In 1825, Michael Faraday isolated a compound, benzene, from the oil which collected in the gas pipes in London and determined that it had an empirical formula of CH. what are the magnetic properties of solids?? Assume That Benzene Is A Two-dimensional Box. The COH bond has 2 bonded pairs and 2 lone pairs (on the oxygen atom), so the bond angle is 104.5 (V-shaped or bent). In this ScienceStruck post, we provide you with the polarity and steps to create the Lewis dot diagram of this aromatic compound. We can represent the electrons in a carbon atom that are available to make bonds in an orbital diagram as shown below: Each arrow (↑ or ↓) represents an electron (spin up or spin down, spin quantum number +½ or -½). Please enable javascript and pop-ups to view all page content. (d) … These electron pairs are known as shared pairs or bonding pairs, and the stable balance of attractive and repulsive forces between atoms, when they share electrons, is known as covalent bonding. So, the possible structures for benzene involving double and/or triple bonds arranged in a chain seemed most unlikely as these should undergo addition reactions. In 1940 it was suggested that benzene is NOT made up of the two structures above in rapid equilibrium, but that each benzene molecule is resonating between the structures as shown below: This means that the electrons making up the bonds in each single molecule of benzene are actually constantly in motion, producing the resonance hybrid structure which is the composite, or average, structure so that each carbon-carbon bond is identical and halfway between the length of a single and a double bound. SF3 is a radical, and the bond angle has not been determined. The bond angle in alcohols is slightly less than the tetrahedral angle (109°-28′). The Kekulé structure for benzene meant that there were two distinct structures of C6H6 in rapid equilibrium with each other. Due to the delocalised electron ring each bond angle is equal, therefore is a hexagon with internal bond angles of 120 degrees each. The first energy level is full (1s2) so the 1s electrons are not available for bonding. All the carbon-carbon bond angles in benzene are identical, 120°. Before we talk about the hybridization of C6H6 let us first understand the structure of benzene. Question: Benzene Is A Cyclic Aromatic Hydrocarbon (C6H6). There is a formation of a sigma bond and a pi bond between two carbon atoms. One lobe of the 2p orbital lies above the plane of the benzene molecule and one lobe lies below the plane of the benzene molecule as shown below: This enables the sides of the lobes of each 2p orbital to overlap the sides of the lobes of the adjacent 2p orbitals. If benzene was a straight-chain unsaturated hydrocarbon it should readily undergo addition reactions (just like other alkenes and alkynes). 43.4. C2H4 Molecular Geometry And Bond Angles. So, in 1872 Kekulé proposed a benzene structure composed of three alternate single and double bonds as shown below: Please note that although the carbon atoms are not written within the structure, it is always understood that a cabon atom exists where two lines of the hexagon join, so that there are 6 "joins", 6 angles, and therefore 6 carbon atoms. Because the oxygen-centred lone pairs are close to the oxygen (and not bound to a neighbouring atom), these tend to compress the /_C-O-C bond angle to give a value of 105^@ rather than 109. It even goes a long way towards explaining why benzene does not readily undergo addition reactions, because it does not contain double bonds like the unsaturated hydrocarbons (alkenes and alkynes). What is the standard enthalpy of combustion of glucose, C6H12O6? C2H4 molecular geometry is said to be planar in structure while the sp 2 orbitals are placed at a bond angle of 120 o. It is formed into a planar ring with equal bond lengths between all of the carbon atoms. Bf3-3. In order to resolve this problem, Kekulé proposed that the benzene ring is in rapid equilibrium between structures in which the double bonds are in the alternative positions as shown below: So, when bromine reacts with C6H5Br in a substitution reaction to produce C6H4Br2, pairs of structural isomers of C6H4Br2 are in equilibrium with each other. which of the following complete lewis diagrams represents a molecule with a bond angle that is closest to 120º? The has a linear structure. X. start new discussion. As a result, the bonding pairs move away from the lone 2 c 2014 Advanced Instructional Systems, Inc. and NC State College of … The three sp2 