Organic Chemistry Halogenation and Reactivity Quiz

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Questions and Answers

What is the product formed when methane (CH4) reacts with chlorine (Cl2) in the presence of sunlight?

  • Methylene chloride (CH2Cl2)
  • Chloroform (CHCl3)
  • Carbon tetrachloride (CCl4)
  • Methyl chloride (CH3Cl) (correct)

Which of the following statements is TRUE about the reactivity of halogens towards alkane halogenation?

  • The reactivity decreases down the group. (correct)
  • The reactivity increases down the group.
  • The reactivity is independent of the position of the halogen in the periodic table.
  • The reactivity remains constant down the group.

What is the main product formed when propane (CH3CH2CH3) undergoes nitration?

  • 2-nitropropane (CH3CH(NO2)CH3)
  • A mixture of 1-nitropropane and 2-nitropropane. (correct)
  • 1-nitropropane (CH3CH2CH2NO2)
  • Nitroethane (CH3CH2NO2)

Which of the following alkanes undergoes sulfonation when treated with fuming H2SO4?

<p>Hexane (C6H14) (C)</p> Signup and view all the answers

What are the products formed when ethane (C2H6) undergoes complete combustion in the presence of oxygen?

<p>Carbon dioxide (CO2) and water (H2O) (D)</p> Signup and view all the answers

Which of the following statements is TRUE about the reactivity of alkanes towards halogenation?

<p>Tertiary carbons are the most reactive. (B)</p> Signup and view all the answers

What is the main reason for the decreasing reactivity of halogens down a group in the periodic table?

<p>Decreasing electronegativity of the halogen atoms. (C)</p> Signup and view all the answers

Which of the following reactions is NOT a characteristic reaction of alkanes?

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

What is the main product formed from the dehydrohalogenation of vicinal dihalides in the presence of zinc dust and an alcoholic solution?

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

Which method produces alkenes at the anode through electrolysis of sodium or potassium salts of dicarboxylic acid?

<p>Kolbe's electrolysis (C)</p> Signup and view all the answers

What is the main difference in melting point between cis and trans isomers of alkenes?

<p>Trans isomers generally have a higher melting point due to their greater symmetry and ability to form more stable crystal lattices. (D)</p> Signup and view all the answers

Which reaction condition favors the formation of trans alkenes?

<p>Reaction with Li in liquid ammonia (D)</p> Signup and view all the answers

What is the main characteristic that makes alkenes reactive?

<p>The presence of a double bond (B)</p> Signup and view all the answers

What is the product formed when tributyl borane is oxidized with hydrogen peroxide and hydroxide ions?

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

What is the most reactive hydrogen halide in alkene addition reactions?

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

Which of the following reactions occurs with a trans addition?

<p>Oxidation by peracids (RCO3H) (E)</p> Signup and view all the answers

Which rule predicts the regioselectivity of the addition of hydrogen halides to unsymmetrical alkenes?

<p>Markovnikov's Rule (B)</p> Signup and view all the answers

Which condition leads to the anti-Markovnikov addition of HBr to unsymmetrical alkenes?

<p>Presence of light or peroxides (D)</p> Signup and view all the answers

Which of the following is a test used to detect double bonds in alkenes?

<p>Oxidation by cold alkaline KMnO4 (C)</p> Signup and view all the answers

Which of the following reactions gives an alcohol as a product?

<p>Addition of water (B), Hydroboration followed by oxidation (D)</p> Signup and view all the answers

What is the product formed when a trans alkene is oxidized by a peracid?

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

What is the main difference between the addition of water and the hydroboration reaction?

<p>Hydroboration follows the Anti-Markovnikov rule, while the addition of water follows Markovnikov's rule. (A)</p> Signup and view all the answers

What is the name of the process of adding an alkane to an alkene?

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

What is the product formed when a cis alkene is oxidized by cold alkaline KMnO4?

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

What is the product formed when propene reacts with HOCl?

<p>CH3CH2CH(OH)Cl (B)</p> Signup and view all the answers

Which of the following is NOT a characteristic of alkynes?

<p>They are typically more stable than alkanes. (B)</p> Signup and view all the answers

What is the product formed when an alkene undergoes allylic bromination using NBS?

<p>An alkene with a bromine atom at the allylic carbon. (C)</p> Signup and view all the answers

What is the best method to achieve chlorination of alkenes?

<p>Reaction with chlorine gas in liquid phase. (A)</p> Signup and view all the answers

Based on the given information, which of the following explains why alkene with the lowest heat of hydrogenation is the most stable?

<p>Higher heat of hydrogenation usually means that the alkene is less stable. (C)</p> Signup and view all the answers

What is the main product (A) formed when cis-but-2-ene reacts with alkaline KMnO4?

