Organic Chemistry Reactions Quiz

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Questions and Answers

What is the primary purpose of adding red phosphorus (P) in the given reaction?

  • To increase the concentration of I2
  • To catalyze the formation of HI
  • To remove I2 formed during the reaction (correct)
  • To enhance the reaction rate

Which reagent is used in Clemmensen reduction?

  • Zinc amalgam and concentrated HCl (correct)
  • Potassium permanganate
  • Lithium aluminum hydride
  • Sodium borohydride

What type of compounds does the Wolf-Kishner reaction reduce?

  • Alkanals and alkanones (correct)
  • Alcohols and phenols
  • Esters and ethers
  • Only alkanes

What does Zerewitnoff's method determine?

<p>The number of active hydrogen atoms in a compound (D)</p> Signup and view all the answers

Which reaction mechanism involves Grignard reagents reacting with alkyl halides to produce higher alkanes?

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

What distinguishes the Corey-House synthesis from other reactions?

<p>It is suitable for the preparation of unsymmetrical alkanes (D)</p> Signup and view all the answers

What is one of the products formed when Grignard reagent reacts with a carbonyl group?

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

Which of the following statements about the Corey-House reaction is accurate?

<p>It can yield both symmetrical and unsymmetrical alkanes (A)</p> Signup and view all the answers

Which hydrolysis results in the formation of methane?

<p>Both Al4C3 and Be2C (B)</p> Signup and view all the answers

What is the order of boiling points for the n-alkanes based on molecular weight?

<p>Hexane &lt; Pentane &lt; Heptane (B)</p> Signup and view all the answers

Which of the following compounds does not produce alkane when reacted with R—Mg—X?

<p>Acetic acid (CH3COOH) (B)</p> Signup and view all the answers

In Clemmensen's reduction, which reagent is used?

<p>Zn-Hg/HCl (D)</p> Signup and view all the answers

Which factor most significantly influences the boiling point of n-alkanes?

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

What trend do alkane melting points show among even and odd numbered carbon chains?

<p>Even numbered chains have higher melting points (B)</p> Signup and view all the answers

Why do alkanes with odd-numbered carbon atoms exhibit an abnormal trend in melting points?

<p>They pack poorly in crystal lattice (D)</p> Signup and view all the answers

What kind of solvent are alkanes soluble in?

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

What type of addition occurs during the hydroboration of alkenes?

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

Which reagent is used in the process of oxymercuration to treat alkenes?

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

What rule does the oxymercuration reaction adhere to?

<p>Markovnikov's rule (A)</p> Signup and view all the answers

What is the product of oxymercuration followed by reduction with sodium boro hydride?

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

What intermediate is formed during the oxymercuration process?

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

Which of the following is a step in the mechanism of oxymercuration?

<p>Formation of an alkyl mercuric cation (D)</p> Signup and view all the answers

During the hydroboration of alkenes, which carbon receives the nucleophile from BH3?

<p>Carbon with fewer hydrogen atoms (A)</p> Signup and view all the answers

Which reagent is combined with the oxymercuration product to complete the reaction to an alcohol?

<p>Sodium boro hydride (D)</p> Signup and view all the answers

What happens to the C—C bonds of alkanes when subjected to high temperature and pressure during the reaction?

<p>They break and form a mixture of nitroalkanes. (B)</p> Signup and view all the answers

Which compound is produced in the reaction between CH3—CH3 and HNO3 under high temperature?

<p>A mixture including nitroalkanes. (C)</p> Signup and view all the answers

What is the main result of sulphonation of alkanes?

<p>Replacement of hydrogen with sulfuric acid. (B)</p> Signup and view all the answers

Which alkane structure is the most reactive towards sulphonation?

<p>Tertiary hydrogen structure. (D)</p> Signup and view all the answers

In the provided reaction, what is the major product formed when CH2Br is exposed to light?

<p>CH3—CH3. (B)</p> Signup and view all the answers

Which of the following statements about nitroalkanes is accurate?

<p>They are formed through nitration reactions. (D)</p> Signup and view all the answers

What characterizes the sulphonation reaction in terms of the reagents used?

<p>It uses fuming H2SO4 or oleum. (B)</p> Signup and view all the answers

Which of the following nitroalkanes is considered the major product of the reaction involving propanes?

<p>2-Nitro propane. (C)</p> Signup and view all the answers

What is the primary characteristic of unimolecular elimination (E1)?