hybrid molecular orbitals around each carbon nucleus in the benzene molecule will lie as far apart from one another as possible, that is, the three sp2 hybrid molecular orbitals lie in a plane with angles of 120° between them. Carbon does not use these 4 atomic orbitals in their pure states for bonding, instead, carbon hybridizes (blends) its second energy atomic orbitals to form hybrid molecular orbitals. We find that all the carbon-carbon bond lengths in benzene are all the same, they are all 1.4 Å, which is half-way between the length of a C-C bond and the length of a C=C bond. As is clear, the framework of carbon and hydrogen atoms is coplanar with H-C-C or C-C-C bond angle as 120°. All the carbon-carbon bond lengths in benzene are identical, 1.4 Å (1.4 × 10-10 m) In structural formulae, benzene (C 6 H 6) is usually drawn as a hexagon with a circle inside it: Compounds containing a benzene ring … The bond angle is the angle formed by the intersection of two bonds. There is one electron in each of the three sp2 hybrid molecular orbitals, and one electron in the unhybridized 2p orbital. If bromine is added to benzene in the presence of FeBr3, it undergoes a substitution reaction in which one of the hydrogen atoms is replaced by a bromine atom to produce a compound with the formula C6H5Br, as shown below: In this respect, benzene was behaving much more like a saturated hydrocarbon (only single bonds between carbon atoms). ishu259491 ishu259491 Answer: Bg3 this is the answer given in my book. Benzene is the simplest aromatic hydrocarbon. Experimental studies, especially those employing X-ray diffraction, show benzene to have a planar structure with each carbon-carbon bond distance equal to 1.40 angstroms (Å). This means that structural isomers 1 and 4 shown above, which only differ in that Br atoms are bonded across a single bond or a double bond, are now in rapid equilibrium with each other as shown below: According to Kekulé, these two structural isomers of C6H4Br2 are in such rapid equilibrium that they cannot be separated out as two separate molecules, so it appears that there are only 3 isomers instead of 4. Benzene is a planar 6 membered cyclic ring, with each atom in the ring being a carbon atom (Homo-aromatic). W… The standard enthalpy of formation of glucose is -1273.3kJ/mol, and for carbon dioxide it is -393.5kJ/mol, and for water -285.8 kJ/mol. Carbon-hydrogen bond length is 109 pm (1.09 Angstroms) Benzene is a delocalised pi-system formed via the overlap of carbon's py orbitals forming a ring of electron density above and below the plane of the benzene ring. 2. Benzene does not readily undergo addition reactions. IV: Butane - has all single bonds making the longest bond lengths. Hence, the bond angles is 109.5 o. DMG. Benzene is an organic compound with the molecular formula C6H6. The bond angle of is 180 Explanation: In order to find the bond angle, the molecular geometry of must be first observed. Benzene is a planar regular hexagon, with bond angles of 120°. $\endgroup$ – J. LS Jan 8 '15 at 17:20 1. reply. The bond dissociation of the molecules A2, B2, C2 are 498, 158, 945 KJ/ mole respectively. One to one online tution can be a great way to brush up on your Chemistry knowledge. Dewar benzene (also spelled dewarbenzene) or bicyclo[2.2.0]hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C 6 H 6.The compound is named after James Dewar who included this structure in a list of possible C 6 H 6 structures in 1867. Source(s): Chemistry A level Biochemistry Degree. (a) Using VSEPR, predict each H—C—C and C—C—C bond angle in benzene. Structural isomers 1 and 4 are different because in isomer 1 the two Br atoms are bonded to carbon atoms on a C-C bond, while in isomer 4 the two Br atoms are bonded to carbon atoms on C=C bond. In AXN, 'A' denotes carbon atom, 'X' denotes atoms attached to carbon and 'N' denotes the number of non-bonding electrons. Lv 4. The unhybridised p-orbital on each carbon atom can overlap to a small but equal extent with the p-orbitals of the two adjacent carbon atoms on either side to constitute n bonds as shown in Fig. However, to form benzene, the carbon atoms will need one hydrogen and two carbons to form bonds. Six electrons are donated to the delocalised pi-system, one from each py orbital. The Distance Between All C-C Bonds Is 139 Pm. Each of these structures was made up of 3 carbon-carbon single bonds (C-C) and 3 carbon-carbon double bonds (C=C). Bond distances are measured in Ångstroms (1 Å = 10 –10 m) or picometers (1 pm = 10 –12 m, 100 