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Hydrocarbons question

2024 · 30 Jan · Shift 1 · Q6
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Hydrocarbons question

2024 · 30 Jan · Shift 1 · Q6

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Compound A formed in the following reaction reacts with B gives the product C. Find out A and B. JEE Main 2024 (Online) 30th January Morning Shift Chemistry - Hydrocarbons Question 30 English
  1. A
    A=CH3−C≡C−Na+,B=CH3−CH2−CH2−Br\mathrm{A}=\mathrm{CH}_3-\mathrm{C} \equiv \stackrel{-}{\mathrm{C}} \mathrm{Na}^{+}, \mathrm{B}=\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{Br}A=CH3​−C≡C−​Na+,B=CH3​−CH2​−CH2​−Br
  2. B
    A=CH3−CH=CH2, B=CH3−CH2−CH2−Br\mathrm{A}=\mathrm{CH}_3-\mathrm{CH}=\mathrm{CH}_2, \mathrm{~B}=\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{Br}A=CH3​−CH=CH2​, B=CH3​−CH2​−CH2​−Br
  3. C
    A=CH3−C≡C−Na+,B=CH3−CH2−CH3\mathrm{A}=\mathrm{CH}_3-\mathrm{C} \equiv \stackrel{-}{\mathrm{C}} \mathrm{Na}^{+}, \mathrm{B}=\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_3A=CH3​−C≡C−​Na+,B=CH3​−CH2​−CH3​
  4. D
    A=CH3−CH2−CH3, B=CH3−C≡CH\mathrm{A}=\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_3, \mathrm{~B}=\mathrm{CH}_3-\mathrm{C} \equiv \mathrm{CH}A=CH3​−CH2​−CH3​, B=CH3​−C≡CH
View written solutionFree

Correct answer: A

  1. Identify compound A formed in the reaction

    The reaction implied here is the formation of a sodium acetylide from a terminal alkyne. A terminal alkyne such as propyne, CH3−C≡CH\mathrm{CH_3-C\equiv CH}CH3​−C≡CH on treatment with a strong base like sodium amide gives CH3−C≡C− Na+\mathrm{CH_3-C\equiv C^-\ Na^+}CH3​−C≡C− Na+

    So the intermediate compound AAA should be the sodium salt of a terminal alkyne.

  2. Nature of reaction with B

    Sodium acetylides are strong nucleophiles and react with primary alkyl halides via SN2S_N2SN​2 reaction to form a higher alkyne.

    General reaction: R−C≡C− Na++R′−Br→R−C≡C−R′+NaBr\mathrm{R-C\equiv C^-\ Na^+ + R'-Br \rightarrow R-C\equiv C-R' + NaBr}R−C≡C− Na++R′−Br→R−C≡C−R′+NaBr

  3. Check the options

    Option A

    A=CH3−C≡C− Na+,B=CH3−CH2−CH2−BrA=\mathrm{CH_3-C\equiv C^-\ Na^+},\quad B=\mathrm{CH_3-CH_2-CH_2-Br}A=CH3​−C≡C− Na+,B=CH3​−CH2​−CH2​−Br Reaction: CH3−C≡C− Na++CH3CH2CH2Br→CH3−C≡C−CH2CH2CH3\mathrm{CH_3-C\equiv C^-\ Na^+ + CH_3CH_2CH_2Br \rightarrow CH_3-C\equiv C-CH_2CH_2CH_3}CH3​−C≡C− Na++CH3​CH2​CH2​Br→CH3​−C≡C−CH2​CH2​CH3​ This gives an internal alkyne, which is a standard alkylation of sodium acetylide with a primary alkyl bromide.

    So this is correct.

    Option B

    A=CH3−CH=CH2,B=CH3−CH2−CH2−BrA=\mathrm{CH_3-CH=CH_2},\quad B=\mathrm{CH_3-CH_2-CH_2-Br}A=CH3​−CH=CH2​,B=CH3​−CH2​−CH2​−Br Propene does not behave like an acetylide ion and will not undergo the required nucleophilic substitution to form the expected alkyne product.

    So this is incorrect.

    Option C

    A=CH3−C≡C− Na+,B=CH3−CH2−CH3A=\mathrm{CH_3-C\equiv C^-\ Na^+},\quad B=\mathrm{CH_3-CH_2-CH_3}A=CH3​−C≡C− Na+,B=CH3​−CH2​−CH3​ Propane is an alkane, not a good electrophile, and cannot react with sodium acetylide in this way.

    So this is incorrect.

    Option D

    A=CH3−CH2−CH3,B=CH3−C≡CHA=\mathrm{CH_3-CH_2-CH_3},\quad B=\mathrm{CH_3-C\equiv CH}A=CH3​−CH2​−CH3​,B=CH3​−C≡CH Propane is not the reactive intermediate formed, and terminal alkyne alone is not the electrophile for this coupling.

    So this is incorrect.

  4. Conclusion

    The only feasible pair is: A=CH3−C≡C− Na+,B=CH3−CH2−CH2−BrA=\mathrm{CH_3-C\equiv C^-\ Na^+},\quad B=\mathrm{CH_3-CH_2-CH_2-Br}A=CH3​−C≡C− Na+,B=CH3​−CH2​−CH2​−Br

    Hence, the correct option is A.

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