<p>It occurs via a carbocation intermediate. (B)</p> Signup and view all the answers

What happens during the first step of the unimolecular elimination reaction?

<p>The alcohol accepts a proton (H+) from the acid. (A)</p> Signup and view all the answers

Why is the cleavage of the C-O bond in the E1 mechanism considered the rate-determining step?

<p>It is the slowest step in the mechanism. (D)</p> Signup and view all the answers

What effect does the presence of a positive charge on the electronegative oxygen have during the E1 reaction?

<p>It weakens the C-O bond, making it easier to break. (C)</p> Signup and view all the answers

In the provided reaction mechanism, what is the role of the acid (H2SO4) in the E1 reaction?

<p>It protonates the alcohol, enabling the formation of a carbocation. (B)</p> Signup and view all the answers

Which step in the E1 mechanism is typically considered slow and rate-limiting?

<p>The formation of the ethyl carbocation. (A)</p> Signup and view all the answers

What type of elimination is characterized by the removal of H and X from adjacent C-atoms?

<p>Bimolecular elimination (E2) (A)</p> Signup and view all the answers

What product is primarily formed from the reaction of CH3-CH2-OH in the E1 mechanism?

<p>Ethylene (CH2=CH2) (B)</p> Signup and view all the answers

What is the primary mechanism responsible for adding bromine to alkenes in this context?

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

Which reaction product is formed when CH3–CH=CH2 is treated with HCl and ROOR?

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

In the chain initiation step, which components are primarily generated?

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

What stabilizes the 2° free radical formed during the chain propagation step?

<p>Hyperconjugation (C)</p> Signup and view all the answers

What is the result of the chain termination step involving CH3–CH–CH2–Br and Br?

<p>Formation of dibromide (C)</p> Signup and view all the answers

Which statement best describes the effect of dil.H2SO4 in the presence of Hg+2 during hydration of an alkyne?

<p>It facilitates the formation of a carbocation (C)</p> Signup and view all the answers

Which type of radical is preferred for stable products in chain propagation reactions?

<p>Tertiary radicals (C)</p> Signup and view all the answers

What does the term 'Anti Markownikoff's addition' imply in the context of the halogenation reaction?

<p>Addition at the least substituted carbon (B)</p> Signup and view all the answers

Flashcards

Clemmensen Reduction

A reduction reaction using zinc amalgam (Zn-Hg) and concentrated hydrochloric acid (HCl) to convert a carbonyl compound (ketone) to an alkane.

Red Phosphorus in Alkane Halogenation

Red phosphorus (P) is used to remove iodine (I2) formed in the reaction between an alkane and iodine.

Wolf-Kishner Reduction

A reaction involving the treatment of a carbonyl compound with hydrazine (NH2NH2) followed by a strong base (OH-) and heat to form an alkane.

Zerewitnoff's Method

A method to determine the number of active hydrogen atoms (H-atoms) in a compound. Grignard reagent (R-Mg-X) reacts with the compound and forms an alkane, releasing an equivalent of methane gas.

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Grignard Reagent with Alkyl Halide

A reaction between a Grignard reagent (R-Mg-X) and an alkyl halide (R'-X) to form a higher alkane.

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Corey-House Synthesis

A synthetic method for the preparation of unsymmetrical alkanes (R-R'). It involves the reaction of an alkyl halide with lithium followed by copper halide and another alkyl halide.

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Corey-House Reaction

A reaction which combines two alkyl halides (R-X and R'-X) to form an alkane, using lithium and copper halide as catalysts.

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Grignard Reagent and Active Hydrogen

A reaction where a Grignard reagent (R-Mg-X) reacts with a compound having active hydrogen to form an alkane.

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Alkane Solubility

Alkanes are hydrocarbons that contain only single bonds between carbon atoms. They are non-polar molecules, making them insoluble in water but soluble in non-polar solvents like benzene, carbon tetrachloride, and ether.

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Alkane Boiling Point

The boiling point of alkanes increases with increasing molecular weight. This is because the intermolecular forces (Van der Waals forces) become stronger as the molecules get larger.

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Branching Effect on Alkane Boiling Point

The boiling point of branched alkanes is lower than their straight-chain isomers. This is because branching reduces the surface area of the molecule, weakening the Van der Waals forces.

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Alkanes with Even Carbon Atoms

The melting point of alkanes with an even number of carbon atoms is generally higher than their odd-numbered counterparts. This is due to their ability to pack more tightly in a crystal lattice.