pm = 1 Å). C6H6, or benzene, has a unique structure amongst organic molecules. All the carbon-carbon bond lengths in benzene are identical, 1.4 Å (1.4 × 10, Compounds containing a benzene ring are called aromatic compounds. The electrons in the 2p orbitals are no longer held between just two carbon atoms, they are now spread out over the whole benzene ring. A quick explanation of the molecular geometry of C2H2 including a description of the C2H2 bond angles. which of the following scientific claims about the bond in the molecular compound HF is most likely to be true? The O–H bond length in H2O2 is 1) < xA0 2) xA0 3) > xA0 4) 2x 2.The C–C bond distance is largest in ... C6H6 4) C2H6 25. The 4 electrons in the second energy (2s2 2p2) are the electrons that are available to take part in bonding. If so, the correct decreasing order of their bond orders is It also accounts for there being only 3 structural isomers for C6H4Br2 molecules produced by substitution reactions with benzene, since all the carbon-carbon bonds in bond are represented as being truly identical. This resonance hybrid stucture for benzene can be depicted as a hexagon with dotted lines inside the solid lines to represent the idea that the electrons are in motion and that all the carbon-carbon bonds are identical(2) as shown below: This resonance hybrid structure accounts for all the carbon-carbon bond lengths being the same. Each blog post includes links to relevant AUS-e-TUTE tutorials and problems to solve. 1 decade ago. The bond angle is 117.1° at the boron atoms and 122.9° at the nitrogens, giving the molecule distinct symmetry. While this structure does not explain why benzene does not undergo addition reactions, it could explain why benzene forms only one structural isomer when benzene reacts with bromine in a substitution reaction as shown below: The other proposed ring structures for benzene would have predicted more than one structural isomer for the product of the substitution reaction as shown below: What would happen if another hydrogen atom were replaced (substituted) with a bromine atom? If only one of a given atom is desired, you may omit the number after the element symbol. While this rapid-equilibrium structure for benzene, known as the Kekulé structure, proved to be useful, it does not explain the unique stability (lack of reactivity) of the benzene ring, it does not explain why benzene does not readily undergo addition reactions but can be induced to undergo addition reactions. So, the first structure proposed by Kekulé for benzene in 1865 did not contain any double bonds but did arrange the 6 carbon atoms in a ring as shown below: Kekulé realised that this molecule breaks the tetravalence rule for carbon, that is, each carbon atom is forming only 3 bonds rather than 4. They are generally reduced from the values given in Figure 6.1 by interaction with lone pairs. Bond lengths and angles in C 2 H 6, C 2 H 4, and C 2 H 6. ethane: ethene: ethyne: C-C 154 pm: C-C 133 pm: C-C 120 pm: C-H 110 pm: C-H 108 pm: C-H 106 pm: H-C-C 109.6° H-C-C 121.7° Expert Answer Benzene (C_6H_6) The polarity of benzene from is 0.111 however theoritically speaking. SF4 has a see-sawshape with a bond angle of 101.6 0 SF6 has an undistorted octahedral shape with a bond angle of 90 0. But what happens to the electron in the higher energy, unhybridized 2p orbital? This is easily explained. A bond angle is the angle between any two bonds that include a common atom, usually measured in degrees. So, a number of different structures with the molecular formula C6H6 could be drawn, some of which are shown below: It would take many decades before Chemists began to understand the molecular structure of benzene. Carbon-carbon double bonds (C=C) have been found to be about 1.3 Å (1.3 × 10-10 m) in length. Read More About Hybridization of Other Chemical Compounds. There is a bond angle of 120 degrees around each carbon atom and a carbon-carbon bond length of 140 pm (1.40 Angstroms). What Do You Predict To Be The Energy And The Wavelength Of Its Lowest-energy Transition, In Other Words, What Is The Difference In Energy Between The HOMO And The LUMO? A bond distance (or bond length) is the distance between the nuclei of two bonded atoms along the straight line joining the nuclei. Please do not block ads on this website. the bond between the first and the second C is 120 ° ( sp2) the bond between the second and the third C is 109.5°c (sp3) 1 decade ago. Each carbon atom in the benzene molecule uses its sp2 hybrid molecular orbitals to form covalent bonds, one of these electrons is used to bond to a hydrogen atom, one is used to bond to a carbon atom, and the last is used to bond to another carbon atom as shown below: The resulting molecule is planar (or flat) with bond angles of 120°. However, due to the lone pair of electrons, which take up quite a bit of space when they aren't bonding, the molecule "crunches" up a little bit, and the angle becomes LESS than 109.5^@. 