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Quiz20 Questions
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Quiz • 20 Questions

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Materials

List of Questions20 questions
  1. Question 1

    Which statement accurately describes the nuanced distinction between the reactivity orders of alcohols in hydrogen halide reactions and the reactivity order of alkyl halides in Finkelstein reactions, considering the underlying mechanistic principles?

    • Alcohol reactivity in H-X reactions follows an order ($3^\circ > 2^\circ > 1^\circ$) consistent with S$_N$1 pathway, involving carbocation stability, contrasting with alkyl halide reactivity (RI > RBr > RCl) in Finkelstein, which is governed by the superior nucleophilicity of iodide displacing weaker leaving groups via an S$_N$2 mechanism.
    • The reactivity of alcohols ($3^\circ > 2^\circ > 1^\circ$) in Grove's process mirrors the steric hindrance in S$_N$1-like bond scission, while alkyl halide reactivity (RI > RBr > RCl) in Finkelstein is governed by the leaving group ability of halides in nucleophilic substitution, favouring larger, more polarizable iodides.
    • The observed alcohol reactivity ($3^\circ > 2^\circ > 1^\circ$) in H-X reactions is primarily due to the electrophilic character of the hydroxyl oxygen, and Finkelstein reaction reactivity (RCl > RBr > RI) is exclusively influenced by the size of the attacking halide nucleophile.
    • Alcohol reactivity ($1^\circ > 2^\circ > 3^\circ$) in H-X reactions is due to inductive effects stabilizing carbocations, whereas alkyl halide reactivity (RF > RCl > RBr > RI) in Finkelstein reactions is dictated by the strength of the C-X bond, with stronger bonds leading to lower reactivity.
  2. Question 2

    The Darzen's process, utilizing thionyl chloride and an alcohol, is universally considered the most superior method for synthesizing all classes of alkyl halides (fluorides, chlorides, bromides, and iodides) due to its highly selective product formation and ease of byproduct removal.

    • True
    • False
  3. Question 3

    Elaborate on the mechanistic rationale behind the observed reactivity order ($1^\circ > 2^\circ > 3^\circ$) for the alkyl group in the Borodine-Hunsdiecker reaction and explain how this contrasts with typical S$_N$1 reactivity trends.

    • The Borodine-Hunsdiecker reaction proceeds via a free radical mechanism involving alkoxy radicals. The reactivity order ($1^\circ > 2^\circ > 3^\circ$) is observed because the primary alkyl radical, being less sterically hindered, is more readily formed and reacts faster in the propagation steps compared to more substituted radicals. This contrasts with S$_N$1 reactions, where reactivity follows $3^\circ > 2^\circ > 1^\circ$ due to the stability of carbocation intermediates.
  4. Question 4

    The oxidation of primary alkyl halides yielding aldehydes and secondary alkyl halides yielding ketones, either by Dimethyl Sulphoxide or Reaction with (CH$_2$)$_6$N$_4$ followed by hydrolysis, is fundamentally limited by the presence of ______ atoms relative to the halogen-bearing carbon.

    • alpha-hydrogen
  5. Question 5

    Match the following dihalide types with their defining structural characteristics:

  6. Question 6

    Consider the comprehensive reactivity hierarchy for alkyl halides: Polarity (RF > RCl > RBr > RI), Boiling Point (RI > RBr > RCl > RF), and General Reactivity (RI > RBr > RCl > RF). Which choice most profoundly explains why the trend in Polarity diverges from Boiling Point and General Reactivity?

    • The C-F bond's exceptional strength contributes to its low reactivity, and its strong dipole moment dominates polarity. In contrast, increasing atomic mass and polarizability down the halogen group lead to stronger London dispersion forces for higher boiling points and weaker C-X bonds that are more susceptible to cleavage, thus higher reactivity.
    • The disparity arises because polarity is an intrinsic molecular property dependent solely on atomic electronegativity, while boiling point is a colligative property governed by intermolecular forces, and reactivity is determined by the reaction's activation energy and transition state stability.
    • Polarity is dominated by electronegativity differences and bond dipole moments, with fluorine being the most electronegative, whereas boiling point and general reactivity are primarily influenced by molecular weight and the stability of the C-X bond, respectively, reflecting van der Waals forces and bond dissociation energies.
    • Polarity reflects the transient instantaneous dipoles leading to London dispersion forces, which are the main contributors to boiling point, and reactivity is a direct consequence of the inductive effect of the halogen on the carbon atom.
  7. Question 7

    The Friedel-Crafts alkylation of benzene with alkyl halides exclusively exemplifies an electrophilic substitution reaction where the alkyl halide acts as the electrophile, universally undergoing this transformation without exception in its structure.

