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Questions and Answers
Which of the following accurately describes the stability of carbocations in SN1 reactions?
What is the main factor impacting the mechanism of an SN2 reaction?
Which equation correctly represents the rate law for an SN1 reaction?
When identifying the major product of an elimination reaction, which factor primarily influences the outcome?
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Which type of alcohol will be oxidized to a ketone?
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What is the impact of solvent choice on SN1 and SN2 reactions?
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What characteristic distinguishes meso compounds in stereochemistry?
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Which statement correctly reflects the naming convention for alkenes using E/Z nomenclature?
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Study Notes
Optical Rotation and Stereoisomers
- Diastereomers: Stereoisomers that are not enantiomers (non-mirror images)
- Meso Compounds: Achiral molecules with chiral centers due to an internal plane of symmetry
- R/S Configuration: Assigning priority to substituents around a chiral center based on atomic number
SN1 and SN2 Reactions
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SN1: Two-step reaction, unimolecular rate-determining step, proceeds through a carbocation intermediate.
- Tertiary alkyl halides are most reactive due to stable tertiary carbocation
- Favored by polar protic solvents
- Rate law: Rate = k[alkyl halide]
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SN2: One-step reaction, bimolecular rate-determining step, proceeds through a concerted mechanism
- Primary alkyl halides are most reactive due to less steric hindrance
- Favored by polar aprotic solvents
- Rate law: Rate = k[alkyl halide][nucleophile]
Alkenes
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E/Z Naming: Assigning stereoisomers based on the priority of substituents on each carbon of the double bond
- E: Trans configuration with high-priority groups on opposite sides
- Z: Cis configuration with high-priority groups on the same side
Elimination Reactions
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Major Product Prediction: Identify the most substituted alkene as the major product
- The elimination reaction usually follows Zaitsev's rule
Addition Reactions
- Major Product Prediction: Identify the product based on the addition of the reagent across the double bond
Alcohols and Esters
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Oxidation of Alcohols:
- Primary alcohols (R-CH2OH) oxidize to aldehydes (R-CHO) and then carboxylic acids (R-COOH).
- Secondary alcohols (R2CHOH) oxidize to ketones (R2CO)
- Tertiary alcohols (R3COH) do not undergo oxidation.
- Esterification: The reaction between a carboxylic acid and an alcohol to form an ester and water.
- Hydrolysis: The reverse reaction of esterification, breaking an ester into a carboxylic acid and alcohol.
Cyclohexanes
- Naming: Use standard IUPAC naming conventions for cyclic compounds.
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Cis/Trans: Identifying the position of substituents relative to the plane of the ring
- Cis: Substituents on the same side of the ring
- Trans: Substituents on opposite sides of the ring
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Chair Conformations: The most stable conformation of a cyclohexane ring, with axial and equatorial positions.
- Axial: Substituents pointed up or down from the ring
- Equatorial: Substituents pointing out from the ring
- Ring Inversion: The interconversion between two chair conformations.
Carbohydrates
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D/L Configuration: Assigning chirality based on the position of the hydroxyl group on the penultimate carbon.
- D: Hydroxyl group on the right side
- L: Hydroxyl group on the left side
- Aldose/Ketose: Classifying sugars based on the presence of an aldehyde or a ketone.
- Haworth Projections: A cyclic representation of a carbohydrate ring.
- α/β Anomers: Different stereoisomers formed by ring closure, depending on the position of the anomeric hydroxyl group.
- Glucoside Links: The type of linkage between monosaccharide units in a polysaccharide.
- Hemi-acetal/Acetal: Anomers of a sugar exist as a hemiacetal, which can react with an alcohol to form an acetal for stability.
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