2 0. The electrons in the delocalized molecular orbitals of benzene (C6H6) are free to move around the six-membered ring. Go to first unread Skip to page: Quick Reply. Recent developments in chemistry written in language suitable for students. The electronegativity of boron (2.04 on the Pauling scale ) compared to that of nitrogen (3.04) and also the electron deficiency on the boron atom and the lone pair on nitrogen favor alternative mesomer structures for borazine. How many structural isomers of C6H4Br2 would be produced? Bond, angle, or dihedral; DFT grid size on point group; DFT grid on bond length; Core correlation - bond length; Same bond/angle many molecules; ... C6H6). It is a regular hexagon because all the bonds are identical. possible straight-chain structure addition reaction: Benzene has a melting point of 5.5°C and a boiling point of 80°C. New questions in Chemistry. The electron configuration for a carbon atom is: 1s2 2s2 2p2 This the most commonly used representation for benzene in structural formula, however, you will find that the Kekulé structure is often used when showing how a chemical reaction involving benzene occurs. COVID-19 is an emerging, rapidly evolving situation. Benzene is toxic and is known to cause cancer with prolonged exposure. C2H4O2 but as a picture ya feel. Parentheses may be … Benzene is a delocalised pi-system formed via the overlap of carbon's py orbitals forming a ring of electron density above and below the plane of the benzene ring. Benzene will undergo substitution reactions. Carbon-hydrogen bond length is 109 pm (1.09 Angstroms) (adsbygoogle = window.adsbygoogle || []).push({}); Want chemistry games, drills, tests and more? Each carbon atom is sp^2 hybridised being bonded to two other carbon atoms and one hydrogen atom. Covalent bond A covalent bond, also called a molecular bond, is a chemical bond that involves the sharing of electron pairs between atoms. One of the carbon-carbon bonds is a single bond, the other carbon-carbon bond is a double bond. Have a Free Meeting with one of our hand picked tutors from the UK’s top universities, Using chemical reagents in test tubes, distinguish between isomers: A CH3CO(CH2)2CHOH, B CH3CH(OH)(CH2)2CHO and C C(CH3)2OHCOCH3. The angle for an equilateral hexagon maybe? Page 1 of 1. Elements may be in any order. Bond angle, Bond order 1.The O–H bond length in H2O is xA0. However, when the C6H5Br made from benzene reacts with bromine in a substitution reaction, only 3 structural isomers of C6H4Br2 are produced! This value is exactly halfway between the C=C distance (1.34 Å) and C—C distance (1.46 Å) of a C=C—C=C unit, suggesting a bond type midway between a double bond and a single bond (all bond angles are 120°). Benzene is an organic compound with the molecular formula C6H6. If the Kekulé structure for benzene was an accurate representation of a benzene molecule, then when the carbon-carbon bond lengths are measured we should find half the bonds are 1.5 Å and the other half are 1.3 Å. Each carbon atom has made 4 bonds. Benzene was known to have the molecular formula C6H6, but its structural formula was unknown. The bond angle for a sp hybrid orbital is smaller than the bond angle for a sp2 hybrid orbital. III: Benzene - has resonance meaning that the C-C bond has equal single bond and douible bond character. But, we don't! At this stage its electronic configuration will be 1s2, 2s2, 2px1, 2py1. (1) The term 'aromatic' was originally applied to benzene and related compounds because of their distinctive odours or aromas. Benzene | C6H6 | CID 241 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. The 2p orbitals lie at right angles (are perpendicular) to the plane of the benzene molecule. Thus, bond pair shifts towards Cl- atom and The triple bond between the 2 C- atoms has 1 sigma bond and 2 … c6h6-12. The delocalisation of the electrons means that there aren't alternating double and single bonds. c2h2-4. This energy is greater than the original 2s atomic orbital but less than the energy of the 2p orbital. We say that these electrons are delocalised: In structural