ECH-X (UT-120) ECH-X (UT-120) ¶ß±Ó¬fl¡ ¬Û±Í¬Sê˜ ( B.D.P.) ø˙鬱¬ı¯∏«±ôL ¬Û¬ı˛œé¬± ( Term End Examination ) øÎ¬À¸•§¬ı˛, 2013 › Ê≈√Ú, 2014 [’±] ø¬ıøSê˚˛±-Œfl¡Ã˙˘¸˝√√ (i) ø¬ıøSê˚˛±&ø˘ÀÓ¬ Erythro-1-bromo-1,2diphenylpropane ‹ø26√fl¡ ¬Û±Í¬Sê˜ ( Elective ) √˙˜ ¬ÛS ( 10th Paper : Organic Chemistry-I ) ¸˜˚˛ – ≈√˝◊√ ‚KI◊±¬ ۔̫˜±Ú – 50 (ii) 9, 10 – phenanthraquinone 5 Full Marks : 50 [ ˜±ÀÚ¬ı˛ &èQ – 70% ] [‡] [’] Weightage of Marks : 70% 1,4-ά±˝◊√ ’…±ø˜ÀÚ±Ú…±¬ÛÔø˘Ú ŒÔÀfl¡ fl¡œˆ¬±À¬ı [’±] ø¬ıøSê˚˛±-Œfl¡Ã˙˘ ¸˝√√À˚±À· ÚœÀ‰¬¬ı˛ ø¬ıøSê˚˛±øÈ¬ÀÓ¬ ά◊»¬Ûiß ¬Û√±Ô« ˚¬Û√±Ô«&ø˘ ø˘‡≈Úº EtO2 CCH2 CH2 CH2 CH2 CO2 Et 10 × 2 = 20 Œ˚-Œfl¡±ÀÚ± ≈íøÈ¬ õ∂Àùü¬ı˛ ά◊M√¬ı˛ ø√Ú – 6 [fl¡] [’] ø¬ıøSê˚˛±-Œfl¡Ã˙˘¸˝√√ ÚœÀ‰¬¬ı˛ ø¬ıøSê˚˛±øÈ¬ÀÓ¬ Œ˚ Œ˚÷ ˚Œ˚÷&ø˘ ά◊»¬Ûiß ˝√√À¬ı Ó¬± ø˘‡≈Úº ¤¬ı— õ∂øÓ¬øÈ¬ fl¡±¬ı«Ú˚’ø'ÀÊ√Ú-¤¬ı˛ ¸—fl¡¬ı˛Ì ά◊À~‡ fl¡èÚ º ø¬ıøSê˚˛±øÈ¬¬ı˛ ø¶öøÓ¬˙øMê√ Œ˘‡ø‰¬S ’ÇÚ fl¡èÚ ¤¬ı— Œ˘‡ø‰¬SøÈ¬¬ı˛ Ó¬±»¬Û˚« ά◊À~‡ fl¡èÚº ¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… 4 ! NaOEt [ + [·] [’] øÚ•ßø˘ø‡Ó¬ Œ˚÷&ø˘¬ı˛ fl¡é¬fl¡ ø‰¬S ’ÇÚ fl¡èÚ CHCl2 " CF3 # # ##$ ........ B.Sc-5754-Y 5 ˙Ó¬±«¬ıø˘¸˝√√ ø¬ıøSê˚˛± Ò±¬Û&ø˘ ø˘‡≈Ú º ø¬ıˆ¬±· - fl¡ ! + ’…±ÚÔ˱ø¸√Ú ¸—Àù≠¯∏Ì fl¡¬ı˛À¬ıÚ ∑ ø¬ıøSê˚˛fl¡ ¤¬ı— ¬Ûø¬ı˛ø˜Ó¬ › ˚Ô±˚Ô Î¬◊M√ À¬ı˛¬ı˛ Ê√Ú… ø¬ıÀ˙¯∏ ˜”˘… Œ√›˚˛± ˝√√À¬ıº ’qX ¬ı±Ú±Ú, ’¬Ûø¬ı˛26√ißÓ¬± ¤¬ı— ’¬Ûø¬ı˛©®±¬ı˛ ˝√√ô¶±é¬À¬ı˛¬ı˛ Œé¬ÀS Ú•§¬ı˛ Œfl¡ÀȬ ŒÚ›˚˛± ˝√√À¬ıº ά◊¬Û±ÀôL õ∂Àùü¬ı˛ ˜”˘…˜±Ú ¸”ø‰¬Ó¬ ’±ÀÂ√º 1º ÚœÀ‰¬¬ı˛ ά◊»¬Ûiß Œ˚÷&ø˘ ø˘‡≈Ú – ¬ı˛¸±˚˛Ú ( Chemistry ) Time : 2 hours 2 ! B.Sc-5754-Y ! (i) CH2 = CH " CH = C = O (ii) CH2 = CH " CH = CH2 3 ECH-X (UT-120) [’±] øàø¬ı˛›ÀÊ√øÚfl¡ (stereogenic) Œfl¡f ¬ı˘ÀÓ¬ øfl¡ Œ¬ı±Á¡±˚˛ ∑ ¤fl¡±øÒfl¡ øàø¬ı˛›ÀÊ√øÚfl¡¡ Œfl¡f˚≈Mê√ Œ˚÷&ø˘ fl¡œ ¸¬ı«√±˝◊√ ’õ∂øÓ¬¸˜ ˝√√˚˛ ∑ ά◊¬Û˚≈Mê√ ά◊√±˝√√¬ı˛Ì¸˝√√ ¬ı…±‡…± fl¡èÚ º [˝◊√] ά◊√±˝√√¬ı˛Ì¸˝√√ Œ¬ı˛ÀÊ√±Ú…±k ˙øMê√¬ı˛ ¸—:± ø√Ú º ¸±˝◊√Àflv¡±À˝√√ø'Ú-Œfl¡ ˝√√±˝◊√ÀE±ÀÊ√ÀÚ˙Ú fl¡¬ı˛À˘ "1 120 kJ.mol Ó¬±¬Û˙øMê√ øÚ·«Ó¬ ˝√√˚˛ º Œ¬ıÚøÊ√ÚÀfl¡ ˝√√±˝◊√ÀE±ÀÊ√ÀÚ˙Ú fl¡¬ı˛À˘ "1 208 kJ.mol Ó¬±¬Û˙øMê√ øÚ·«Ó¬ ˝√√˚˛ º ! Œ¬ıÚøÊ√ÀÚ¬ı˛ Œ¬ı˛ÀÊ√±Ú…±k ˙øMê√ ·ÌÚ± fl¡èÚº 3 +2 +5 ! [‚] [’√] ø˜Ô±˝◊√˘ ¸±˝◊√Àflv¡±À˝√√À'ÀÚ¬ı˛ Œ‰¬˚˛±¬ı˛ ¬ı˛+¬Û&ø˘ øÚά◊˜…±Ú ’øˆ¬Àé¬¬Û ¸—Àfl¡ÀÓ¬ ’ÇÚ fl¡èÚ ¤¬ı— Ó¬±À√¬ı˛ ¶ö±ø˚˛ÀQ¬ı˛ Ó≈¬˘Ú± fl¡èÚº ˙øMê√ Œ˘‡ø‰¬ÀS¬ı˛ ¸±˝√√±À˚… Œ‰¬˚˛±¬ı˛ › ŒÚÃfl¡± ’±fl‘¡øÓ¬ ¤¬ı— Œ‰¬˚˛±¬ı˛ › Œ˜±‰¬Î¬ˇ±ÀÚ± ŒÚÃfl¡± ¬ı˛+À¬Û¬ı˛ ˜ÀÒ… ˙øMê√ ¬Û±Ô«fl¡… Œ√‡±Ú º ECH-X (UT-120) 4 ø¬ıˆ¬±· - ‡¡ 2º 6 × 3 = 18 Œ˚-Œfl¡±ÀÚ± øÓ¬ÚøÈ¬ õ∂Àùü¬ı˛ ά◊M√¬ı˛ ø√Ú – [fl¡] ∆Ê√¬ı Œ˚÷ ¸—Àù≠¯∏ÀÌ øÚ•ßø˘ø‡Ó¬ ø¬ıfl¡±¬ı˛fl¡&ø˘¬ı˛ 2×3 ¬ı…¬ı˝√√±¬ı˛ ά◊À~‡ fl¡èÚ – [’] ¢∂œ·Ú±Î«¬ ø¬ıfl¡±¬ı˛fl¡ [’±] ›¸ø˜˚˛±˜ ŒÈ¬À¬∏C±'±˝◊√ά [˝◊√] Œˆ¬Ê√± ˝◊√Ô±À¬ı˛ Œ¸±øÎ¬˚˛±˜ Ò±Ó≈¬ [‡] [’] CH3CHOHCH = CH Br-¤¬ı˛ ¸¬ıfl¡˚˛øÈ¬ ¸y±¬ı… øS˜±øSfl¡ ¸˜±¬ı˚˛¬ı ’ÇÚ fl¡èÚ ¤¬ı— ¸˜±¬ı˚˛¬ı&ø˘¬ı˛ ø¬ıÚ…±¸ ! R/S ¤¬ı— E/Z øÚÀ«√˙ fl¡èÚº [’±] (+)-2-’±À˚˛±Àά±’À"√√Ú-¤¬ı˛ ¸±ÀÔ ¬ÛȬ±ø¸˚˛±˜ ’±À˚˛±Î¬±˝◊√ά-¤¬ı˛ ’…±ø¸ÀȬ±Ú ^±¬ıÀfl¡ õ∂dÓ¬ [’±] øSê˚˛±-Œfl¡Ã˙˘¸˝√√ øÚ•ßø˘ø‡Ó¬ ø¬ıøSê˚˛±øÈ¬ÀÓ¬ ά◊»¬Ûiß ¬Û√±Ô«-¤¬ı˛ Ú±˜ ά◊À~‡ fl¡èÚº ^¬ıÌøÈ¬ ø˜ø|Ó¬ fl¡À¬ı˛ ø¬ıøSê˚˛± fl¡¬ı˛±ÀÚ± ˝√√˘º ^¬ıÌøÈ¬¬ı˛ ’±À˘±fl¡¸øSê˚˛Ó¬± Sê˜˙ fl¡˜ÀÓ¬ Ô±Àfl¡ ¤¬ı— ’¬ıÀ˙À¯∏ ˙”Ú… ˝√√˚˛º — ¬Û˚«À¬ıé¬ÌøÈ¬ ¬ı…±‡…± 6 B.Sc-5754-Y + fl¡èÚº 4 [¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… B.Sc-5754-Y 4+2 ECH-X (UT-120) [·] øÚ•ßø˘ø‡Ó¬ ¬Ûø¬ı˛¬ıÓ«¬Ú&ø˘ øfl¡ˆ¬±À¬ı ¸•Ûiß fl¡¬ı˛À¬ıÚ ∑ 2×3 ECH-X (UT-120) [‰¬] [’] ¸˜ 2 ’±Ìø¬ıfl¡ ’Ú≈¬Û±ÀÓ¬¬ı˛ Ȭ˘≈˝◊√Ú, Ú±˝◊√À¬∏C±À¬ıÚøÊ√ÀÚ¬ı˛ ø˜|ÌÀfl¡ ¸˜ ’±Ìø¬ıfl¡ [’] Œ¬ıÚøÊ√Ú " "# ’Ú≈¬Û±ÀÓ¬¬ı˛ ’…±ø¸È¬±˝◊√˘ Œflv¡±¬ı˛±˝◊√ά › ’øÓ¬ø¬ı˛Mê√ ¬Ûø¬ı˛˜±Ì ’Ú±^« ’…±˘≈ø˜øÚ˚˛±˜ Œflv¡±¬ı˛±˝◊√ά-¤¬ı˛ [’±]! ¬1,3-ø¬ıά◊Ȭ±Î¬±˝◊√Ú " "# ø˜|À̬ı˛ ¸±ÀÔ ø¬ıøSê˚˛± fl¡¬ı˛±ÀÚ± ˝√√˘º ø¬ıøSê˚˛± [˝◊√] ¬’…±ø¸øÈ¬ø˘Ú " "# ø¸¸ƒ-2-ø¬ıά◊øÈ¬Úº ! [‚] fl¡±¬ı˛Ì¸˝√√ øÚÀ‰¬¬ı˛ øÚÀ«√˙ ’Ú≈˚±˚˛œ ¸±Ê√±Ú – 2×3 [’] I"!, F " , Cl" , Br" [Ê√˘œ˚˛ ¬^¬ıÀÌ øÚά◊øflv¡À˚˛±øÙ¬ø˘ø¸øÈ¬¬ı˛ S꘬ıÒ«˜±Ú ˜±Ú ’Ú≈˚±˚˛œ ] ! [’±] HO, C H O, CH " COO, (CH ) CO 2 5 3 33 [鬱¬ı˛œ˚˛ ÒÀ˜«¬ı˛ S꘬ıÒ«˜±Ú ˜±Ú ’Ú≈˚±˚˛œ ] [˝◊√] ø¬ıøSê˚˛±Ê√±Ó¬ Œ˚÷&ø˘ ø˘‡≈Ú – Œ˙À¯∏ ά◊Mê√ ø˜|ÀÌ Œfl¡±Úƒ Œfl¡±Úƒ Œ˚÷ øfl¡ ’Ú≈¬Û±ÀÓ¬ Ô±fl¡À¬ı Ó¬± ø˘‡≈Úº ø¬ıøSê˚˛±-Œfl¡Ã˙˘¸˝√√ ¬ı…±‡…± fl¡èÚº [’±] øÚ•ßø˘ø‡Ó¬ ¬ı˛+¬Û±ôL¬ı˛øÈ¬ øfl¡¬ı˛+À¬Û ¸•Û±√Ú fl¡¬ı˛À¬ıÚ ∑ ! [˝◊√] øÚ•ßø˘ø‡Ó¬ fl¡±À¬ı«±fl¡…±È¬±˚˛ÚøÈ¬¬ı˛ fl¡…±ÀÚ±øÚfl¡…±˘ ·Í¬Ú&ø˘ ’ÇÚ fl¡èÚ ¤¬ı— ¤À√¬ı˛ ˜ÀÒ… Œfl¡±ÚƒøÈ¬¬ı˛ ’±À¬Ûøé¬fl¡ ’¬ı√±Ú ¸¬ı ŒÔÀfl¡ Œ¬ı˙œ [„√√] øÚø«√©Ü ά◊√±˝√√¬ı˛Ì¸˝√√ øÚ•ßø˘ø‡Ó¬ ø¬ı¯∏˚˛&ø˘ ¸•§Àg Ȭœfl¡± ø˘‡≈Ú – [’] ¤©Ü±À¬ı˛¬ı˛ ’±^«ø¬ıÀù≠¯∏À̬ı˛ Œé¬ÀS A AL1 ø¬ıøSê˚˛± Œfl¡Ã˙˘ [’±] ¬¬ı·±È«¬-fl≈¡fl¡ ¬ÛXøÓ¬ ¡Z±¬ı˛± øÙ¬Ú±ÚøÔËÚ ¸—Àù≠¯∏Ì º ! 3+3 B.Sc-5754-Y [ ¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… fl¡±¬ı˛Ì¸˝√√ ø˘‡≈Úº 3+1+2 B.Sc-5754-Y 3 3º ECH-X (UT-120) ø¬ıˆ¬±· - ·¡ Œ˚-Œfl¡±ÀÚ± ‰¬±¬ı˛øÈ¬¬ õ∂Àùü¬ı˛ ά◊M√¬ı˛ ø√Ú – 3 × 4 = 12 [fl¡] ¬∏C±k-1,3-ά±˝◊√ø˜Ô±˝◊√˘ ¸±˝◊√Àflv¡±À˝√√À'Ú ’±À˘±fl¡ øÚø¶ç¡˚˛ — ø¬ı¯∏˚˛øÈ¬ ¬ı…±‡…± fl¡èÚº 3 [‡] øÚ•ßø˘ø‡Ó¬ Œ˚÷&ø˘¬ı˛ ¬ IUPAC ÛXøÓ¬ÀÓ¬ Ú±˜fl¡¬ı˛Ì fl¡èÚ – 3 [’] Cl " CH2 CHI CH (CH3).CH2 CH2 Br [’±] ! [˝◊√] ECH-X (UT-120) 4 [„√√] øÚ•ßø˘ø‡Ó¬ Œ˚÷&ø˘¬ı˛ Œ¬ı˛ø¸ø˜fl¡ ø˜|ÌÀfl¡ fl¡œ ¬Û‘Ôfl¡œfl¡¬ı˛Ì fl¡¬ı˛± ˚±À¬ı ∑ 11 ×2 2 [‰¬] [’¬] øÚ•ßø˘ø‡Ó¬ ŒÊ√±Àάˇ¬ı˛ Œ˚÷&ø˘¬ı˛ øÚÀ«√ø˙Ó¬ [*] fl¡±¬ı«ÀÚ¬ı˛ Œfl¡±ÚƒøÈ¬ÀÓ¬ ˝◊√À˘fl¡¬∏C!