantiomers and diastereomers. Enantiomers are mirror images of each other and have the same physical and chemical properties, except for their interaction with other chiral molecules. Diastereomers, on the other hand, have different physical and chemical properties due to their differing stereochemistry.

4. How do you determine the stereochemistry of a molecule?

The stereochemistry of a molecule can be determined through various techniques, including X-ray crystallography, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry. These techniques allow scientists to visualize the three-dimensional structure of a molecule and determine its stereochemistry based on the arrangement of its atoms and bonds.

5. What is the relationship between chirality and stereochemistry?

Chirality refers to the property of a molecule to exist in two mirror-image forms. Stereochemistry is the study of the three-dimensional arrangement of atoms in a molecule. Therefore, chirality is an important aspect of stereochemistry, as chiral molecules have different stereochemistry and can exhibit different properties and behaviors.

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