Haloalkanes and Haloarenes Quiz
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Questions and Answers

Which of the following is NOT an example of an aryl halide?

  • (2) (correct)
  • (1)
  • (4)
  • (3)

Which statement about the given representations of haloalkanes and haloarenes is true?

  • (1) represents a vinylic halide.
  • (2) represents an allylic halide.
  • (3) represents a benzylic halide. (correct)
  • All of the above.

Which of the following represents 4-Bromo-3-methylpent-2-ene?

  • (3) (correct)
  • (4)
  • (2)
  • (1)

Which of the options contains ONLY secondary (2°) halides?

<p>a, c, and d (B)</p> Signup and view all the answers

Identify the compound from the options that is classified as a benzylic halide.

<p>(1) (A)</p> Signup and view all the answers

Which of the given structures represents a vinyl halide?

<p>(2) (A)</p> Signup and view all the answers

Which of the listed methods is NOT a suitable method for obtaining a halide?

<p>(3) (A)</p> Signup and view all the answers

Why is sulfuric acid not used during the reaction of alcohol with KI?

<p>I⁻ is a strong reducing agent, reducing H₂SO₄ to I₂. (D)</p> Signup and view all the answers

Which of the following alkyl halides is the most reactive towards an SN2 reaction?

<p>1 (B)</p> Signup and view all the answers

In the reaction Ph-CH(Cl)-Ph + H2O → Ph-CH(OH)-Ph, which statement is incorrect?

<p>The reaction is a bimolecular substitution. (A)</p> Signup and view all the answers

Which of these reactions demonstrates pure inversion of configuration?

<p>Reaction 1 (C)</p> Signup and view all the answers

Which alkyl halide, when heated with KOH, will produce only one alkene product?

<p>2-Bromo-2-methylpropane (D)</p> Signup and view all the answers

Which statement correctly describes the carbon-magnesium bond in a Grignard reagent?

<p>It is a highly polar covalent bond. (B)</p> Signup and view all the answers

Why are aryl halides generally less reactive than aliphatic halides towards nucleophilic substitution reactions (NSR)?

<p>The sp2 carbon of the ring holds the electron pair of the C–X bond more tightly. (B)</p> Signup and view all the answers

What is the major factor that influences the reactivity of alkyl halides in an SN2 reaction?

<p>The presence of bulky groups around the reaction center (C)</p> Signup and view all the answers

Which of the following is an example of a unimolecular nucleophilic substitution reaction (SN1)?

<p>Ph—CH—Ph + H2O → Ph—CH—Ph | | Cl OH (A)</p> Signup and view all the answers

Which statement about the bromination of (CH3)2CH–CH2–CH3 under light is incorrect?

<p>The reaction requires high temperatures (A)</p> Signup and view all the answers

Which reaction yields an aryl halide as the primary product?

<p>Reaction of benzene with $Cl_2$ in the presence of $FeCl_3$ (D)</p> Signup and view all the answers

Which reaction does NOT produce a cyanide as a major product?

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

Why does the reaction of a haloalkane with AgCN primarily yield an isocyanide instead of a cyanide?

<p>AgCN is mainly covalent, and the nitrogen atom is free to donate electron pair. (C)</p> Signup and view all the answers

Which of the following reactions is an example of racemization at a chiral center?

<p>$CH_3–CH(D)–Cl + OH^- \rightarrow$ (D)</p> Signup and view all the answers

Which statement about the reaction of haloarenes with nucleophiles is incorrect?

<p>The effect of electron-withdrawing groups is most effective when they are at the meta position. (C)</p> Signup and view all the answers

What is a correct statement about the oxidation of alcohols?

<p>Oxidation of secondary alcohols results in ketones. (B)</p> Signup and view all the answers

Regarding the influence of a nitro group (-NO2) on the stability of intermediate anions in nucleophilic substitution of haloarenes, which statement is correct?

