Chirality And Stereoisomers - Dr. Neufeldt

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1. Post-BACON Quiz2. Which of the following correctly describes the enantiomer of "meth", the drug frequently seen in the hit TV show "Breaking Bad"?

Explanation

The enantiomer of "meth" is used in an over-the-counter medicine to help alleviate nasal congestion.

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About This Quiz
Chirality And Stereoisomers - Dr. Neufeldt - Quiz

Welcome to BACON AT UCLA.

You have recently been learning about chirality and stereoisomers. In this tutorial, you'll see how these topics connect to artificial sweeteners, medicines,... see morethe origins of life, and more! The estimated time needed to complete this tutorial is: 20-30 minutes.

Note: The tutorial includes short pre-BACON and post-BACON quizzes. Only your grades on the post-BACON quiz will be recorded. There are also questions embedded throughout the tutorial, on which you will not be graded.
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2. Post-BACON Quiz3. In the 1950's the 'wonder drug' thalidomide was prescribed to pregnant women for the treatment of morning sickness, but was halted because ___________________________________

Explanation

In the 1950s, the drug thalidomide was prescribed to pregnant women for morning sickness. However, it was halted because the (S) enantiomer of the drug caused birth defects. This means that one specific form of the drug, the (S) enantiomer, was responsible for the harmful effects on developing fetuses. The discovery of this link led to the discontinuation of thalidomide as a treatment for pregnant women.

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3. Post-BACON Quiz4. What hypothesis has come about, at least in part, because of the discovery of chiral amino acids in the Murchison meteorite, which landed in Australia in 1969?

Explanation

The correct answer suggests that the discovery of chiral amino acids in the Murchison meteorite implies that the origins of homochirality (the preference for one enantiomer over the other) might be extraterrestrial. This means that the meteorite could have brought these chiral molecules to Earth, potentially playing a role in the development of life on our planet.

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4. Post-BACON Quiz1. Which of the following compounds smells like lemons and is the enantiomer of a compound that smells like oranges?

Explanation

The compound that smells like lemons and is the enantiomer of a compound that smells like oranges is called limonene. Limonene is a naturally occurring compound found in the peels of citrus fruits, particularly lemons and oranges. It has a strong citrus scent and is commonly used as a flavoring agent in food and beverages. The enantiomer of limonene, called perillyl alcohol, also has a citrus-like odor but smells more like oranges.

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5. Pre-BACON Quiz1. Which of the following compounds smells like lemons and is the enantiomer of a compound that smells like oranges?

Explanation

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6. BACON at UCLA – Chirality and Stereoisomers Page 4 of 16 Assign the absolute configuration in (–)-limonene:

Explanation

In the given question, we are asked to assign the absolute configuration in (–)-limonene. The answer provided is S. Absolute configuration refers to the spatial arrangement of atoms or groups in a chiral molecule. In (–)-limonene, there is a chiral carbon atom, and the priority of the substituents attached to it can be determined using the Cahn-Ingold-Prelog priority rules. By assigning priorities to the substituents and rotating the molecule to align the lowest priority group away from us, we find that the rotation is counterclockwise, indicating an S configuration. Therefore, the correct answer is S.

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7. Pre-BACON Quiz3. In the 1950's the 'wonder drug' thalidomide was prescribed to pregnant women for the treatment of morning sickness, but was halted because ___________________________________

Explanation

In the 1950s, thalidomide was prescribed to pregnant women as a treatment for morning sickness. However, it was halted because the (S) enantiomer of the drug caused birth defects. This means that one specific form of the drug, the (S) enantiomer, was responsible for the harmful effects on the developing fetus. The (R) enantiomer, on the other hand, did not cause birth defects. This discovery led to the withdrawal of thalidomide from the market and stricter regulations on the use of drugs during pregnancy.

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8. BACON at UCLA – Chirality and Stereoisomers Page 12 of 16 Synthesis of Pharmaceuticals              Chiral reagents and catalysts can be used nowadays to make molecules of interest with control of absolute stereochemistry, but enzymes can also be used for this purpose.  One important drug that can be synthesized on kilogram scale using an enzyme is (+)-naproxen, which is an anti-inflammatory drug used by millions of people around the world. In this reaction, the lipase enzyme only reacts with one of the enantiomers of the racemic methyl ester. This gives (+)-naproxen and the unreacted (­–) enantiomer of the substrate. Identify the stereochemistry of (+)-naproxen:

Explanation

The stereochemistry of (+)-naproxen is S. This is because the lipase enzyme only reacts with one of the enantiomers of the racemic methyl ester, resulting in the formation of (+)-naproxen. Since the lipase enzyme is selective for a specific enantiomer, it determines the stereochemistry of the product. Therefore, the stereochemistry of (+)-naproxen is determined to be S.

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9. Pre-BACON Quiz2. Which of the following correctly describes the enantiomer of "meth", the drug frequently seen in the hit TV show "Breaking Bad"?

Explanation

The enantiomer of "meth" is used in an over-the-counter medicine to help alleviate nasal congestion. An enantiomer is a molecule that is a mirror image of another molecule but cannot be superimposed on it. In the context of the question, the enantiomer of "meth" refers to a specific molecule that has similar properties and effects as "meth" but is used for a different purpose, namely to alleviate nasal congestion. This answer choice is the only one that accurately describes the enantiomer of "meth" and its usage.

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10. BACON at UCLA – Chirality and Stereoisomers Page 6 of 16 (–)-Aspartame can be made from L-aspartic acid and L-phenylalanine methyl ester. Identify the absolute configuration of the two chiral centers. 

Explanation

The absolute configuration of the two chiral centers in the compound (-)-Aspartame is Blue = S and Red = S.

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11. Pre-BACON Quiz4. What hypothesis has come about, at least in part, because of the discovery of chiral amino acids in the Murchison meteorite, which landed in Australia in 1969?

Explanation

The correct answer is "the origins of homochirality might be extraterrestrial." This hypothesis suggests that the presence of chiral amino acids in a meteorite implies that the origins of homochirality, the preference for one enantiomer over another, could be from extraterrestrial sources. This discovery raises the possibility that the building blocks of life on Earth may have originated from outer space.

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Post-BACON Quiz2. Which of the following correctly describes the...
Post-BACON Quiz3. In the 1950's the 'wonder drug' thalidomide was...
Post-BACON Quiz4. What hypothesis has come about, at least in part,...
Post-BACON Quiz1. Which of the following compounds smells like lemons...
Pre-BACON Quiz1. Which of the following compounds smells like lemons...
BACON at UCLA – Chirality and Stereoisomers Page 4 of...
Pre-BACON Quiz3. In the 1950's the 'wonder drug' thalidomide was...
BACON at UCLA – Chirality and Stereoisomers Page 12 of...
Pre-BACON Quiz2. Which of the following correctly describes the...
BACON at UCLA – Chirality and Stereoisomers Page 6 of...
Pre-BACON Quiz4. What hypothesis has come about, at least in part,...
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