Ú ‚ÚQ Œ¬ıø˙ ∑ ¬ı…±‡…± fl¡èÚ º [·] øÚ•ßø˘ø‡Ó¬ Œ˚÷&ø˘¬ı˛ fl¡±˝◊√¬ı˛±˘ fl¡±¬ı«Ú ¬Û¬ı˛˜±Ì≈&ø˘Àfl¡ R–/S – ¡Z±¬ı˛± ø‰¬ø˝êÓ¬ fl¡èÚ – 3 [‚] [ƒ’] ≈√øÈ¬ ¬Û‘Ôfl¡ ’…±˘øfl¡Ú Œ˚÷Àfl¡ ¬Û‘Ôfl¡ˆ¬±À¬ı S꘬Û˚±«À˚˛ ά±˝◊√À¬ı±À¬ı˛Ú › 鬱¬ı˛œ˚˛ ˝√√±˝◊√ÀE±ÀÊ√Ú ¬Û±¬ı˛’'±˝◊√ά ^¬ıÀ̬ı˛ ¸±ÀÔ ø¬ıøSê˚˛± ‚Ȭ±ÀÚ± ˝√√À˘ 2-ø¬ıά◊Ȭ±Ú˘ ά◊»¬Ûiß ˝√√˚˛º ’…±˘øfl¡Ú Œ˚÷&ø˘Àfl¡ ˙Ú±Mê√ fl¡èÚº ø¬ıøSê˚˛±&ø˘ ά◊À~‡ fl¡èÚº [’±] øÚÀ•ß ¬ıøÌ«Ó¬ ø¬ıøSê˚˛±˚˛ ά◊»¬Ûiß Œ˚÷øÈ¬ ø˘‡≈Ú º [’±¬] øÚ•ßø˘ø‡Ó¬ Œ˚÷&ø˘Àfl¡ ¬ı˛±¸±˚˛øÚfl¡ ¬Û¬ı˛œé¬±¬ı˛ ˜±Ò…À˜ ¬Û±Ô«fl¡… fl¡èÚ – Œflv¡±À¬ı˛±À¬ıÚøÊ√Ú, ¸±˝◊√Àflv¡±À˝√√'±˝◊√˘ Œflv¡±¬ı˛±˝◊√άº 2+1 11 ×2 [Â√] øfl¡¬ı˛+À¬Û ¬ı˛+¬Û±ôL¬ı˛&ø˘ ‚Ȭ±À¬ıÚ ∑ 2 ˝◊√Ô±˝◊√˘ ø˜Ô±˝◊√˘ øfl¡ÀȬ±Ú ! 2+1 B.Sc-5754-Y [¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… B.Sc-5754-Y ECH-X (UT-120) ECH-X (UT-120) ( English Version ) (b) Special credit will be given for precise and correct answer. Marks will be deducted for spelling mistakes, untidiness and illegible handwriting. The figures in the margin indicate full marks. EtO2 CCH2 CH2 CH2 CH2 CO2 Et 6+4 C) 1. Answer any two questions : A) (a) (a) 10 × 2 = 20 CHCl2 " CF3 # # ##$ ......... Draw the potential energy diagram for ! point out the characteristics of the curve. (b) Identify the product(s) with mechanism : (i) (a) (i) CH2 = CH " CH = C = O (ii) CH2 = CH " CH = CH2 always 9, 10 – phenanthraquinone asymmetric (c) ? Explain with Define Resonance energy with example. Heat of hydrogenation of cyclohexene is 120 kJ.mol "1 "1 and that of benzene is 1,4-diaminonaphthalene ? Show the 208 kJ.mol steps with reagents and conditions. ! of benzene. energy [ of suitable examples. How will you prepare anthracene from B.Sc-5754-Y state ! Are the compounds with such centres Erythro-1-bromo-1,2- 5+5 B) the ! (b) What