Birla Institute of Technology & Science, Pilani, Rajasthan - 333 031

IInd Semester 2015-2016

CHEM F342 ORGANIC CHEMISTRY IV Mid-Term Exam (Closed Book)
Max. Marks: 50 Duration: 90 minutes Date: 17th March 2016
Write your name and ID no. on the question paper. All questions are compulsory.
Q1. (i) Write the IUPAC or Hantzsch-Widman system names of the following compounds. [4x1=4]

(ii) Electrophilic substitution in thiophene takes place preferably at C-2 position as compared to C-3
position. Explain [3]

(iii) Arrange furan, benzene, thiophene, and pyrrole in the decreasing order of reactivity towards
electrophilic substitution and electrophilic addition reactions. [2x1=2]
Q2. (i) Identify the major product and propose a detailed mechanism for its formation, in each of the
following chemical transformations: [4+4+4+2=14]

Q3. (i) Identify the final products (A-H) in the following chemical transformations (No mechanism
required): [8x1=8]

(ii) Using appropriate reagents/solvents/reactants, convert succinic acid to diethyl furan-3,4-dicarboxylate

[4]
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Q4. (i) Draw the acyclic carbon chain framework of a sesquiterpenoid obtained by joining isoprene units.[1]

(ii) Citral, an acyclic monoterpenoid with molecular formula C10H16O, exists as two geometric isomers: (E)-
Citral and (Z)-Citral. When either of the isomers is first treated with Na in EtOH and then with dil. acid,
both form the corresponding cyclic alcohol: -terpineol (mol formula C10H18O). Write down the
corresponding two-step reactions. Explain, by showing the mechanism, which of the two isomers undergoes
faster cyclisation and why. [2+2]

(iii) Complete the following reaction sequence. What important structural information about camphor can be
inferred from these reactions? [2]

Q5. (a) Cholesterol is a monohydroxy steroid. In determining the position of the –OH group, cholesterol is
converted to Diel’s hydrocarbon. Show the reaction conditions and the products formed during the
conversion of cholesterol to Diel’s hydrocarbon in four steps consisting of reduction, oxidation, Grignard
reaction, and heating with Se. [3]

(b) Draw the chair conformer of a trans-trans-trans fused general steroid core. Show clearly the wedge-dash
bonds at the ring fusion. [2]

(c) The following reaction sequence represents the partial synthesis of estrone (a sex hormone) from
androstane. Complete the reaction sequence. [3]

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