Question of 90
Q.(a) Write the IUPAC names of the products obtained by the addition reaction of HBr to hex-1-ene:
(i) in the absence of peroxide
(ii) in the presence of peroxide. [2]
(b) Draw the Cis and trans structures of hex-2-ene. Which isomer will have the higher boiling point and why? [2]
(c) Give the chemical reaction to convert Ethyne into benzene. [1]
OR
(a) How will you convert Propyne into propane? (Give only the chemical equation.) [2]
(b) Sodium salt of which acid will be needed for the preparation of propane? Write the chemical equation for the reaction. [2]
(c) Write the structure of 2-Ethyl pentane. Why is the given name incorrect? Write the correct IUPAC name. [1]
Rajasthan RbseRajasthan Board Senior Secondary Part-I Examination 2017Subjective· 5mImportance★★★★★
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Start your 14-day free trial to unlock the full solution →(a) HBr adds Markovnikov-fashion (2-bromohexane) without peroxide, and anti-Markovnikov (1-bromohexane) with peroxide. (b) cis-Hex-2-ene boils higher than trans-hex-2-ene because it is polar. (c) Three molecules of ethyne cyclotrimerise over a red-hot iron tube to give benzene.
(a) HBr addition to hex-1-ene, CH2=CH-CH2-CH2-CH2-CH3:
- In the absence of peroxide, addition follows Markovnikov's rule: the H atom adds to the carbon of the double bond that already has more hydrogens (C1), and Br adds to the more substituted carbon (C2), because the reaction proceeds via the more stable secondary carbocation intermediate. Product: 2-bromohexane, CH3-CHBr-CH2-CH2-CH2-CH3.
- In the presence of peroxide, the reaction proceeds by a free-radical chain mechanism (the peroxide/Kharasch effect), reversing the usual regiochemistry: Br adds first to the terminal, less hindered carbon (C1) to give the more stable secondary radical at C2, so Br ends up on the terminal carbon. Product: 1-bromohexane, Br-CH2-CH2-CH2-CH2-CH2-CH3.
(b) cis- and trans-hex-2-ene, CH3-CH=CH-CH2-CH2-CH3:
cis-Hex-2-ene: the CH3 group (on C2) and the propyl (CH2CH2CH3) group (on C3) lie on the SAME side of the double bond.
trans-Hex-2-ene: the CH3 group and the propyl group lie on OPPOSITE sides of the double bond. …
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