Textbook Question
Which of the following structures represent the same compound? Which ones represent different compounds?
(c)
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4. Alkanes and Cycloalkanes
Cis vs Trans
5:46 minutesProblem 7d
Textbook Question
Draw the structure that corresponds to the name provided.
(d) (2R,4Z)-5-bromopent-4-ene-1,2-diol
Verified step by step guidance1
Step 1: Break down the name systematically. The name '(2R,4Z)-5-bromopent-4-ene-1,2-diol' provides information about the structure. The parent chain is 'pent', indicating a five-carbon chain. The suffix '-ene' indicates the presence of a double bond, and '-diol' indicates two hydroxyl (-OH) groups.
Step 2: Identify the substituents and their positions. The '5-bromo' indicates a bromine atom attached to the fifth carbon. The '1,2-diol' indicates hydroxyl groups attached to the first and second carbons. The '(2R)' specifies the absolute configuration at carbon 2, and '(4Z)' specifies the geometry of the double bond at carbon 4.
Step 3: Place the double bond and assign the Z configuration. The double bond is between carbons 4 and 5. The 'Z' configuration means the higher-priority groups on each carbon of the double bond are on the same side. Use the Cahn-Ingold-Prelog priority rules to determine the priorities.
Step 4: Assign the stereochemistry at carbon 2. The '(2R)' configuration means the substituents around carbon 2 are arranged in a clockwise manner when viewed from a specific perspective. Assign priorities to the groups attached to carbon 2 (hydroxyl, hydrogen, and the rest of the chain) and orient them accordingly.
Step 5: Draw the complete structure. Start with the five-carbon chain, add the double bond between carbons 4 and 5 with the Z configuration, place the bromine on carbon 5, and add hydroxyl groups to carbons 1 and 2. Ensure the stereochemistry at carbon 2 is R.
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Video duration:
5mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereochemistry
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical properties and reactions. In the given compound, the (2R,4Z) notation indicates specific configurations at the chiral center and the geometry of the double bond, which are crucial for accurately drawing the structure.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In this case, the presence of a bromine atom and hydroxyl groups (-OH) indicates that the compound is a brominated alcohol, which influences its reactivity and properties.
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Nomenclature
Nomenclature in organic chemistry refers to the systematic naming of chemical compounds based on their structure and functional groups. The name (2R,4Z)-5-bromopent-4-ene-1,2-diol provides information about the carbon chain length, the position of the double bond, and the presence of substituents, which are essential for constructing the correct molecular structure.
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