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Hydrolysis of Metal Carbides

Alkanes can be obtained from the hydrolysis of beryllium and aluminum carbides. This reaction involves the reaction of the carbide with water to produce an alkane and a metal hydroxide.

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Methyl Grignard Reagent Reactions

Methyl Grignard reagents (R-Mg-X) react with various compounds to form alkanes. However, they do not react with phenols (Ph-OH), benzene (C6H6), or carboxylic acids (CH3COOH).

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What is nitration?

The process of replacing a hydrogen atom in an alkane with a nitro group (-NO2).

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What are the conditions necessary for alkane nitration?

Nitration of alkanes is carried out at high temperatures (400-500°C) and under pressure. These conditions favor the breaking of C-H bonds, leading to the formation of nitroalkanes.

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Why do we get a mixture of nitroalkanes in nitration?

Due to the harsh conditions, the C-C bonds in alkanes can also break during nitration, resulting in a mixture of nitroalkanes.

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What is sulphonation?

The replacement of a hydrogen atom in an alkane with a sulfonic acid group (-SO3H).

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What reagents are used for alkane sulphonation?

Sulphonation of alkanes is typically performed with fuming sulfuric acid (H2SO4) or oleum (H2S2O7).

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What is the reactivity order for sulphonation?

The reactivity of different hydrogen atoms in an alkane towards sulphonation follows this order: tertiary (3°) > secondary (2°) > primary (1°).

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What type of alkanes are most prone to sulphonation?

Sulphonation is most commonly observed in higher alkanes and those with tertiary hydrogen atoms.

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E2 Elimination

A type of elimination reaction where the removal of a proton (H+) and a leaving group (X) from adjacent carbon atoms occurs in a single step, with a concerted mechanism involving both the base and the substrate.

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E1 Elimination

A type of elimination reaction where the removal of a proton (H+) and a leaving group (X) from adjacent carbon atoms occurs in two steps, with the formation of a carbocation intermediate.

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Rate-determining step in E1

The rate of an E1 reaction is determined by the rate of formation of the carbocation intermediate.

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Acidic Dehydration of Alcohol

A reaction that involves the removal of water from an alcohol molecule, usually using an acid catalyst.

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Protonation of Alcohol

The process of adding a proton (H+) to an alcohol molecule, which increases its positive charge and weakens the C-O bond.

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Carbocation

A species with a positive charge located on a carbon atom, formed during the E1 reaction.

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Deprotonation of Carbocation

A reaction where the intermediate carbocation loses a proton (H+) from a carbon atom adjacent to the positively charged carbon, leading to the formation of an alkene.

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Formation of Water

The step where a proton (H+) and a hydroxide ion (OH-) combine to form water.

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Halogenation of Alkanes

A reaction where a hydrogen atom is replaced by a halogen atom in an alkane. The reaction proceeds via a free radical mechanism, typically initiated by sunlight or peroxides.

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Hydrogenation

A hydrogen atom is added to an alkene or alkyne via an electrophilic addition reaction. This addition occurs mainly by the Markovnikov rule, where the hydrogen atom is added to the carbon with the most hydrogen atoms already attached.

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Halogenation of Alkenes and Alkynes

A process that adds a halogen atom to an alkene or alkyne by forming a carbocation intermediate. The halogen atom adds preferentially to the carbon with more alkyl substituents.

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Hydration of Alkenes and Alkynes

The addition of water to an alkene or alkyne using a catalyst such as mercury(II) sulfate and sulfuric acid. This reaction typically follows the Markovnikov rule to form an alcohol.

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Grignard Reaction

The reaction between a ketone or aldehyde with a Grignard reagent to form an alcohol. This reaction adds a carbon chain onto the carbonyl group of the ketone or aldehyde.

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Anti-Markovnikov Addition

A reaction where a halogen is added to an alkene or alkyne in the presence of peroxides. This reaction proceeds anti-Markovnikov, meaning the halogen atom is added to the carbon with fewer hydrogen atoms already attached.

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Hydroboration-Oxidation

The addition of hydrogen atoms (H) to a carbon-carbon double bond (C=C) in a specific manner, where one H atom comes from BH3 and the other from H2O/H, following the Markovnikov's rule.

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Oxymercuration-Demercuration

An addition reaction where a mercuric acetate (Hg(OAc)2) in water is treated with an alkene, followed by reduction with sodium borohydride (NaBH4) in aqueous NaOH to yield an alcohol. This process follows the Markovnikov's rule.