is meant by stereogenic centre ? diphenylpropane (ii) indicating hybridisation of each carbon/oxygen. NaOEt and Draw the orbital picture of the following compounds Predict the product(s) with mechanism. reaction Identify the product(s) with mechanism: ! Group-A the 2 ¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… B.Sc-5754-Y ! . Calculate the resonance 3+2+5 3 D) (a) ECH-X (UT-120) Draw the chair conformations of methyl cyclohexane in Newman ECH-X (UT-120) B) (a) possible stereoisomers and of designate them as R/S/E/Z. formula and compare their stabilities. ! (b) (+)-2-Iodooctane is treated with KI in the energy differences between chair acetone solvent. The optical activity of and the solution boat, chair and twist boat will decline to zero. Explain the observation. conformations. (b) all CH3CHOHCH = CH Br projection With the help of energy diagram show Draw 4 Predict the product with mechanism : C) 4+2 How would you carry out the following transformations : 2×3 (a) 6+4 Group -B 2. Answer any three questions : A) Write the uses of the following reagents in (b) 6 × 3 = 18 (c) . the synthesis of organic compounds : 2×3 (i) (ii) D) indicated below : Grignard reagent (a) Osmium tetroxide I" , F " , Cl" , Br" order (iii) Sodium metal in moist ether. ! B.Sc-5754-Y Arrange the following, with reasons, as [¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… of solution ) B.Sc-5754-Y ( in the nucleophilicity increasing in aqueous ECH-X (UT-120) (b) ECH-X (UT-120) HO, C 2 H5 O, CH3 " COO, (CH3)3 CO ( in 2 (b) Carry out the following transformation : (c) Write the increasing order of basic character) ! (c) Identify the products. the