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The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?
- a)R, S, R, S, S, R
- b)R, S, S, R, R, S
- c)S, R, S, S, S, S
- d)R, R, S, S, R, R
Correct answer is option 'A'. Can you explain this answer?
Verified Answer
The compound hexachlorosulfolipid belongs to a class of compounds call...
- Let’s look at the first stereocenter on the very left. In determining the priority, use the Cahn-Ingold-Prelog rules, which essentially tells us to arrange in terms of atomic number. The first stereocenter has a Cl, C, C attached, and since Cl has the highest atomic number, it has the highest priority. Then we have a C attached to H’s or attached to a Cl, and for the same reason, C with the Cl takes priority:
- Draw a circle connecting them in this order 1 → 2 → 3 → 1. Remember that clockwise is R and counterclockwise is S. If the H is sticking into the plane of the page, however, the configuration must be switched. For So the first stereocenter is R
- Following a similar procedure for the second stereocenter to determine that it has a S configuration. Here since Cl is pointed back into the page and H is pointed forward out of the page, the configuration is switched from R to S:
- Following a similar procedure for the second stereocenter to determine that it has an S configuration:
- Following a similar procedure for the third stereocenter to determine that it has an R configuration:
- Following a similar procedure for the fourth stereocenter to determine that it has an S configuration:
- Following a similar procedure for the fifth stereocenter to determine that it has an S configuration:
- Following a similar procedure for the sixth stereocenter to determine that it has a R configuration. So the correct order is R, S, R, S, S, and R:
Most Upvoted Answer
The compound hexachlorosulfolipid belongs to a class of compounds call...
- Let’s look at the first stereocenter on the very left. In determining the priority, use the Cahn-Ingold-Prelog rules, which essentially tells us to arrange in terms of atomic number. The first stereocenter has a Cl, C, C attached, and since Cl has the highest atomic number, it has the highest priority. Then we have a C attached to H’s or attached to a Cl, and for the same reason, C with the Cl takes priority:
- Draw a circle connecting them in this order 1 → 2 → 3 → 1. Remember that clockwise is R and counterclockwise is S. If the H is sticking into the plane of the page, however, the configuration must be switched. For So the first stereocenter is R
- Following a similar procedure for the second stereocenter to determine that it has a S configuration. Here since Cl is pointed back into the page and H is pointed forward out of the page, the configuration is switched from R to S:
- Following a similar procedure for the second stereocenter to determine that it has an S configuration:
- Following a similar procedure for the third stereocenter to determine that it has an R configuration:
- Following a similar procedure for the fourth stereocenter to determine that it has an S configuration:
- Following a similar procedure for the fifth stereocenter to determine that it has an S configuration:
- Following a similar procedure for the sixth stereocenter to determine that it has a R configuration. So the correct order is R, S, R, S, S, and R:
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The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?a)R, S, R, S, S, Rb)R, S, S, R, R, Sc)S, R, S, S, S, Sd)R, R, S, S, R, RCorrect answer is option 'A'. Can you explain this answer? for MCAT 2026 is part of MCAT preparation. The Question and answers have been prepared according to the MCAT exam syllabus. Information about The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?a)R, S, R, S, S, Rb)R, S, S, R, R, Sc)S, R, S, S, S, Sd)R, R, S, S, R, RCorrect answer is option 'A'. Can you explain this answer? covers all topics & solutions for MCAT 2026 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?a)R, S, R, S, S, Rb)R, S, S, R, R, Sc)S, R, S, S, S, Sd)R, R, S, S, R, RCorrect answer is option 'A'. Can you explain this answer?.
The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?a)R, S, R, S, S, Rb)R, S, S, R, R, Sc)S, R, S, S, S, Sd)R, R, S, S, R, RCorrect answer is option 'A'. Can you explain this answer? for MCAT 2026 is part of MCAT preparation. The Question and answers have been prepared according to the MCAT exam syllabus. Information about The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?a)R, S, R, S, S, Rb)R, S, S, R, R, Sc)S, R, S, S, S, Sd)R, R, S, S, R, RCorrect answer is option 'A'. Can you explain this answer? covers all topics & solutions for MCAT 2026 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for The compound hexachlorosulfolipid belongs to a class of compounds called chlorosulfolipids, which are integral components of algal membranes and are known to inhibit protein kinases. Some have been isolated from mussels and are linked to diarrhetic shellfish poisoning. Based on the wedge and dash structure below, what are the R and S designations from left to right for the stereocenters of this toxin?a)R, S, R, S, S, Rb)R, S, S, R, R, Sc)S, R, S, S, S, Sd)R, R, S, S, R, RCorrect answer is option 'A'. Can you explain this answer?.
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