Organic Chemistry Chirality Quiz
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Questions and Answers

Which of the following molecules is described as achiral?

  • 2-bromopropanoic acid
  • Propan-2-ol (correct)
  • Butan-2-ol
  • 2-chlorobutane
  • Butan-2-ol contains four different groups attached to its tetrahedral carbon.

    True (A)

    What are mirror images of non-superimposable molecules called?

    enantiomers

    The presence of a single asymmetric carbon atom determines if a molecule is ___ or achiral.

    <p>chiral</p> Signup and view all the answers

    Match the following organic molecules with their chiral or achiral classification:

    <p>Propan-2-ol = Achiral Butan-2-ol = Chiral 2-chlorobutane = Chiral 2-bromopropanoic acid = Chiral</p> Signup and view all the answers

    Which of the following methods can help determine molecular chirality?

    <p>Constructing models and mirror images (C)</p> Signup and view all the answers

    An achiral molecule can be superimposed on its mirror image.

    <p>True (A)</p> Signup and view all the answers

    What type of reaction mechanism is described for the reaction between CH3Cl and hydroxide ion?

    <p>Substitution nucleophilic bimolecular (SN2) (B)</p> Signup and view all the answers

    The SN2 reaction mechanism involves one step and does not form intermediates.

    <p>True (A)</p> Signup and view all the answers

    The rotation of butan-2-ol's mirror image by 180° results in a structure that is ___ on its original form.

    <p>non-superimposable</p> Signup and view all the answers

    Who proposed the mechanism for the SN2 reaction in 1937?

    <p>Edward Davies Hughes and Sir Christopher Ingold</p> Signup and view all the answers

    In an SN2 reaction, the incoming nucleophile interacts with the alkyl halide to break the __________ bond.

    <p>carbon-halide</p> Signup and view all the answers

    Match the following components of the SN2 reaction with their descriptions:

    <p>Incoming nucleophile = Hydroxide ion Leaving group = Chloride ion Transition state = Partially bonded nucleophiles Reaction type = Bimolecular</p> Signup and view all the answers

    Which statement describes the kinetics of the SN2 reaction between CH3Cl and hydroxide ion?

    <p>The reaction rate depends on the concentration of both reactants. (B)</p> Signup and view all the answers

    In the transition state of an SN2 reaction, all three carbon-hydrogen bonds are in the same plane.

    <p>True (A)</p> Signup and view all the answers

    What happens to the bonds as the attacking nucleophile approaches the carbon atom during an SN2 reaction?

    <p>The carbon-hydrogen bonds start moving away from the attacking nucleophile.</p> Signup and view all the answers

    What is the term used when a single product is formed from an asymmetric carbon that retains its configuration?

    <p>Retention (D)</p> Signup and view all the answers

    Inversion of configuration occurs when an asymmetric carbon is replaced with a group that maintains the original configuration.

    <p>False (B)</p> Signup and view all the answers

    What are the three possible outcomes for a reaction at an asymmetric carbon atom?

    <p>Inversion, retention, and racemisation</p> Signup and view all the answers

    A 50:50 mixture of two enantiomers results in __________, which is optically inactive.

    <p>racemisation</p> Signup and view all the answers

    Which statement correctly describes the outcome of an SN2 reaction involving optically active alkyl halides?

    <p>It results in inversion of configuration. (D)</p> Signup and view all the answers

    SN1 reactions of optically active alkyl halides result in inversion of configuration.

    <p>False (B)</p> Signup and view all the answers

    In SN2 reactions, the nucleophile attacks the carbon atom on the side __________ to the leaving group.

    <p>opposite</p> Signup and view all the answers

    Match the following type of reaction with its outcome:

    <p>SN1 = Racemisation SN2 = Inversion of configuration Retention = Same configuration Racemisation = Optically inactive product</p> Signup and view all the answers

    Which of the following metallic fluorides is NOT mentioned as suitable for the synthesis of alkyl fluorides?