<p>The -NO2 group at the ortho and para positions provides greater stability compared to the meta position. (D)</p> Signup and view all the answers

What is the major product of the reaction between (CH3)2CH–CH2–CH3 and $Br_2$ in the presence of light?

<p>$(CH_3)_2CH–CHBr–CH_3$ (C)</p> Signup and view all the answers

What is the correct relationship between the statements regarding the effect of -NO2 group?

<p>Both Statement I and Statement II are true. (C)</p> Signup and view all the answers

Which statement about the reaction between $Ph–CH_2–OH$ and NaCN is correct?

<p>No reaction will occur under normal conditions. (A)</p> Signup and view all the answers

In nitration of haloarenes, why is the major product a para-substituted isomer instead of a meta-substituted isomer despite chlorine being a deactivating group?

<p>The resonance effect (+M) of chlorine directs the incoming group to the para position, overwhelming the inductive effect. (A)</p> Signup and view all the answers

Which statement correctly describes the influence of inductive (-I) and resonance (+M ) effects in the nitration of haloarenes?

<p>The resonance effect (+M) of halogens dominates the inductive effect (-I), directing substitution to the ortho and para positions. (A)</p> Signup and view all the answers

Which statement regarding freons is false?

<p>Freons are only stable within the troposphere. (C)</p> Signup and view all the answers

Which of the following would be considered as a freon?

<p>$CCl_2F_2$ (D)</p> Signup and view all the answers

What is the primary function of freons in a typical application?

<p>To serve as a propellant in aerosol sprays and as a refrigerant (C)</p> Signup and view all the answers

What is the relationship between the presence of a -M group on a ring and the ease of nucleophilic substitution reactions (NSR)?

<p>A -M group facilitates nucleophilic attack, making NSR easier. (B)</p> Signup and view all the answers

Why is it crucial to prepare Grignard reagents under anhydrous conditions?

<p>Water reacts violently with Grignard reagents leading to their deactivation. (B)</p> Signup and view all the answers

What is the effect of CCl4 on the ozone layer?

<p>It contributes to the depletion of the ozone layer. (C)</p> Signup and view all the answers

Which of the following statements about alkyl halides and water is true?

<p>Alkyl halides are polar but immiscible with water. (D)</p> Signup and view all the answers

What is the main nucleophilic substitution product when n-Butyl bromide reacts with KCN?

<p>n-butyl cyanide (A)</p> Signup and view all the answers

Which statement accurately describes the conditions for nucleophilic substitution reaction (NSR) of haloarenes and 2,4,6-trinitro haloarenes?

<p>Haloarenes undergo NSR at high temperature, and 2,4,6-trinitro haloarenes undergo NSR at low temperature. (A)</p> Signup and view all the answers

How does CCl4 exposure affect the human body according to the text?

<p>It can cause irregular or stopped heartbeats. (B)</p> Signup and view all the answers

Which compound from the following is more readily hydrolyzed and why: C6H5–CHCl–C6H5 or C6H5–CH2–Cl?

<p>C6H5–CHCl–C6H5 is more readily hydrolyzed because the carbocation formed is more stable. (C)</p> Signup and view all the answers

Flashcards

What is an aryl halide?

An aryl halide is a halide attached directly to an aromatic ring. If the halide is attached to a carbon that is directly attached to an aromatic ring but NOT the aromatic ring itself, it is NOT an aryl halide.

What is a 2° halide?

A 2° halide is a halide attached to a carbon that is bonded to two other carbons. A 1° halide is attached to a carbon bonded to one other carbon. A 3° halide is attached to a carbon bonded to three other carbons.

What is a benzylic Halide?

A benzylic halide is a halide directly attached to the carbon atom adjacent to (but not part of) the aromatic ring.

What is a haloalkane?

A haloalkane is an alkane that has a halogen atom bonded to one of its carbons. A haloalkane is a hydrocarbon, making it a compound made up of only carbon and hydrogen atoms.