    • True
    • False
  8. Question 8

    Derive the underlying principle for predicting whether an alkane with an odd or even number of carbon atoms can be synthesized via the Wurtz reaction or the mixed Wurtz reaction, considering the combinatorial possibilities of alkyl radicals.

    • The Wurtz reaction, involving two identical alkyl halides (R-X), exclusively yields alkanes with an even number of carbon atoms derived from the dimerization of identical R radicals. The mixed Wurtz reaction, using two different alkyl halides (R-X and R'-X), can produce alkanes with odd or even carbon numbers, as it forms R-R, R-R', and R'-R', necessitating careful separation to isolate the desired odd-carbon product (R-R').
  9. Question 9

    The 'Williamson ether synthesis' reaction involving an alkyl halide and sodium alkoxide, R-X + NaOR' R-O-R' + NaX, is a quintessential example of an ______ reaction, particularly effective with primary alkyl halides for optimal yields.

    • S$_N$2
  10. Question 10

    Match the specific reducing conditions with the resulting alkane derivatives from a haloalkane:

  11. Question 11

    The industrial synthesis of carbon tetrachloride (CCl$_4$) from carbon disulfide (CS$_2$) involves an initial reaction with chlorine to form CCl$_4$ and sulphur monochloride (S$_2$Cl$_2$), followed by the disproportionation of S$_2$Cl$_2$ in the presence of CS$_2$. Which of the following statements most accurately captures the intricate balance of reagents and conditions necessary for high selectivity and yield in this industrial process?

    • Optimal CCl$_4$ yield necessitates a catalytic amount of iodine and iron dust at elevated temperatures ($500^\circ$C) to drive the initial chlorination, while the subsequent S$_2$Cl$_2$ reaction is an autonomous step without further catalytic intervention.
    • The primary role of iron dust and iodine at $500^\circ$C is to mitigate over-chlorination of the CS$_2$ to CSCl$_2$, thus enhancing CCl$_4$ selectivity, with excess S$_2$Cl$_2$ being recycled to maximize sulphur recovery.
    • High yield and selectivity for CCl$_4$ are achieved by carefully controlling the Cl$_2$:CS$_2$ ratio and temperature ($500^\circ$C) in the presence of iron dust and iodine, which collectively manage the free radical chlorination and concurrent disproportionation of S$_2$Cl$_2$ to ensure minimal formation of S$_2$O, and maximizing CCl$_4$ and elemental sulfur.
    • The equilibrium of the initial chlorination strongly favours product formation under anhydrous conditions, and the complete suppression of side reactions yielding thiophosgene requires meticulous temperature control throughout the process.
  12. Question 12

    Despite the polar nature of the carbon-halogen bond, alkyl halides are predominantly soluble in water due to their capacity to form strong hydrogen bonds with water molecules, thereby overcoming the cohesive forces within the water lattice.

    • True
    • False
  13. Question 13

    Explain the fundamental chemical principle differentiating the reaction of alkyl cyanides (R-CN) with KCN versus AgCN, leading to divergent product outcomes (nitriles vs. isonitriles), and specify the key mechanistic factors at play.

    • The key difference lies in the nature of the bonding in KCN and AgCN. KCN is predominantly ionic, releasing a cyanide anion (CN-) which is an ambident nucleophile. The carbon atom's lone pair is more accessible and less sterically hindered, leading to n-attack and the formation of alkyl nitriles (R-CN) via S$_N$2. AgCN, on the other hand, has significant covalent character, and the lone pair on nitrogen is more available for donation due to the silver-carbon bond's partial covalent nature, resulting in N-attack and the formation of alkyl isonitriles (R-N=C) as the major product.
  14. Question 14

    The 'Strecker reaction,' involving the reaction of an alkyl halide with sodium sulfite (Na$_2$SO$_3$), is a pivotal method for the synthesis of ______, vital intermediates in the production of detergents.

