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Which of the following are optically active?
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Ch. 4 - Isomers: The Arrangement of Atoms in Space
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 4 - Isomers: The Arrangement of Atoms in SpaceProblema 73a,b
Bruice 8th EditionCh. 4 - Isomers: The Arrangement of Atoms in SpaceProblema 73a,bCapitolo 4, Problema 73a,b
Draw the structure for a compound with molecular formula C2H2I2F2
a. that is optically inactive because it does not have an asymmetric center.
b. that is optically inactive because it is a meso compound.
Guida verificata passo dopo passo1
Step 1: Understand the molecular formula C2H2I2F2. This indicates the compound contains 2 carbon atoms, 2 hydrogen atoms, 2 iodine atoms, and 2 fluorine atoms. The task is to draw two different structures based on optical inactivity criteria.
Step 2: For part (a), identify a structure that is optically inactive due to the absence of an asymmetric center. An asymmetric center is a carbon atom bonded to four different groups. To ensure optical inactivity, arrange the substituents (I, F, H) symmetrically around the two carbon atoms, such that neither carbon atom has four different groups attached.
Step 3: For part (b), identify a structure that is optically inactive because it is a meso compound. A meso compound has multiple stereocenters but possesses an internal plane of symmetry, making it optically inactive. Arrange the substituents (I, F, H) around the two carbon atoms such that the molecule has stereocenters but also an internal plane of symmetry.
Step 4: Draw the structure for part (a). Place the two carbon atoms in the center, and attach the substituents symmetrically (e.g., one iodine and one fluorine on each carbon atom, with hydrogens completing the bonds). Ensure no asymmetric centers are present.
Step 5: Draw the structure for part (b). Place the two carbon atoms in the center, and arrange the substituents (e.g., one iodine and one fluorine on each carbon atom) such that the molecule has stereocenters but also an internal plane of symmetry. Verify that the structure meets the criteria for a meso compound.
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Optical Activity
Optical activity refers to the ability of a compound to rotate plane-polarized light. This property is typically observed in chiral molecules, which possess an asymmetric center (a carbon atom bonded to four different groups). Compounds that are optically inactive either lack chirality or have a specific symmetry that cancels out their optical activity.
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08:17
Mutorotation and Optical Activity
Chirality and Asymmetric Centers
Chirality is a geometric property of some molecules that makes them non-superimposable on their mirror images, akin to left and right hands. An asymmetric center, usually a carbon atom, is bonded to four distinct substituents, leading to two enantiomers. A compound without an asymmetric center cannot exhibit optical activity, making it optically inactive.
Video consigliato:
05:41Understanding Other Chiral Atoms
Meso Compounds
Meso compounds are a specific type of stereoisomer that contain multiple chiral centers but are achiral due to an internal plane of symmetry. This symmetry results in the cancellation of optical activity, even though the compound has chiral centers. Meso compounds are important in understanding how molecular symmetry influences optical properties.
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04:10The 3 rules of meso compounds.
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