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Chemistry Test - 15
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Chemistry Test - 15
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  • Question 1/10
    5 / -1

    Select the incorrect statement (s) about the following reaction of ether synthesis.

    RX + R' ONa  RO R' + NaX

    Solutions

    Explanation-

    Ether synthesis-

    The general method for the synthesis of ether is Williamson ether synthesis, involves nucleophilic displacement of a halide ion or other good leaving group by an alkoxide ion.

    The name of the reaction was coined after Alexander William Williamson developed it in 1850. Williamson Ether Synthesis is a reaction that uses deprotonated alcohol and an organohalide to form an ether.

    • Williamson Ether Synthesis usually takes place as an SN2 reaction of a primary alkyl halide with a 2° or 3° alkoxide ion. The structure of ethers was proved due to this chemical reaction.
    • SN2 pathway is required for the synthesis of this reaction and is useful only when the alkyl halide is primary or secondary.
    • The Ethers produced in this way have more carbon atoms than either of the starting materials and thus are more complex structures.
    • 2° and 3° alkyl halides may undergo E2 elimination in the presence of a strong base to form alkenes.

    Mechanism of this reaction-

    • The nucleophile attacks the alkyl halide forming an ether from the back.
    • This response takes place in a single step, which is both cleavage and bond formation.
    • If halides are sterically impeded then alkoxide acts as a basis and protons in β-place are accessible.
    • The products are derived from a response to elimination.

  • Question 2/10
    5 / -1

    In the reaction,

    2A + dry silver oxide Δ ether + 2 AgX, A is a/an

    Solutions

    Explanation:

    Given:

    ⇒ 2A+ Dry Silver Oxide  Δ  R-O-R (ether) + 2AgX 

    We know,

    An alkyl Halide on heating with dry silver oxide gives ether

    ⇒ 2 R - X + Ag2Δ R - O - R + 2 AgX

  • Question 3/10
    5 / -1

    Which of the following will undergo Friedel - Craft's alkylation reaction?

    Solutions

    Explanation-

    Friedel-Crafts Alkylation-

    It refers to the replacement of an aromatic proton with an alkyl group. This is done through an electrophilic attack on the aromatic ring with the help of a carbocation. The Friedel-Crafts alkylation reaction is a method of generating alkylbenzenes by using alkyl halides as reactants.

    The Friedel-Crafts alkylation reaction of benzene is illustrated below.

    A Lewis acid catalyst such as FeCl3 or AlCl3 is employed in this reaction in order to form a carbocation by facilitating the removal of the halide. The resulting carbocation undergoes a rearrangement before proceeding with the alkylation reaction.

    Some important limitations of Friedel-Crafts alkylation are listed below-

    • Since the carbocations formed by aryl and vinyl halides are extremely unstable, they cannot be used in this reaction.
    • The presence of a deactivating group on the aromatic ring (such as an NH2 group) can lead to the deactivation of the catalyst due to the formation of complexes.
    • An excess of the aromatic compound must be used in these reactions in order to avoid polyalkylation (addition of more than one alkyl group to the aromatic compound).
    • Aromatic compounds that are less reactive than mono-halobenzenes do not participate in the Friedel-Crafts alkylation reaction.

     

    Friedel craft alkylation will undergo by that aromatic compound, which is electron-rich. As it is the electrophilic substitution reaction.

    So both 2 and 4 will undergo  Friedel - Craft's alkylation reaction.

  • Question 4/10
    5 / -1

    Which of the following is obtained on treating phenol with conc. HNO3 / H2SO4 mixture?
    Solutions

    Explanation-

    Phenol is an aromatic alcohol. We know aromatic compounds easily give electrophilic substitution reactions.

    Electrophilic substitution reactions are the reactions in which an electrophile replaces a functional group generally a proton from the reactant.

    Concentrated  is concentrated nitric acid. It is a nitrating reagent.

    Phenol will undergo a nitration reaction in the presence of concentrated. nitric acid,  to give 2, 4, 6-trinitrophenol which is also known as picric acid.

    Phenol will undergo nitration in presence of nitric acid also but will form either mono- or di-substituted ortho- or para-nitrophenols.

    Phenols are nucleophilic in nature and hence undergo electrophilic substitution reactions like nitration, sulphonation, alkylation, acetylation, and halogenation.

     

     will be formed on treating phenol with concentrated HNO3 / H2SO4 mixture.

     

  • Question 5/10
    5 / -1

    Which of the following is most acidic?
    Solutions

    Explanation:

    → The phenoxide ions left from o-hydroxybenzaldehyde and p-hydroxybenzaldehyde are stabilized by the-I and R-effect of the -CHO group.