    <p>NaF (D)</p> Signup and view all the answers

    The Swarts reaction involves the synthesis of alkyl chlorides from alkyl bromides.

    <p>False (B)</p> Signup and view all the answers

    What is formed when a primary aromatic amine is treated with sodium nitrite in acid?

    <p>Diazonium salt</p> Signup and view all the answers

    Electrophilic substitution of arenes with chlorine and bromine requires the presence of a __________ acid catalyst.

    <p>Lewis</p> Signup and view all the answers

    Match the following reagents with their corresponding reactions in haloalkane synthesis:

    <p>AgF = Synthesis of alkyl fluorides NaNO2 = Formation of diazonium salt HNO3 = Oxidation during iodination CuCl = Replacement of diazonium group by chloride</p> Signup and view all the answers

    In the preparation of haloarenes, which statement is true regarding dihalogen derivatives of propane?

    <p>Different isomers can exist for dihalogen derivatives. (B)</p> Signup and view all the answers

    Fluoro compounds can be prepared using electrophilic substitution reactions with fluorine.

    <p>False (B)</p> Signup and view all the answers

    Identify the reagent that is used to oxidize HI formed during iodination.

    <p>HNO3 or HIO4</p> Signup and view all the answers

    What determines the route taken by an alkyl halide when reacted with a base or nucleophile?

    <p>Nature of alkyl halide, strength and size of base/nucleophile, and reaction conditions (C)</p> Signup and view all the answers

    A tertiary alkyl halide prefers an SN2 reaction over elimination.

    <p>False (B)</p> Signup and view all the answers

    What type of compounds are formed when organic chlorides, bromides, and iodides react with metals?

    <p>Organo-metallic compounds</p> Signup and view all the answers

    Grignard reagents are formed by the reaction of haloalkanes with ________ in dry ether.

    <p>magnesium metal</p> Signup and view all the answers

    Which reaction mechanism is preferred by primary alkyl halides?

    <p>SN2 (A)</p> Signup and view all the answers

    Match the following types of alkyl halides with their preferred reaction types:

    <p>Primary alkyl halides = SN2 Secondary alkyl halides = SN2 or elimination Tertiary alkyl halides = SN1 or elimination Bulkier nucleophiles = Act as bases</p> Signup and view all the answers

    Victor Grignard was first trained in chemistry before moving to mathematics.

    <p>False (B)</p> Signup and view all the answers

    In what year did Victor Grignard first report his work related to Grignard reagents?

    <p>1900</p> Signup and view all the answers

    What reaction involves a mixture of an alkyl halide and aryl halide treated with sodium in dry ether to produce an alkylarene?

    <p>Wurtz-Fittig reaction (A)</p> Signup and view all the answers

    Chloroform is typically used as a solvent for fats and alkaloids.

    <p>True (A)</p> Signup and view all the answers

    What type of compounds are referred to as polyhalogen compounds?

    <p>Carbon compounds containing more than one halogen atom</p> Signup and view all the answers

    Dichloro- __________ is widely used as a solvent and paint remover.

    <p>methane</p> Signup and view all the answers

    Which of the following statements about methylene chloride is true?

    <p>It can cause dizziness and nausea at high exposure levels. (C)</p> Signup and view all the answers

    Match the following halogen compounds with their uses:

    <p>Dichloromethane = Solvent and paint remover Chloroform = Production of the refrigerant R-22 Trichloromethane = Solvent for fats and alkaloids Propellant = In aerosol products</p> Signup and view all the answers

    What is the major use of chloroform today?

    <p>Production of the freon refrigerant R-22</p> Signup and view all the answers

    Direct contact with methylene chloride can cause intense burning and redness of the skin.

    <p>True (A)</p> Signup and view all the answers

    Flashcards

    How are aryl chlorides and bromides prepared?

    Aromatic chlorides and bromides can be prepared by reacting an arene with chlorine or bromine in the presence of a Lewis acid catalyst, such as iron or iron(III) chloride.

    What is the Swarts reaction?