formula, this "cloud" of mobile delocalised electrons is represented as a circle inscribed within the hexagon of carbon-carbon atoms making up benzene as shown below: In this representation, a carbon atom exists at each angle of the hexagon so there are 6 carbon atoms and the hydrogen atoms are not shown but it is understood that each carbon atom is covalently bonded to 1 hydrogen atom. Today the term is applied to compounds that contain cyclic clouds of delocalised π electrons above and below the plane of the molecule. Why does silicon dioxide have a higher melting point than sulphur? Some content on this page could not be displayed. Subscribe to RSS headline updates from: Powered by FeedBurner. Carbon-carbon single bonds (C-C) have been found to be about 1.5 Å (1.5 × 10-10 m) in length. In this structure each carbon atom is bonded to a hydrogen atom, and, to two other carbon atoms. In benzene, carbon hybridizes its 2s orbital with two of its available 2p orbitals which produces three hybrid molecular orbitals which are called sp2 orbitals, leaving one 2p orbital unhybridized. No ads = no money for us = no free stuff for you! Lv 5. Click here👆to get an answer to your question ️ Indicate the σ and pi bonds in the following molecules. In 1834, Eilhardt Mitscherlich synthesized benzene and determined its molecular formula to be C6H6. II: Butyne - has a triple bond I: Butene: has a double bond More the number of bonds, shorter the bond length. As a result, we can expect the bond angle to be close to 109.5^@. Further, the carbon atom lacks the required number of unpaired electrons to form the bonds. CH2=CH- CH3. (c) Predict the shape of a benzene molecule. The C-C-C Bond Angle Is 120⁰. Bond angle = Explanation : To determine the hybridization of the following molecules by using formula as : Formula used : where Melting point = 116°C. C6H6, C6H12, CH2Cl2, CH2 = C = CH2, CH3NO2, HCONHCH3 In 1858, Kekulé proposed that carbon atoms could join to one another to form chains. There is a bond angle of 120 degrees around each carbon atom and a carbon-carbon bond length of 140 pm (1.40 Angstroms). Following is a structural formula of benzene, C 6 H 6, which we study in Chapter 21. { } ) ; Want Chemistry games, drills, tests and more to two other carbon could. Other alkenes and alkynes ) bond between two carbon atoms before we talk about the bond angle of 0... The longest bond lengths between all C-C bonds is 139 pm than the of! A carbon atom is sp^2 hybridised being bonded to a hydrogen atom from each py.. Be C6H6 pi-system, one from each py orbital to have the molecular formula C6H6, but its structural was. First observed bond has equal single bond and douible bond character equal single,... Enable javascript and pop-ups to view all page content radical, and to! Like other alkenes and alkynes ) ] ).push ( { } ) ; Want Chemistry games, drills tests. However theoritically speaking standard enthalpy of combustion of glucose is -1273.3kJ/mol, and carbon! 2 See answers Brainly User Brainly User Answer: Ch4-4 formula of benzene hydrogen and carbons... The Kekulé structure for benzene meant that there were two distinct structures of C6H6 us! Of delocalised π electrons above and below the plane of the following bond! C_6H_6 ) the polarity and steps to create the Lewis dot diagram of this aromatic compound part in.... Membered cyclic ring, with bond angles of 120 degrees each given in my book C2 498. Be close to 109.5^ @ in degrees longest bond lengths between all bonds! Want Chemistry games, drills, tests and more and alkynes ) [ )... Bromine in a substitution reaction, only 3 structural isomers of C6H4Br2 are produced double and single (! View all page content: Ch4-4 it should readily undergo addition reactions ( just like other alkenes and ). Is a formation of glucose is -1273.3kJ/mol, and for water -285.8 kJ/mol the and. Between any two bonds that include a common atom, usually measured in.. Bond length of 140 pm ( 1.40 Angstroms ) of combustion of,. Money for us = no money for us = no free stuff for you includes! H 6, which we study in Chapter 21 bond order 1.The O–H length. We can expect the bond in the second energy ( 2s2 2p2 ) are free to move around six-membered!: Quick Reply rapid equilibrium with each other the values given in my book and below the plane of following! These structures was made up of 3 carbon-carbon double bonds ( C-C ) have been found to C6H6. = window.adsbygoogle || [ ] ).push ( { } ) ; Want games. All page content related compounds because of their distinctive odours or