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What is a haloarene?

A haloarene is an aromatic compound where one or more of the hydrogen atoms on the aromatic ring have been replaced by halogen atoms.

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Why is sulfuric acid not used to react with alcohols and KI?

KI can react with alcohols to form alkyl iodides. However, sulfuric acid is a strong oxidizing agent and can react with iodide ions, oxidizing them to iodine and forming HI. This is why sulfuric acid is not used in the reaction of alcohols with KI because it can interfere with the reaction.

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Why is sulfuric acid not used to react with alcohols and KI (Dehydration)?

Alcohols can be dehydrated by strong acids, such as sulfuric acid, leading to the formation of alkenes. This can be unwanted side reaction, that's why sulfuric acid is not used to react with alcohols and KI.

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Why are SN1 reactions favored by tertiary halides?

SN1 reactions are favored by tertiary halides. This is because the carbocation intermediate formed in the reaction is more stable for tertiary halides. The tertiary carbocation is more stable due to hyperconjugation. The carbocation intermediate is formed in the first step of an SN1 reaction.

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Free Radical Substitution

The process involves the substitution of a hydrogen atom in an alkane with a bromine atom using light as a catalyst.

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Alkyl Halide

An alkyl halide is a compound where a halogen atom is bonded to a saturated carbon atom. It can be primary, secondary, or tertiary depending on the number of carbon atoms attached to the carbon atom bearing the halogen.

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Aryl Halide

An aryl halide is a compound where a halogen atom is bonded to a carbon atom in an aromatic ring. The halogen atom is attached to a carbon atom of the ring, making it a part of the aromatic system.

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Nucleophilic Substitution with Cyanide

The nucleophilic substitution reaction that occurs when a haloalkane reacts with a cyanide ion (CN-), resulting in the formation of a nitrile.

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Reaction of Haloalkane with Silver Cyanide

When a haloalkane reacts with silver cyanide, it gives an isocyanide as the major product.

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Racemization

A molecule that exists in two mirror-image forms (enantiomers) and the conversion of one enantiomer to the other.

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Racemization: How it Occurs

It occurs when a chiral molecule undergoes a reaction that breaks and reforms a bond at a chiral center.

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What is the key feature of the reaction rate in the provided reaction?

The rate of the reaction is only dependent on the halide concentration, meaning it's a unimolecular reaction.

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Does the provided reaction always result in a complete inversion of configuration?

The reaction proceeds through a carbocation intermediate, which allows for the possibility of both inversion and retention of configuration.

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What type of mechanism is exemplified by a reaction with pure inversion?

The reaction proceeds with a complete inversion of configuration, meaning the nucleophile attacks from the opposite side of the leaving group.

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Why are aryl halides less reactive than aliphatic halides towards NSR?

Aryl halides are less reactive towards nucleophilic substitution reactions (NSR) due to the resonance effect, which stabilizes the carbon-halogen bond and makes it less susceptible to nucleophilic attack.

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Which of the given compounds can produce only one alkene upon heating with KOH?

2-Bromo-2-methyl propane will only produce one alkene upon elimination because all hydrogen atoms on the beta-carbon are equivalent.

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What is the nature of the carbon-magnesium bond in a Grignard reagent?

The carbon-magnesium bond in a Grignard reagent is highly polar, with significant ionic character.

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What is the major product formed when a Grignard reagent reacts with ethyl chloride?

The Grignard reagent reacts with ethyl chloride to give ethane. The Grignard reagent can be used to add a carbon chain to another molecule.

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What is a nucleophilic substitution reaction?

A nucleophilic substitution reaction is a reaction where a nucleophile (an electron-rich species) attacks an electrophilic carbon atom, replacing a leaving group.

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Why is the major product in haloarene nitration para-nitro haloarene, not meta-nitro haloarene?

Strong electron withdrawing groups like nitro groups can be deactivated groups. However, in the nitration of haloarenes, the major product is para-nitro haloarene, not meta-nitro haloarene.