<p>Meso-1, 2-butan-di-ol (A)</p> Signup and view all the answers

Consider the reaction of an alkene with ozone followed by a reductive workup. What are the expected products X and Y for the alkene CH3-CH=CH-CH3?

<p>CH3-COOH (2 moles) (C)</p> Signup and view all the answers

What is the most likely intermediate formed in the reaction of propene with HOCl?

<p>CH3-CHCl-CH2+ (B)</p> Signup and view all the answers

What is the general formula for alkenes?

<p>C_nH_2n (A)</p> Signup and view all the answers

Which of the following is NOT a structural isomer of butene?

<p>CH_3 - CH_2 - CH_2 - CH_3 (A)</p> Signup and view all the answers

What is the main product formed when 2-bromobutane undergoes dehydrohalogenation in the presence of alcoholic KOH?

<p>But-2-ene (C)</p> Signup and view all the answers

Which of the following is NOT an example of an elimination reaction?

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

Why is cis-but-2-ene considered a stereoisomer of trans-but-2-ene?

<p>They have the same molecular formula but different spatial arrangements. (A)</p> Signup and view all the answers

What is the order of reactivity of alkyl halides in dehydrohalogenation?

<p>Tertiary &gt; secondary &gt; primary (D)</p> Signup and view all the answers

Which of the following statements regarding alkene preparation is TRUE?

<p>Dehydrohalogenation of an alkyl halide with alcoholic KOH can produce multiple alkene isomers. (D)</p> Signup and view all the answers

In the reaction of a free radical with an alkane, the major product is formed by attack at the

<p>tertiary carbon. (A)</p> Signup and view all the answers

What is the product formed when acetylene is oxidized with acidic KMnO4?

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

What is the name of the compound that forms when acetylene reacts with sodium in liquid ammonia?

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

What type of reaction is the reaction of acetylene with ammonical cuprous chloride?

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

Which of the following is NOT a product of the oxymercuration reaction of 1-butyne?

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

Which reagent can be used to distinguish between acetylene and ethane?

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

What is the main characteristic that makes the hydrogen atom in alkynes acidic?

<p>The hybridization of the carbon atom in the triple bond (A)</p> Signup and view all the answers

Which of the following statements is true about the oxidation of alkynes with K2Cr2O7 in acidic medium?

<p>It always forms carboxylic acids. (D)</p> Signup and view all the answers

Which of the following statements is true about the reaction of acetylene with sodium amide (NaNH2)?

<p>It forms a disodium acetylide. (B)</p> Signup and view all the answers

Flashcards

Major Product 'X'

Generated from the reaction of a free radical with an alkane, the most stable product.

Boiling Point Order

n-hexane has the highest boiling point compared to other alkanes.

Halogen Reactivity

Reactivity order of halogens with alkanes is F2 > Cl2 > Br2 > I2.

Propane from Propene

Propane can be obtained from propene through catalytic hydrogenation.

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Alkenes

Unsaturated hydrocarbons with a double bond, general formula CnH2n.

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Structural Isomerism in Butene

Butene has three structural isomers, differing in arrangement of atoms.

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Geometric Isomers of But-2-ene

Cis and trans forms exist due to hindered rotation around the C-C bond.

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Saytzeff’s Rule

In dehydrohalogenation, the major product is the most substituted alkene.

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Nitration

Introduction of the nitro group (NO2) into alkanes.

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Sulphonation

The process of adding a sulfonic acid group (–SO3H) to alkanes.

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Oxidation of alkanes

Alkanes react with oxygen to produce CO2 and H2O, releasing heat.

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Dehydrohalogenation

A reaction that removes hydrogen halide from vicinal dihalides to form alkenes.

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Reactivity of halogens

Order of reactivity: F2 > Cl2 > Br2 > I2.

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Kolbe’s Electrolysis

Electrolysis of dicarboxylic acid salts yields alkenes at the anode.

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Halogenation of alkanes

Addition of halogens to alkanes through radical substitution.

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Trans vs. Cis Alkenes

Trans isomers have higher melting points than cis due to better symmetry.

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Products of propane nitration

Nitration of propane yields various nitro-substituted products.

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Boiling Point of Alkenes

Cis isomers have higher boiling points due to greater dipole moment and polarity.

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Complete combustion equation for methane

CH4 + 2O2 → CO2 + 2H2O.

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Electrophilic Addition

Reactions of alkenes involving the addition of electrophiles across double bonds.

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Hexanesulphonic acid

Product formed from the sulphonation of hexane.

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Markovnikov’s Rule

Addition of hydrogen halides to unsymmetrical alkenes follows this rule for product formation.

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Anti-Markovnikov’s Rule

Addition of HBr in presence of peroxide yields products opposite to Markovnikov’s expectation.

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Addition Reactions of Alkenes

Includes hydrogenation, halogenation, and hydrogen halide reactions to create larger molecules.

