Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide, the same reaction yields 1-bromopropane. Explain and give mechanism.
Addition of HBr to propene is an example of an electrophilic substitution reaction.
Hydrogen bromide provides an electrophile H+. This electrophile attacks the double bond to form 1° and 2° carbocations.
Secondary carbocations are more stable. Hence, the former predominates since it will form at faster rate. Thus, in the next step, Br- attacks the carbocation to form 2 - bromopropane as major product.
This reaction follows Markovnikov's rule where the negative part of the addendum is attached to the carbon atom having a lesser number of hydrogen atoms.
In the presence of benzoyl peroxide, an addition reaction takes place anti to Markovnikov's rule. The reaction follows a free radical chain mechanism as:
Secondary free radicals are more stable than primary radicals. Hence, the former predominates since it forms at a faster rate. Thus, 1 - bromopropane is obtained as the major product.
In the presence of peroxide, Br free radical acts as an electrophile. Hence, two different products are obtained on addition of HBr to propene in the absence and presence of peroxide.
An alkene 'A' on ozonolysis gives a mixture of ethanal and pentan-3-one. Write structure and IUPAC name of 'A'.
Write IUPAC names of the products obtained by the ozonolysis of the following compounds:
(i) Pent-2-ene
(ii) 3,4-Dimethyl-hept-3-ene
(iii) 2-Ethylbut-1-ene
(iv) 1-Phenylbut-1-ene
How would you convert the following compounds into benzene?
(i) Ethyne (ii) Ethene (iii) Hexane
Why does benzene undergo electrophilic substitution reactions easily and nucleophilic substitutions with difficulty?
Arrange benzene, n-hexane and ethyne in decreasing order of acidic behaviour. Also give reason for this behaviour.
Explain why the following systems are not aromatic?
Why is Wurtz reaction not preferred for the preparation of alkanes containing odd number of carbon atoms? Illustrate your answer by taking one example.
Arrange the following set of compounds in order of their decreasing relative reactivity with an electrophile, E+
(a) Chlorobenzene, 2,4-dinitrochlorobenzene, p-nitrochlorobenzene
(b) Toluene, p-H3C-C6H4-NO2, p-O2N-C6H4-NO2.
How do you account for the formation of ethane during chlorination of methane?
What are the necessary conditions for any system to be aromatic?
What are hybridisation states of each carbon atom in the following compounds ?
(i) CH2=C=O,
(ii) CH3CH=CH2,
(iii) (CH3)2CO,
(iv) CH2=CHCN,
(v) C6H6
What will be the minimum pressure required to compress 500 dm3 of air at 1 bar to 200 dm3 at 30°C?
What are the common physical and chemical features of alkali metals?
Calculate the molecular mass of the following:
(i) H2O
(ii) CO2
(iii) CH4
Assign oxidation number to the underlined elements in each of the following species:
(a) NaH2PO4
(b) NaHSO4
(c) H4P2O7
(d) K2MnO4
(e) CaO2
(f) NaBH4
(g) H2S2O7
(h) KAl(SO4)2.12 H2O
What is the basic theme of organisation in the periodic table?
Explain the formation of a chemical bond.
Choose the correct answer. A thermodynamic state function is a quantity
(i) used to determine heat changes
(ii) whose value is independent of path
(iii) used to determine pressure volume work
(iv) whose value depends on temperature only.
A liquid is in equilibrium with its vapour in a sealed container at a fixed temperature. The volume of the container is suddenly increased.
a) What is the initial effect of the change on vapour pressure?
b) How do rates of evaporation and condensation change initially?
c) What happens when equilibrium is restored finally and what will be the final vapour pressure?
Justify the position of hydrogen in the periodic table on the basis of its electronic configuration.
Calculate the enthalpy change on freezing of 1.0 mol of water at 10.0°C to ice at -10.0°C. ΔfusH = 6.03 kJ mol-1 at 0°C.
Cp[H2O(l)] = 75.3 J mol-1 K-1
Cp[H2O(s)] = 36.8 J mol-1 K-1
Calculate the pH of the following solutions:
(a) 2 g of TlOH dissolved in water to give 2 litre of solution.
(b) 0.3 g of Ca(OH)2 dissolved in water to give 500 mL of solution.
(c) 0.3 g of NaOH dissolved in water to give 200 mL of solution.
(d) 1mL of 13.6 M HCl is diluted with water to give 1 litre of solution.
The value of Kc for the reaction
3O2 (g) ↔ 2O3 (g) is 2.0 ×10–50 at 25°C.
If the equilibrium concentration of O2 in air at 25°C is 1.6 ×10–2, what is the concentration of O3?
What characteristics do you expect from an electron-deficient hydride with respect to its structure and chemical reactions?
Is there any change in the hybridisation of B and N atoms as a result of the following reaction?
BF3 + NH3 → F3B.NH3
Define electronegativity. How does it differ from electron gain enthalpy?
What is the SI unit of mass? How is it defined?
Why is Li2CO3 decomposed at a lower temperature whereas Na2CO3 at higher temperature?
In Ostwald's process for the manufacture of nitric acid, the first step involves the oxidation of ammonia gas by oxygen gas to give nitric oxide gas and steam. What is the maximum weight of nitric oxide that can be obtained starting only with 10.00 g. of ammonia and 20.00 g of oxygen?
Justify that the following reactions are redox reactions:
(a) CuO(s) + H2(g) → Cu(s) + H2O(g)
(b) Fe2O3(s) + 3CO(g) → 2Fe(s) + 3CO2(g)
(c) 4BCl3(g) + 3LiAlH4(s) → 2B2H6(g) + 3LiCl(s) + 3 AlCl3 (s)
(d) 2K(s) + F2(g) → 2K+F– (s)
(e) 4 NH3(g) + 5 O2(g) → 4NO(g) + 6H2O(g)
Why the HCl,HF and HI don't show peroxide effect
Why the HCl,HF and HI don't show peroxide effect