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Why are halogens deactivating groups in electrophilic aromatic substitution?

The stronger inductive effect (-I) of halogens compared to their resonance effect (+M) makes them deactivating groups in electrophilic aromatic substitution. However, the ortho and para positions are more reactive due to resonance stabilization.

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How does the presence of electron-withdrawing groups (EWGs) affect the reactivity of haloarenes?

The presence of electron-withdrawing groups (EWGs) like nitro groups in haloarenes increases their reactivity towards electrophilic aromatic substitution due to the stabilization of the intermediate carbocation.

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How do freons damage the ozone layer?

Free radicals are highly reactive species with unpaired electrons. In the troposphere, freons can absorb UV radiation and break down into free radicals, which can deplete the ozone layer.

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What are Freons and why are they harmful?

Freons are chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) used as refrigerants and propellants. They have a high chemical stability, are non-toxic, and non-corrosive. However, they have harmful environmental effects by depleting the ozone layer in the stratosphere.

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Why does the nitro group at ortho and para positions increase the rate of nucleophilic substitution in haloarenes?

The stability of the intermediate anion is higher when the nitro group is at the ortho or para position compared to the meta position, leading to an increased rate of nucleophilic substitution at ortho and para positions.

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How does the resonance effect of the nitro group influence nucleophilic substitution in haloarenes?

The resonance effect of the nitro group is significant at ortho and para positions, but not at the meta position. This explains the increased reactivity towards nucleophilic substitution at ortho and para positions.

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What is a radical chain reaction?

A chemical reaction where a chain of reactions involving free radicals propagates itself. These reactions are important in atmospheric chemistry, where free radicals can cause the depletion of the ozone layer.

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How can CCl4 affect the ozone layer?

CCl4, also known as carbon tetrachloride, is a chlorofluorocarbon (CFC) that can cause the depletion of the ozone layer. CFCs release chlorine atoms into the atmosphere, which break down ozone molecules (O3) into oxygen (O2) and chlorine monoxide (ClO).

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What are haloarenes?

Haloarenes are aromatic compounds (containing a benzene ring) with a halogen atom directly attached to the ring. Haloarenes are relatively unreactive, but they can undergo electrophilic aromatic substitution reactions.

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Why is EAS slower in haloarenes?

The electrophilic aromatic substitution (EAS) reaction of haloarenes occurs at a slower rate compared to benzene. This is because the halogen substituent exerts an electron-withdrawing effect, making the aromatic ring less electron-rich and less reactive towards electrophiles.

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Are haloarenes reactive to nucleophiles?

The assertion that haloarenes exhibit nucleophilic substitution reactions (NSR) at high temperatures is true. The reason for this is that at high temperatures, the carbon-halogen bond in the haloarene weakens, making it more susceptible to nucleophilic attack.

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Why are Grignard reagents prepared under anhydrous conditions?

Grignard reagents are extremely reactive and must be prepared in anhydrous conditions. They are organometallic compounds containing a carbon-metal bond, specifically magnesium. The presence of water would react with the Grignard reagent, destroying its reactivity.

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What is the product of reaction of sec-butyl bromide with KCN?

Secondary butyl bromide reacts with KCN via an SN2 reaction to form secondary butyl cyanide. The reaction proceeds through a backside attack of the cyanide ion on the carbon atom bonded to the bromide.

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Why are tertiary alkyl halides more reactive in SN1 reactions?

Tertiary alkyl halides are more prone to undergo SN1 reactions compared to primary or secondary alkyl halides. This is due to the stability of the tertiary carbocation intermediate formed in the SN1 reaction.

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Study Notes

Haloalkanes and Haloarenes

  • Question 1: Which is not an aryl halide?

    • Option 3 is the correct answer.
  • Question 2: Which is a true statement?