    A reaction where an alkyl chloride or bromide is converted into an alkyl fluoride by heating it with a metallic fluoride like AgF, Hg2F2, CoF2, or SbF3.

    What is Sandmeyer's reaction?

    The substitution of a diazonium group (-N2+) in a primary aromatic amine by a halogen. It involves reacting a diazonium salt with cuprous halides (CuCl or CuBr) to form aryl chlorides or bromides.

    How is the diazonium group replaced by iodine in Sandmeyer's reaction?

    Iodine does not require a cuprous halide in Sandmeyer's reaction. The reaction of the diazonium salt with potassium iodide directly replaces the diazonium group with iodine.

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    Why is sulphuric acid not used during the reaction of alcohols with KI?

    Sulphuric acid can oxidize iodide ions (I-) to iodine (I2), which can then react with the alcohol to form an alkyl iodide. This side reaction can lead to unwanted products.

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    What are dihalogen derivatives of propane?

    A molecule where two halogen atoms are attached to a propane molecule. There are various possibilities for the position of these halogens, leading to different isomers like 1,1-dichloropropane, 1,2-dichloropropane, 1,3-dichloropropane, etc.

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    Which isomer of C5H12 produces only one monochloride upon photochemical chlorination?

    The only isomer of C5H12 that yields a single monochloride upon photochemical chlorination is neopentane (2,2-dimethylpropane). This is because all the hydrogen atoms in neopentane are equivalent.

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    How does photochemical chlorination work?

    The reaction is photochemical, meaning it requires light to proceed. When light is absorbed, the chlorine molecule breaks into chlorine radicals. These radicals then abstract hydrogen atoms from the alkane, leading to the formation of alkyl radicals. The alkyl radicals then combine with chlorine radicals to form monochlorides.

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    SN2 reaction

    A reaction mechanism where a nucleophile attacks a molecule from the back side, causing the leaving group to depart simultaneously. This happens in a single step, with no intermediate formation.

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    Nucleophile

    A species that donates an electron pair to form a new bond with an electrophile.

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    Leaving Group

    A species that leaves a molecule during a reaction, taking with it the electron pair it was sharing.

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    Chiral molecule

    A molecule with a carbon atom bonded to four different groups, making it non-superimposable on its mirror image.

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    Achiral molecule

    A molecule that is superimposable on its mirror image, meaning it lacks an asymmetric carbon.

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    Asymmetric carbon

    The carbon atom in a chiral molecule that is bonded to four different groups, making it the center of chirality.

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    Enantiomers

    Two stereoisomers that are non-superimposable mirror images of each other, like your left and right hands.

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    Chirality

    The ability of a molecule to exist in two non-superimposable mirror image forms, due to the presence of an asymmetric carbon.

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    Molecular model

    A model used to represent the three-dimensional structure of a molecule, allowing us to visualize its chirality.

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    Superimposition

    The process of comparing the structures of a molecule and its mirror image to determine if they are superimposable.

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    Molecular chirality test

    A method for determining chirality by constructing and comparing molecular models or visualizing the three-dimensional structure of a molecule and its mirror image.

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    Configuration Retention

    A reaction where the configuration of a chiral center remains the same, but the sign of its optical rotation changes.

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    Configuration Inversion

    A reaction where the configuration of a chiral center is reversed, leading to a change in the sign of optical rotation.

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    Racemization

    A reaction where a mixture of enantiomers is formed, resulting in a racemic mixture with zero net optical rotation.

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    Optically Active Alkyl Halides

    A compound that contains one or more asymmetric carbon atoms, resulting in the existence of enantiomers.

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    Optical Activity

    A molecule that can rotate the plane of polarized light, either to the right (dextrorotatory) or to the left (laevorotatory).

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    Racemic Mixture

    A 50:50 mixture of a pair of enantiomers, resulting in no net optical rotation.

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    Substitution vs. Elimination

    A reaction involving an alkyl halide with beta-hydrogen atoms and a base/nucleophile, leading to either substitution or elimination of a leaving group.