canonical forms of the following carbocation and indicate with reason, the most contributing canonical form : 2×3 E) Write notes on the following with example : (a) 3+1+2 A AL1 mechanism in case of hydrolysis Group-C of ester. ! (b) Synthesis of Phenanthrene by BogertCook method. F) (a) 3+3 3. Answer any four questions : (A) (B) of acetyl presence of aluminium chloride chloride excess ? with (b) ! (c) mechanism involved. B.Sc-5754-Y [ ¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… 3 Give the IUPAC names of the following (a) in anhydrous Explain is compounds : nitrobenzene is treated with equimolar proportion cyclohexane optically inactive. — Explain. What would be the product composition if an equimolar mixture of toluene and Trans-1,3-dimethyl 3 × 4 = 12 B.Sc-5754-Y Cl " CH2 CHI CH (CH3).CH2 CH2 Br 3 3 (C) ECH-X (UT-120) Assign R–/S – descriptors for the chiral centres in the following compounds : ECH-X (UT-120) (F) 4 (a) Which compound of the following 3 pair will have higher electron density at the marked ( * ) carbon atom ? Explain. (D) (a) Two different alkenes produce 2-butanol when treated separately with diborane followed by treatment with alkaline hydrogen peroxide solution. Identify (b) Distinguish between the following the alkenes. Write down the reactions compounds with the help of involved. (b) chemical reaction : Identify the product : Chlorobenzene, Cyclohexylchloride Ethyl methyl ketone 2+1 2+1 (E) Explain whether the following recemic (G) How would you convert ? 1 compounds would be resolvable : ! 11 × 2 2 B.Sc-5754-Y [¬ÛÀ¬ı˛¬ı˛ ¬Û‘ᬱ˚˛ ^©Ü¬ı… ! B.Sc-5754-Y 1 2 ×2
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