    • Option 1 is correct: X is an allylic halide. Option 2 is correct: X is a vinylic halide. Option 3 is correct: X is a benzylic halide. Option 4 is implied as a correct option.
  • Question 4: Which halide is secondary? (More than one answer)

    • Option a: CH2=CH-CH-Cl is a secondary halide.
    • Option c: Ph-CH-Ph is a secondary halide.
    • Option d: A structure (drawn) is a secondary halide.
    • Option e: A structure (drawn) is a secondary halide.
  • Question 5: What is the major product of the reaction CH2=C=CH2 + HBr Peroxide?

    • Option 1 is the correct answer.
  • Question 6: What is the product of the reaction? (with appropriate structure)

    • Option 3 (with structure) is the correct answer.
  • Question 7: Which method is incorrect to obtain a halide?

    • Option 1 is not a correct method.
  • Question 8: Why is H2SO4 not used with alcohols and KI?

    • I- is a strong reducing agent, reducing H2SO4 into I2.
  • Question 9: Incorrect statement about reaction (CH3)2CHCH2CH3 + Br2 --> (with structure)?

    • Option 1 is incorrect: The major product is (CH3)2CBrCH2CH3.
  • Question 10: Which reaction gives an aryl halide as a major product?

    • Option 1: Aryl halide (with structure).
  • Question 11: Major product in reaction (with structure) is what?

    • Option 1 (with structure).
  • Question 12: Major product in reaction with structure?

    • Option 4 (with structure).
  • Question 13: Missing reaction and options.

  • Question 14: Reaction that does not give cyanide (with structures).

    • Option 3 (with structure)is incorrect.
  • Question 15: Reaction of haloalkane with AgCN gives isocyanide as major product due to...

    • AgCN is mainly covalent and carbon is free to donate electron pairs.
  • Question 16: Most reactive towards SN2?

    • Option 1 (with applicable structure).
  • Question 17: Incorrect statement in the following reaction (with structure)?

    • Option 2 (incorrect statement).
  • Question 18: Example of pure inversion?

    • Option 3 (with structure).
  • Question 19: Example of racemization reaction?

    • Option 4 (with structure).
  • Question 20: Reaction of alkene with structure (with product structures)?

    • Option 1 (with structure) is the correct answer.
  • Question 21: Which alkene can result in only one alkene when heated with KOH?

    • Option 2: 2-Bromo-2-methyl propane.
  • Question 22: Correct statement about Grignard reagents?

    • Option 2: Carbon-magnesium bond is an ionic bond.
  • Question 23: Why is aryl halide less reactive (than aliphatic) in nucleophilic substitution reactions?

    • Electron pairs on halogen conjugate with ring bonds.
  • Question 24: Incorrect statement about reaction? (with structure)

    • Option 3 is incorrect.
  • Question 25: Statement I and II regarding nucleophilic substitution in haloarenes.

    • Statement I is true, but Statement II is false.
  • Question 26: Assertion and Reason about haloarenes giving nucleophilic substitution reactions.

    • Both Assertion and Reason are true, but Reason is not a correct explanation.
  • Question 27: Assertion and Reason about chlorination of haloarenes.

    • Assertion is true but Reason is false.
  • Question 28: False statement about Freons.

    • Option 4 is false: In troposphere, freon does not initiate radical chain reactions.
  • Question 29: Statement I and II regarding ozone depletion by CCl4.

    • Statement I is false, but Statement II is true.
  • Question 30: Incorrect statement(s)?

    • Option 4 is incorrect - alkyl halides are polar and miscible with water. (emphasis on miscible)

Answer Key (from the provided image)

  • A table of answers is provided after the questions. Directly refer to the table for specific answers to each question.

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Haloalkanes and Haloarenes PDF

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Test your knowledge on haloalkanes and haloarenes with this quiz. Answer questions about aryl halides, allylic and vinylic halides, and secondary halides. Challenge yourself to identify reaction products and methods for obtaining halides.

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