    → But due to chelation in the o-isomer, it is difficult to remove the H-atom.

    Hence, p-hydroxybenzaldehyde is the strongest acid.

    Important Points→ Acidity of a compound depends on the nature of groups presented on that compound. As we can say –I (Inductive effect) and +R (Resonance effect) increase the acidity whereas the +I effect increases the basicity. 

  • Question 6/10
    5 / -1

    Which of the following has highest dipole moment?
    Solutions

    Explanation:

    → o - Isomer has a maximum dipole moment.

    Additional Information→ Due to intramolecular hydrogen bonding, derivatives of phenol, i.e. o-nitrophenol has a lower solubility in water, and lower boiling point.

    → Due to this, association with different molecules decreases hence, comparatively volatile in nature. On the other hand, m and p- isomer have intermolecular hydrogen bonding.

    Thus, they have an appreciable value of boiling point and are soluble in water.

    Isomer

    Boiling
    point at 760 mm

    Solubility
    g/100g H2O

     
    o-nitrophenol373 K0.2volatile in steam
    p-nitrophenoldecomposes1.69non-volatile in steam
    m-nitrophenol467 K1.35non-volatile in steam

     

  • Question 7/10
    5 / -1

    Phenol 

    Name of the reaction is

    Solutions

    Explanation-

    Liebermann's reaction -

    When phenol is reacted with NaNO2 and concentrated H2SO4, it provides a deep green or blue color which changes to red on dilution with water. Generated substance in presence of NaOH / KOH restores the original green or blue color. This reaction is termed as Liebermann's nitroso reaction.

    Other Important Points-

    Reimer - Tiemann reaction-

    Reimer Tiemann reaction is a type of substitution reaction, named after chemists Karl Reimer and Ferdinand Tiemann. The reaction is used for the ortho-formylation of C6H5OH (phenols).

    Schotten - Baumann reaction-

    Schotten Baumann reaction refers to the method of chemically synthesizing amides from acyl chlorides and amines. This organic chemical reaction is named after the German chemist Carl Schotten and Eugen Baumann, who discovered this method of synthesizing amides.

  • Question 8/10
    5 / -1

    The IUPAC name of the following compound is:

      

    Solutions

    Explanation:

    1.  IUPAC name is the name that follows the chemistry rules for naming a compound.
    2. In IUPAC naming, the organic compounds are named after the parent hydrocarbon by using certain prefixes or suffixes to indicate the presence of a functional group

    In the above molecule, it is an ether ROR′. The substituent name for the  RO−  function is alkoxy, and it is correct to name  R−O−R′  compounds as alkoxy derivatives of hydrocarbons.

    The longest chain of carbons contains 3 carbons so it becomes prop and single bond so ane. The methoxy group is in 2nd position.

    Thus its name is: 2 - methoxypropane

  • Question 9/10
    5 / -1

    Phenol on treatment with diethyl sulphate in presence of NaOH gives
    Solutions

    Explanation:

    Diethyl sulphate in the presence of NaOH acts as an alkylating agent, it causes the alkylation of phenol to give ethyl phenyl ether which is also called phenetole.

    → C6H5OH + NaOH → C6 H5 O Na+ + H2O

    → C6 HO Na+ + C2H5SO4 (diethyl sulphate) →  C6H5OC2H5 (phenetole) + C2H5NaSO4

  • Question 10/10
    5 / -1

    Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI?
    Solutions

    Explanation-

    The reaction of ether with the strong hydriodic acid (HI), causes the cleavage of the ether C-O bond, following the nucleophilic substitution reaction.

    This cleavage further depends on the degree of alkyl group present in the ether as the primary and the secondary alkyl ethers have less steric hindrance. Thus, it shows the  mechanism.

    In the primary and the secondary alkyl ethers, following the mechanism, due to less hindrance, the iodide attaches to the smaller alkyl group, whereas in the tertiary alkyl ether following the  mechanism, the high stability of the tertiary carbocation the iodide attaches to it, and the smaller alkyl forms the alcohol.

    Option 1-

    So, in  CH3 - CH- CH2 - CH2 - O - CH3, through the  mechanism, having  alkyl group, on reaction with HI, it forms butanol and methyl iodide.

    Option 2-

    In   , having a  alkyl group, on reaction it forms methyl iodide and isobutyl alcohol.

    Option 3-

    In the case of the tertiary alkyl ether due to steric hindrance, it follows the  mechanism through the formation of the stable carbocation intermediate. So, in the compound given in option 3, on reaction we get tertiary- butyl iodide and methanol. As follows:

    Option 4-

     In reaction with HI, it forms 2-methyl propanol and methyl iodide.

    So option 3 is the correct answer.

     

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