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कर्नाटक बोर्ड पी.यू.सी.पीयूसी विज्ञान 2nd PUC Class 12

How the following conversion can be carried out? Ethanol to propanenitrile - Chemistry

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प्रश्न

How do you convert the following:

Ethanol to propanenitrile

How the following conversion can be carried out?

Ethanol to propanenitrile

रासायनिक समीकरण/संरचनाएँ
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उत्तर १

\[\ce{\underset{Ethanol}{CH3 - CH2 - OH} ->[red P/Br2] \underset{Bromoethane}{CH3 - CH2 - Br} ->[KCN, aq.ethanol]\underset{Propanenitrile}{CH3 - CH2 - CN}}\]

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उत्तर २

\[\ce{\underset{Ethanol}{CH3CH2OH} ->[P/I2, \Delta] \underset{Iodoethane}{CH3CH2I} ->[KCN/EtOH-H2O][nucleophilic substitution] \underset{Propanenitrile}{CH3CH2CN}}\]

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Notes

Students can refer to the provided solutions based on their preferred marks.

  क्या इस प्रश्न या उत्तर में कोई त्रुटि है?
अध्याय 6: Haloalkanes and Haloarenes - Exercises [पृष्ठ १९१]

APPEARS IN

एनसीईआरटी Chemistry Part 1 and 2 [English] Class 12
अध्याय 6 Haloalkanes and Haloarenes
Exercises | Q 6.19 (vii) | पृष्ठ १९१

संबंधित प्रश्न

Discuss the mechanism of alkaline hydrolysis of bromomethane.


Write the structure of the major product in each of the following reaction :


In the following pair of halogen compounds, which compound undergoes a faster SN1 reaction?


Write the structure of the major organic product in the following reaction:

\[\ce{CH3CH(Br)CH2CH3 + NaOH ->[water]}\]


The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.


Answer the following question.
Write one stereochemical difference between SN1 and SN2 reactions.


In a coordination entity of the type [PtCl2(en)2]2+ which isomer will show optical isomerism?


Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of ____________.


Racemic compound has ____________.


Identify X and Y in the following sequence:

\[\ce{C2H5Br ->[X] Product ->[Y] C3H7NH2}\]


Assertion: KCN reacts with methyl chloride to give methyl isocyanide.

Reason: CN is an ambident nucleophile.


Complete the following analogy:

Same molecular formula but different structures: A : : Non superimposable mirror images: B


Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.


Chlorination of alkanes is an example of


In SN1 reactions, the correct order of reactivity for the following compounds:

CH3Cl, CH3CH2Cl, (CH3)2CHCl and (CH3)3CCl is ______.


Retention of configuration is observed in ______.


Convert bromoethane to propanamine.


The following questions are case-based questions. Read the passage carefully and answer the questions that follow:

Nucleophilic Substitution:
Nucleophilic substitution reaction of haloalkane can be conducted according to both SN1 and SN2 mechanisms. SN1 is a two-step reaction, while SN2 is a single-step reaction. For any haloalkane, which mechanism is followed depends on factors such as the structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent.

Influences of solvent polarity:
In SN1 reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating the reaction. In SN2 reaction, the polarity of the system generally does not change from the reactant to the transition state, and only charge dispersion occurs. At this time, the polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate (SN1) of tertiary chlorobutane at 25°C in water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24).

The reaction rate (SN2) of 2-bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has an influence on both SN1 and SN2 reactions but with different results. Generally speaking, a weak polar solvent is favourable for SN2 reaction, while a strong polar solvent is favourable for SN1. Generally speaking, the substitution reaction of tertiary haloalkane is based on SN1 mechanism in solvents with a strong polarity (for example ethanol containing water).

Answer the following questions:

(a) Why racemisation occurs in SN1? (1)

(b) Why is ethanol less polar than water? (1)

(c) Which one of, the following in each pair is more reactive towards SN2 reaction? (2)

(i) CH3 – CH2 – I or CH3CH2 – Cl

(ii)

OR

(c) Arrange the following in the increasing order of their reactivity towards SN1 reactions: (2)

(i) 2-Bromo-2-methylbutane, 1-Bromo-pentane, 2-Bromo-pentane

(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3- methylbutane


Discuss the mechanism of alkaline hydrolysis of methyl bromide.


Explain why Grignard reagents should be prepared under anhydrous conditions.


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