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Syn Addition

The addition of a reagent across a double bond in a way that the two parts of the reagent add to the same side of the double bond.

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Reduction Reaction

A chemical reaction where electrons are added to a molecule, leading to a decrease in the oxidation state of the reacting species. This can involve adding hydrogen atoms or removing oxygen atoms.

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Markovnikov's Rule

A rule that states that in the addition of a protic acid (HX) to an unsymmetrical alkene, the hydrogen atom (H) of HX adds to the carbon atom of the double bond that already has the greater number of hydrogen atoms.

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Oxymercuration Intermediate

A cyclic cation intermediate forms during the oxymercuration reaction, preventing any rearrangement of the carbon skeleton.

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Electrophile in Oxymercuration

The electrophilic species in the oxymercuration reaction is formed from the reaction between mercuric acetate and water.

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Demercuration

The process of replacing the mercury (Hg) atom in the oxymercuration intermediate with a hydrogen atom (H) to form the final product.

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Study Notes

Organic Chemistry - Hydrocarbons

  • Hydrocarbons are compounds composed of carbon and hydrogen atoms
  • Alkanes are saturated hydrocarbons containing only single bonds
  • Alkenes are unsaturated hydrocarbons with at least one carbon-carbon double bond
  • Alkynes are unsaturated hydrocarbons containing at least one carbon-carbon triple bond

Alkanes

  • General formula: CnH2n+2
  • Physical properties: Generally nonpolar, insoluble in water, soluble in nonpolar solvents, boiling point increases with increasing molecular weight. Branched alkanes have lower boiling points than their straight-chain isomers.
  • Chemical properties: Relatively unreactive, undergo substitution reactions (e.g., halogenation) with free radical mechanisms, can also undergo complete or incomplete oxidation.
  • Methods of preparation: Hydrogenation of alkenes and alkynes, reduction of alkyl halides, Wurtz reaction

Alkenes

  • General formula: CnH2n
  • Physical properties: Generally nonpolar, insoluble in water, soluble in nonpolar solvents, boiling point increases with increasing molecular weight. Branched alkenes have lower boiling points than their straight-chain isomers.
  • Chemical properties: More reactive than alkanes due to the presence of the double bond, undergo addition reactions (e.g., halogen addition, hydrogenation, hydration), isomerization.
  • Methods of preparation: Elimination reactions from alcohols, dehydrohalogenation of alkyl halides.

Alkynes

  • General formula: CnH2n-2
  • Physical properties: Generally nonpolar, insoluble in water, soluble in nonpolar solvents, boiling point increases with increasing molecular weight. Slightly higher boiling points than corresponding alkenes.
  • Chemical properties: Highly reactive, undergo addition reactions (e.g., hydrogenation, halogenation, hydration), ozonolysis (breaking of triple bond).
  • Methods of preparation: Dehydrohalogenation of vicinal dihalides., from tetrahaloalkanes, using Grignard reagents, from metal carbides

General Methods of Preparation

  • Hydrogenation: Addition of hydrogen to unsaturated compounds (alkenes and alkynes) to produce saturated compounds (alkanes). This can be a catalytic process with various catalysts.
  • Halogenation: Addition of halogens to unsaturated compounds (alkenes and alkynes).
  • Hydration: Addition of water to unsaturated compounds (alkenes and alkynes) to produce alcohols.
  • Ozonolysis: Oxidative cleavage of alkenes and alkynes producing carbonyl compounds.
  • Hydroboration-oxidation: Syn addition of borane followed by oxidation creating an alcohol product. (Anti-Markovnikov's addition)
  • Oxymercuration-demercuration: Markovnikov addition of water across the double bond using mercuric acetate followed by reduction.
  • Polymerization: Joining of many repetitive units of a molecule together, often used to produce plastics and fibers

Important Concepts

  • Markovnikov's rule: Addition of reagents to alkenes, the more positive part of the reagent adds preferentially to the carbon with more hydrogen atoms in an alkene.
  • Saytzeff's rule: Elimination reactions in alkenes, the most substituted alkene is the major product
  • Free radical mechanisms: Reactions initiated by free radicals (e.g., halogenation of alkanes)
  • Electrophilic additions: Reactions that proceed via electrophilic attack on the double or triple bond.

Additional Notes

  • Isomerism: Different structures possible for the same molecular formula
  • Functional group: Specific group of atoms responsible for certain properties of organic molecules
  • Naming: IUPAC naming conventions for different classes of hydrocarbons

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