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Alkyl Hydrogen Sulphates

Water soluble compounds derived from sulfuric acid and alkenes that convert to olefins upon heating.

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Markovnikov's Rule

When adding water to alkenes, the hydrogen atom attaches to the carbon with more hydrogen atoms.

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Hydroboration

Addition of diborane to alkenes that leads to Anti Markovnikov products.

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Oxymercuration-Demercuration

A two-step process for hydrating alkenes that avoids rearrangement and follows Markovnikov's rule.

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Oxidation by KMnO4

A reaction that detects double bonds in alkenes, producing syn-diol products.

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Ozonolysis

The reaction of alkenes with ozone to form carbonyl compounds.

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Hydroxylation by OsO4

An oxidative reaction adding OH groups to alkenes syn-fashion, producing glycols.

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Acetic Acid Addition

Addition to alkenes occurring trans, with cis giving racemic mixtures and trans yielding meso compounds.

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Chlorination

The reaction of alkenes with chlorine or carbon tetrachloride.

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Allylic Bromination

Bromination at the allylic carbon atom using N-bromosuccinimide (NBS).

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Heat of Hydrogenation

The heat change when hydrogen is added to an alkene.

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Syn Addition

The addition of two groups on the same side of a double bond.

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Anti Addition

The addition of two groups on opposite sides of a double bond.

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Meso Compound

A compound that has multiple chiral centers but is achiral due to symmetry.

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General Formula of Alkyne

The formula CnH2n−2 represents alkynes.

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Alkynes Characteristics

Alkynes are hydrocarbons with at least one triple bond.

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KMnO4 Oxidation

Oxidation of acetylene (HC≡CH) with KMnO4 leads to oxalic acid (HOOC−COOH).

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K2Cr2O7 Oxidation

Using potassium dichromate (K2Cr2O7) to oxidize acetylene forms acetic acid (CH3COOH).

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Acetylides Formation

Acetylides are formed when the acidic hydrogen of an alkyne is replaced by a metal.

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Sodium Acetylide

Formation of sodium acetylide occurs by the reaction of acetylene with sodium in liquid ammonia.

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Copper Acetylide

Copper acetylide is formed by the reaction of acetylene with copper(II) chloride in the presence of ammonium hydroxide to yield red precipitate.

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Silver Acetylide

Silver acetylide forms when acetylene reacts with silver nitrate in ammonium hydroxide, resulting in a white precipitate.

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Oxymercuration of 1-Butyne

A reaction where 1-butyne is treated with HgSO4 and H2SO4 to form a product, commonly used in organic synthesis.

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Study Notes

Alkanes

  • Alkanes are the simplest saturated hydrocarbons, also called paraffins.
  • Their general formula is CnH2n+2.
  • Carbon atoms in alkanes are sp³ hybridized.
  • They have a tetrahedral shape.
  • The bond length between C-H is 1.124 Ã….
  • The bond length between C-C is 1.544 Ã….
  • Methane (CHâ‚„) is the simplest alkane.

Conformation

  • Alkanes have various conformers due to free rotation around C-C single bonds.
  • Different spatial arrangements of atoms lead to conformers or rotamers.
  • Ethane has two types of conformations: staggered and eclipsed.
  • Staggered conformation is more stable than eclipsed due to less steric hindrance.

Methods of Preparation

  • Catalytic hydrogenation of unsaturated hydrocarbons: Adding hydrogen to unsaturated hydrocarbons in the presence of a catalyst (e.g., nickel, 200-300°C, or Raney Ni) for reduction.

  • Reduction of alkyl halides: Using a reducing agent in the presence of a catalyst such as Zn + CH3COOH, Zn + HCl, Zn + NaOH, Zn + Cu along with an alcohol (Câ‚‚Hâ‚…OH) or aluminum amalgam, or LiAlHâ‚„, to reduce alkyl halides.

  • Reduction of alcohols, aldehydes, and ketones: Reducing these compounds with hot hydroiodic acid (HI) and red phosphorus (P) at 150°C in a sealed tube to produce alkanes.

Physical Properties

  • Alkanes are colorless and odorless gases, liquids, or solids depending on molecular mass.
  • Density increases with increasing molecular mass.
  • They are insoluble in polar solvents (like water) but soluble in nonpolar solvents (like ether, CClâ‚„, benzene).
  • Boiling and melting points increase with increasing molecular mass but this isn't always smooth for alkanes.

Chemical Properties

  • Alkanes are relatively unreactive due to strong C-C and C-H bonds under normal conditions.

  • Halogenation (free radical substitution): Alkanes react with halogens (Clâ‚‚, Brâ‚‚) in the presence of light or high temperatures to form halogenated alkanes.

  • Other reactions (at high temperatures): Alkanes can undergo nitration, sulphonation, oxidation, etc

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