    • alkyl sodium sulphonate
  15. Question 15

    Match the Grignard reagent reactions with the class of alcohol produced from carbonyl compounds:

  16. Question 16

    In the reduction of polyhalogenated methanes (e.g., CHCl$_3$) by nascent hydrogen, the resulting product (e.g., CH$_4$ from CHCl$_3$) signifies a stepwise dehalogenation process. Which of the following precisely articulates the controlled application of varying equivalents of nascent hydrogen, and the specific reducing agents, to achieve distinct levels of reduction, from dichloromethane to methane?

    • The transformation from CHCl$_3$ involves $+2$H (Zn/HCl) to CH$_2$Cl$_2$, then $+4$H (Zn/HCl) to CH$_3$Cl, and finally $+6$H (Zn/H$_2$O) to CH$_4$, illustrating a cumulative and progressive hydrogenation.
    • The initial reduction of CHCl$_3$ to CH$_2$Cl$_2$ requires 2 hydrogen equivalents from Zn/HCl, followed by 2 more for subsequent reduction to CH$_3$Cl, and ultimately 2 additional equivalents from Zn/H$_2$O for methane, totaling 6 equivalents.
    • To selectively obtain CH$_2$Cl$_2$ from CHCl$_3$, one requires 2 equivalents of nascent hydrogen, while complete reduction to CH$_4$ would necessitate a precisely controlled 6 equivalents, typically generated from Zn/HCl or Zn/H$_2$O.
    • Each sequential dehalogenation step (CHCl$_3$ to CH$_2$Cl$_2$, then to CH$_3$Cl, then to CH$_4$) fundamentally requires the addition of precisely 2 equivalents of nascent hydrogen across each C-Cl bond, irrespective of the specific reducing agent used (Zn/HCl or Zn/H$_2$O), due to the stoichiometry of bond cleavage and hydrogen addition.
  17. Question 17

    The 'Reimer-Tiemann Formylation' using phenol and chloroform in alkaline medium predominantly yields salicylaldehyde, a reaction that mechanistically involves the formation of a dichlorocarbene intermediate as the effective electrophile.

    • True
    • False
  18. Question 18

    Propose a detailed explanation for why only bromo derivatives are typically obtained from the Silver Salt of Carboxylic Acid reaction (Borodine-Hunsdiecker reaction), considering the underlying radical mechanism and the relative stabilities and reactivities of halogen radicals.

    • The Borodine-Hunsdiecker reaction proceeds via a free radical mechanism involving alkoxy radicals and halogen radicals. While theoretically other halogens could participate, only bromo derivatives are reliably obtained. This is attributed to the optimal reactivity of bromine radicals; iodine radicals are too unreactive, making the back reaction (recombination) dominant, while chlorine radicals are too reactive and non-selective, leading to undesirable side reactions and polyhalogenation. Bromine offers the ideal balance for selective radical transfer and propagation.
  19. Question 19

    The inherent polarity of the carbon-halogen bond notwithstanding, alkyl halides exhibit insolubility in water primarily because they lack the ability to form ______ bonds with water molecules, a critical prerequisite for dissolution.

    • hydrogen
  20. Question 20

    Match the specific reaction conditions for dihalides with the expected product class:

List of Flashcards20 flashcards
  1. Card 1

    Alkyl Halide

    Organic compounds where a halogen atom (F, Br, Cl, I) is directly linked to a carbon atom.

    HintThink about a carbon chain with a halogen attached.Memory TipAlkyl: carbon chain, Halide: halogen
  2. Card 2

    Alkyl Halide General Formula

    The general formula for alkyl halides, where 'n' represents the number of carbon atoms and 'X' represents a halogen (F, Br, Cl, I).

    HintIt's CnH2n+1X. Remember 'n' is for carbon atoms.Memory TipCnH2n+1X: carbon, hydrogen, halogen
  3. Card 3

    Alkyl Halide Carbon Hybridization

    The hybridization state of the carbon atom in alkyl halides to which the halogen is attached.