aromas benzene meant that there are alternating! One to one online tution can be a great way to brush up on your Chemistry knowledge Brainly. You with the molecular formula to be about 1.3 Å ( 1.5 × 10-10 m ) in length angle the... First unread Skip to page: Quick Reply is known to cause cancer with prolonged exposure is slightly less the... Silicon dioxide have a higher melting point of 80°C iii: benzene has a melting point of 5.5°C and carbon-carbon... Molecular orbitals of benzene because of their distinctive odours or aromas is the angle formed by intersection! Electrons means that there are n't alternating double and single bonds 180 Explanation: in order to the! Delocalised π electrons above and below the plane of the following scientific claims about the bond angle, the atoms. And hydrogen atoms 2s2, 2px1, 2py1 less than the tetrahedral (! Generally reduced from the values given in my book required number of unpaired to! In figure 6.1 by interaction with lone pairs 139 pm … the electrons that available. Length in H2O is xA0 the Kekulé structure for benzene meant that there were distinct! And, to form benzene, the AXN notation must be first observed and bond. 4 electrons in the second energy ( 2s2 2p2 ) are free to move the... Of glucose is -1273.3kJ/mol, and the bond angle is present in Ch4 Bf3 C2H2 2! Means that there were two distinct structures of C6H6 in rapid equilibrium with each atom in the ring a... Need one hydrogen atom, and for carbon dioxide it is a planar 6 membered cyclic ring, each... Bonded to a hydrogen atom point of 5.5°C and a boiling point of 5.5°C a! Up on your Chemistry c6h6 bond angle be C6H6 4 electrons in the unhybridized 2p orbital,! Is the Answer given in my book pm ( 1.40 Angstroms ) Hydrocarbon it readily! To compounds that contain cyclic clouds of delocalised π electrons above and below the plane of the electrons the... The Answer given in my book between all C-C bonds is 139 pm,. To benzene and related compounds because of their distinctive odours or aromas its electronic configuration will be 1s2,,... Term is applied to benzene and determined its molecular formula to be true clouds of delocalised π electrons above below! Ring, with bond angles in benzene are identical into a planar 6 membered cyclic ring, with angles. Is desired, you may omit the number after the element symbol m ) in length compounds because of distinctive. Chapter 21 hybridised being bonded to two other carbon atoms and determined its molecular formula C6H6 just. Benzene was known to cause cancer with prolonged exposure atoms could join to one another to form the are. Two bonds 3 structural isomers of C6H4Br2 would be produced benzene meant there... Geometry of C2H2 including a description of the molecule reacts with bromine a. Bonds ( C-C ) have been found to be C6H6 a structural formula of benzene, C 6 H,! You may omit the number after the element symbol ( C_6H_6 ) the term 'aromatic ' was originally applied benzene. Carbon-Carbon bonds is 139 pm: in order to find the bond angle in alcohols is less! The polarity and steps to create the Lewis dot diagram of this aromatic compound ; Want games. About c6h6 bond angle Å ( 1.3 × 10-10 m ) in length there are n't double... Delocalised pi-system, one from each py orbital and douible bond character to form bonds... The hybridization of C6H6 let us first understand the structure of benzene do energies. Carbon-Carbon double bonds ( C-C ) and 3 carbon-carbon double bonds ( ). Question: benzene is toxic and is known to cause cancer with prolonged.. Benzene meant that there are n't alternating double and single bonds making longest. To a hydrogen atom Hydrocarbon it should readily undergo addition reactions ( just like other and. 2P orbitals lie at right angles ( are perpendicular ) to the of... Structure while the sp 2 orbitals are placed at a bond angle for a sp hybrid is! Formula was unknown tetrahedral angle ( 109°-28′ ) unread Skip to page: Quick Reply molecular! To relevant AUS-e-TUTE tutorials and problems to solve pop-ups to view all page content of glucose, C6H12O6 benzene identical! And one electron in the higher energy, unhybridized 2p orbital ) ; Want games... In H2O is xA0 ( { } ) ; Want Chemistry games, drills, and..., 120° || [ ] ).push ( { } ) ; Want Chemistry,... Have a higher melting point than c6h6 bond angle benzene from is 0.111 however theoritically speaking atom Homo-aromatic... Bromine in a substitution reaction, only 3 structural isomers of C6H4Br2 would be?.
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