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    Elimination Reaction

    A reaction where a base/nucleophile removes a proton from a beta-carbon, leading to the formation of a double bond. Favored by strong bases and bulky nucleophiles.

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    Organometallic Compounds

    Compounds containing a carbon-metal bond, often formed by the reaction of haloalkanes with metals.

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    Grignard Reagent

    A type of organometallic compound formed by reacting haloalkanes with magnesium metal in dry ether. They are highly reactive and useful for carbon-carbon bond formation.

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    Sandmeyer's Reaction

    A chemical reaction in which a diazonium salt reacts with a cuprous halide to form an aryl chloride or bromide. It's a key method for introducing halogens into aromatic compounds.

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    Swarts Reaction

    A reaction where an alkyl chloride or bromide undergoes a substitution reaction with a metallic fluoride to form an alkyl fluoride.

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    Wurtz-Fittig reaction

    A reaction where an alkyl halide and aryl halide are treated with sodium in dry ether, resulting in the formation of an alkylarene.

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    Fittig reaction

    A reaction where two aryl halides are treated with sodium in dry ether, resulting in the formation of a compound with two joined aryl groups.

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    Polyhalogen compound

    A compound containing more than one halogen atom bound to the same carbon chain.

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    Dichloromethane (Methylene chloride)

    A solvent used in various applications like paint removal, aerosols, metal cleaning, and manufacturing of drugs. It has adverse effects on human health, causing central nervous system damage, skin irritation, and eye damage.

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    Chloroform (Trichloromethane)

    A solvent used for fats, alkaloids, iodine, and other substances. It's mainly used in the production of the refrigerant R-22. It harms the human central nervous system and skin upon contact.

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    Haloalkane (Alkyl halide)

    A class of organic compounds containing a halogen atom bonded to a saturated carbon atom. They undergo various reactions, including SN1 and SN2 reactions.

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    Haloarene (Aryl halide)

    A class of organic compounds containing a halogen atom bonded to an aromatic ring. They undergo similar reactions to haloalkanes but are less reactive.

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    SN2 reaction rate

    The rate at which a molecule reacts in a SN2 reaction is affected by the structure of the molecule. For example, a primary alkyl halide will react faster than a tertiary alkyl halide.

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    Study Notes

    Haloalkanes and Haloarenes

    • Halogenated compounds persist in the environment due to their resistance to breakdown by soil bacteria.

    • The replacement of hydrogen atoms in an aliphatic or aromatic hydrocarbon with halogen atoms forms alkyl halides (haloalkanes) and aryl halides (haloarenes).

    • Haloalkanes contain a halogen atom attached to an sp³ hybridized carbon atom of an alkyl group.

    • Haloarenes contain a halogen atom attached to an sp² hybridized carbon atom of an aryl group.

    • Many halogen-containing organic compounds are found in nature and some are clinically useful.

    • These compounds are used as solvents for nonpolar compounds and as starting materials for various organic compound syntheses.

    • Examples include antibiotics (chloramphenicol), hormones (thyroxine), or drugs (chloroquine).

    • Haloalkanes and haloarenes are also used as anesthetics (e.g., halothane) and potential blood substitutes.

    Nomenclature

    • Haloalkanes and haloarenes are named according to the IUPAC system.
    • For dihalogen substituted derivatives of benzene, common names use prefixes (o-, m-, p-) while IUPAC names use numbers (1,2; 1,3; 1,4).
    • IUPAC nomenclature for alkyl groups uses corresponding halide names.

    Classification

    • Compounds containing sp³ C-X bonds are further classified as alkyl halides, allylic halides and benzylic halides.
    • Alkyl halides are named by naming the alkyl group followed by the halide.
    • Alkyl halides are classified as primary, secondary, or tertiary depending on the type of carbon atom the halogen is attached to.

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    Description

    Test your knowledge on molecular chirality and its implications in organic chemistry. This quiz covers concepts related to achiral and chiral molecules, reaction mechanisms, and specific examples such as butan-2-ol. Determine your understanding of these fundamental concepts!

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