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Chemistry
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Complete the reaction with the main product formed:

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

Convert bromoethane to propanamine.

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

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Give the mechanism of the following reaction:

\[\ce{CH3CH2OH ->[H2SO4][413 K] CH3CH2-O-CH2CH3 + H2O}\]

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

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

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

An organic compound 'A' with molecular formula C5H8O2 is reduced to n-pentane with hydrazine followed by heating with NaOH and glycol. 'A' forms a dioxime with hydroxylamine and gives a positive iodoform and Tollen's test. Identify 'A' and give its reaction for iodoform and Tollen's test.

[8] Aldehydes, Ketones and Carboxylic Acids
Chapter: [8] Aldehydes, Ketones and Carboxylic Acids
Concept: undefined >> undefined

An organic compound 'A' with the molecular formula C4H8O2 undergoes acid hydrolysis to form two compounds 'B' and 'C'. Oxidation of 'C' with acidified potassium permanganate also produces 'B'. Sodium salt of 'B' on heating with soda lime gives methane.

  1. Identify 'A', 'B' and 'C'.
  2. Out of 'B' and 'C', which will have higher boiling point? Give reason.
[8] Aldehydes, Ketones and Carboxylic Acids
Chapter: [8] Aldehydes, Ketones and Carboxylic Acids
Concept: undefined >> undefined

Hydrolysis of sucrose is called ______.

[10] Biomolecules
Chapter: [10] Biomolecules
Concept: undefined >> undefined

You are given four organic compounds “A”, “B” , “C” and “D”. The compounds “A”, “B” and “C” form an orange-red precipitate with 2, 4 DNP reagent. Compounds “A” and “B” reduce Tollen’s reagent while compounds “C” and “D” do not. Both “B” and “C” give a yellow precipitate when heated with iodine in the presence of NaOH. Compound “D” gives brisk effervescence with sodium bicarbonate solution. Identify “A”, “B”, “C” and “D” given the number of carbon atoms in three of these carbon compounds is three while one has two carbon atoms. Give an explanation for our answer.

[8] Aldehydes, Ketones and Carboxylic Acids
Chapter: [8] Aldehydes, Ketones and Carboxylic Acids
Concept: undefined >> undefined

When sucrose is hydrolysed the optical rotation values are measured using a polarimeter and are given in the following table:

S. No. Time (hours) Specific Rotation
1 0 + 66.5°
2 - 39.9°
  1. Account for the two specific rotation values.
  2. What is the specific name given to sucrose based on the above observation?
  3. One of the products formed during the hydrolysis of sucrose is a glucose, that reacts with hydroxylamine to give compound A. Identify compound A.
[10] Biomolecules
Chapter: [10] Biomolecules
Concept: undefined >> undefined

An organic compound A with the molecular formula (+) C4H9Br undergoes hydrolysis to form (+) C4H9OH. Give the structure of A and write the mechanism of the reaction.

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

 Acetic anhydride from acetic acid

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

Explain why Grignard reagents should be prepared under anhydrous conditions.

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

Which alkyl halide from the following pair would you expect to react more rapidly by an SN2 mechanism? Explain your answer.

\[\begin{array}{cc}\ce{CH3CH2CHCH3}\\
\phantom{.....}|\\
\phantom{......}\ce{Br}\\
\end{array}\] or \[\begin{array}{cc}\phantom{.......}\ce{CH3}\\
\phantom{...}|\\
\ce{H3C - C - Br}\\
\phantom{...}|\\
\phantom{.......}\ce{CH3}\\
\end{array}\]

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

Which alkyl halide from the following pair would you expect to react more rapidly by an SN2 mechanism? Explain your answer.

\[\begin{array}{cc}
\ce{CH3CHCH2CH2Br}\\
|\phantom{.............}\\
\ce{CH3}\phantom{..........}\\
\end{array}\] or \[\begin{array}{cc}
\ce{CH3CH2CHCH2Br}\\
|\\
\phantom{...}\ce{CH3}\\
\end{array}\]

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

Which one of the following is a food preservative? 

Equanil, Morphine, Sodium benzoate

 

[16] Chemistry in Everyday Life
Chapter: [16] Chemistry in Everyday Life
Concept: undefined >> undefined

Write the chemical equations involved in the following reactions:

Carbylamine reaction

[9] Amines
Chapter: [9] Amines
Concept: undefined >> undefined

How do you convert: 

2-bromobutane to but-2-ene

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined

Write the structural difference between starch and cellulose.

[10] Biomolecules
Chapter: [10] Biomolecules
Concept: undefined >> undefined

[NiCl4]2− is paramagnetic, while [Ni(CO)4] is diamagnetic, though both are tetrahedral. Why? (Atomic number of Ni = 28)

[5] Coordination Compounds
Chapter: [5] Coordination Compounds
Concept: undefined >> undefined

Write the main products when n-butyl chloride is treated with alcoholic KOH.

[6] Haloalkanes and Haloarenes
Chapter: [6] Haloalkanes and Haloarenes
Concept: undefined >> undefined
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