    HintConsider the geometry of the carbon atom, it's tetrahedral.Memory Tipsp3: tetrahedral carbon
  4. Card 4

    Monohalides

    Alkyl halides with only one halogen atom.

    HintMono- means one.Memory TipMono: one halogen
  5. Card 5

    Dihalides

    Alkyl halides with two halogen atoms, including gem dihalide, vicinal dihalide, and alpha, omega dihalide.

    HintDi- means two.Memory TipDi: two halogens
  6. Card 6

    Trihalides

    Alkyl halides with three halogen atoms (e.g., CHCl3).

    HintTri- means three.Memory TipTri: three halogens
  7. Card 7

    Tetrahalides

    Alkyl halides with four halogen atoms (e.g., CCl4).

    HintTetra- means four, like carbon tetrachloride.Memory TipTetra: four halogens
  8. Card 8

    Polyhalides

    Alkyl halides with more than four halogen atoms.

    HintPoly- means many.Memory TipPoly: multiple halogens
  9. Card 9

    Halogenation of Alkanes

    A method to prepare alkyl halides by reacting alkanes with halogens via a free radical mechanism.

    HintThis reaction uses UV light (hν) to initiate the process.Memory TipAlkane + Halogen = Alkyl Halide
  10. Card 10

    From Alkene (Hydrohalogenation)

    A method to prepare alkyl halides by reacting alkenes with hydrogen halides (HX), also known as hydrohalogenation.

    HintThink addition reaction across a double bond.Memory TipAlkene + HX = Alkyl Halide
  11. Card 11

    From Alcohol (Using Dry H-X)

    A common method for preparing alkyl halides from alcohols using dry hydrogen halides (HX).

    HintThis reaction often uses a catalyst like anhydrous ZnCl2.Memory TipAlcohol + HX = Alkyl Halide
  12. Card 12

    Reactivity Order of HX

    The order of reactivity for hydrogen halides in reactions with alcohols: HI > HBr > HCl.

    HintThink about bond strength; weaker bonds react faster.Memory TipHI strongest, HCl weakest
  13. Card 13

    Grove's Process

    The reaction of alcohols with HCl in the presence of anhydrous ZnCl2, a specific method for preparing alkyl halides.

    HintThis process involves an acid and a zinc salt.Memory TipGrove's: alcohol to alkyl halide
  14. Card 14

    Darzen's Process

    A very good method for preparing alkyl halides using thionyl chloride (SOCl2) and pyridine.

    HintThis method produces gaseous side products (HCl and SO2), making purification easier.Memory TipDarzen's: SOCl2 + pyridine
  15. Card 15

    Borodine-Hunsdiecker Reaction

    A reaction where bromo derivatives of alkyl halides are obtained from silver salts of carboxylic acids, involving a free radical mechanism.

    HintThink about a carboxylic acid salt and bromine.Memory TipBorodine-Hunsdiecker: Bromo-derivatives
  16. Card 16

    Finkelstein Reaction

    A halogen exchange reaction where an alkyl chloride or bromide reacts with potassium iodide (KI) in acetone to form an alkyl iodide.

    HintIt swaps one halogen for another, specifically iodine.Memory TipFinkelstein: iodide exchange
  17. Card 17

    Swarts Reaction

    A halogen exchange reaction where an alkyl bromide or chloride reacts with metallic fluorides (like AgF) to form an alkyl fluoride.

    HintIt's the method to make fluorine-containing alkyl halides.Memory TipSwarts: fluoride exchange
  18. Card 18

    Physical State of Alkyl Halides

    Alkyl halides primarily exist as this state with a sweet or pleasant smell, but smaller ones can be gaseous.

    HintThink about their general appearance at room temperature.Memory TipOily liquid, sweet smell
  19. Card 19

    Insolubility in Water

    A property of alkyl halides, meaning the carbon-halogen bond is polar, but they generally don't mix with water.

    HintThey can't form hydrogen bonds with water molecules.Memory TipPolar, but no H-bond
  20. Card 20

    Reactivity Order of Alkyl Halides

    The reactivity order for alkyl halides with the same halide group: 3º halide > 2º halide > 1º halide.

    HintTertiary alkyl halides are generally more reactive.Memory Tip3 > 2 > 1 reactivity