Organic Photochemistry and Pericyclic Reactions
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1 rganic otochemistry and Pericyclic Reactions nswers. Find out the major product & provide mechanism? a) Mechanism: * - cleavage - C b) Mechanism: * - cleavage - C c) Mechanism: * - cleavage - abstraction
2 d) Mechanism: * - cleavage. Give mechanism for the given transformation. a) * - abstraction - cleavage abstraction b) * - abstraction from solvent c) * - C C C d) * - abstraction. Complete the following reaction & give their mechanism?
3 a) h int: Mechanism involves Peterno Buchi reaction followed by oxetane ring opening + h unstable b) Et C C Et h CEt CEt Mechanism: Et C C Et [ + ] cycloaddition h CEt CEt c) h Mechanism: h [ + ] cycloaddition
4 d) h 4. Write the possible mechanism for the following photochemical transformation. a) * C C or C C C b) *
5 c) * d) C 6 5 C 6 5 * C 6 5 C 6 5 C 6 5 C 6 5 C 6 5 C transfer 5. Write the major product. int: These examples follow oto intramolecular cycloaddition a) ensitizer b) ensitizer
6 c) ensitizer 6. Write the major product & provide mechanism int: lkyl ryl thiones having δ C bond undergo intramolecular abstraction a) 0 int: romatic thiones with vacant peri position undergo reductive cyclization b) * 7. Find out the products in the following transformation.
7 a) Me C 4e - conrotatory C Me electrocyclic C Me Et C C Et C Me Me C s 4 + s C Et C M e C Et Et C C Et B 4e - conrotatory c) electrocyclic b) Et C C Et disrotatory Et C C Et disrotatory C Et C Et C Et C photochemical 8e - electrocyclic C Et C Et thermal 6e - electrocyclic C Et D 4e - conrotatory c) electrocyclic Et C C Et Et C C Et C Et C Et 8) uggest mechanism for the following transformation. int: Rosebengal generates singlet oxygen a) b)
8 c) 9. Predict the major product. - Et Me Et c. C C d. CMe CMe cyclohexane 0. Complete the given reaction and give the mechanism. int: Di-π methane rearrangment
9 5 h bond formation 4 between C and C4 bond breaking between C and C4 bond fromation between C4 and C5 Fromation of bond between C and C 4 5 T ens 4 5 bond formation between C and C4 bond breaking between C and C bond fromation between C and C5 c. 5 4 T ens 5 4 bond formation between C and C4 bond breaking between C and C bond fromation between C and C5 d. int: xa Di-π Methane rearrangement
10 d.. Write all the four products obtained in the given reaction. Find out the product and B in the given transformation and explain the difference in the photoreaction (C ) C (C ) C B int: In the case of cis transformation i.e. a γ- abstraction is possible where as in trans it is not possible (not spatially close)
11 * - abstraction * * C C. Find out the product missing in the given transformation
12 , - shift bond breaking nm B, bonding C nm D cycloaddition E 4. Predict the major product for the given transformation - int: extrusion occurs upon irradiation of pyrazolines
13 c. - C int: oto Wolff rearrangement: inglet carbene formed by loss of is stabilised by rearrangement to ketene. 5. Predict the product of the following transformations c Me Me c Me c Me Me Me C CC C CC C, shift of Me group CC C CC C CC
14 c. c c 6. Find the intermediates formed during the following transformation B C - 7. Predict the stereochemistry of the following pericyclic reaction ` e - (4n ) disrotatory electrocyclic retention cis 6 e - (4n + ) conrotatory electrocyclic c. R 6 e - (4n + ) conrotatory electrocyclic R 8. Predict the structure of and B in the given transformation.
15 hv cis-trans hv B 9. Predict the product 80 o C int: Cope rearrangement K, dioxane nionic oxy - cope rearrangement + c. d.
16 0. Predict the product. C c. C. Write the product and give their mechanism. [, 7] ntarafacial D [, 7] ntarafacial D C c. 4 [, 5] 5 C d. hv [, 7] shift otochemical suprafacial
17 . Write the major product int: Diels lder reaction Me Me Me Me c. Me Me. Find out the and B in the following transformation. C C electrocyclic ring opening Intramolecular Diels lder C
18 4. Find out and B in the following transformation. B 5. Find out the and B in the following transformation. chelotropic elimination B 6. Find out the intermediates. int: Benzyne is produced by diazotisation of anthranalic acid
19 R B 7. Find out the product. CEt CEt c. - Et Me Et
20 d. MeC CMe CMe CMe 8. Find out the product. C - itrile xide Intramolecular, dipolar addition, - Dipolr species having dipolariphilic part, dipolar addition - B Zn/c C
21 C / - c. C C 6 5 C6 5 C C C 9. Predict the product. B C 6 5 C 6 5 C C C CMe, dipolar addition CMe + c. C C mole ozone C C C C C 0. Predict the major photoproduct. / hv,rose bengal C C C C C C + 00 o C CMe MeC
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