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PROBLEMAS DE QUMICA ORGNICA I

LECCIN 2. ESTRUCTURA Y ENLACES Problem 1.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.7) Write Lewis structures, including unshared pairs, for each of the following. Carbon has four single bonds in each compound a) Propane (C3H8) b) Methanol (CH4O) c) Methyl fluoride (CH3F) d) Ethyl fluoride (C2H5F)

Problem 2.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.8) All the hydrogens are bonded to carbon in both of the following compounds. Write a Lewis structure that satisfies the octet rule for each. a) Formaldehide (CH2O) b) Hydrogen cyanide (HCN)

Problem 3.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.9) In which of the compounds CH4, NH3, H2O, SiH4, or H2S is + for hydrogen the greatest? In which one does hydrogen bear a partial negative charge?

Problem 4.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.10) Write structural formulas for all the constitutional isomers that have the given molecular formula. a) C2H7N b) C3H7Cl c) C3H8O

Problem 5.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.13) Like nitric acid, each of the following inorganic compounds will be frequently encountered in the Organic Chemistry texts. Calculate the formal charge on each of the atoms in the Lewis structures given. a) b) c)

Thionyl chloride

Sulfuric acid

Nitrous acid

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Problem 6.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.16) Nitrite ion (NO2) has the connectivity O-N-O. Write two Lewis structures for nitrite ion that obey the octect rule. Do the two contribute equally to the resonance hybrid?

Problem 7.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.17) Apply the resonance concept to explain why all the CO bond distances in carbonate ion (CO3) are equal.

Problem 8.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.18) Write the resonance structures obtained by moving electrons as indicated by the curved arrows. Compare the stabilities of the two resultant Lewis structures. a) c)

b)

d)

Problem 9.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.21) Which of the following compounds would you expect to have a dipole moment? If the molecule has a dipole moment, specify its direction. a) BF3 b) H2O c) CH4 d) CH3Cl e) CH2O f) HCN

Problem 10.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.39; Soluc. 5 Ed. 1.23) Each of the following species will be encountered at some point in this text. They all have the same number of electrons binding the same number of atoms and the same

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arrangement of bonds; they are isoelectronic. Specify which atoms, if any, bear a formal charge in the Lewis structure given and the net charge for each species. (a) :N N: (b) :C N: (c) :C C: (d) :N O: (e) :C O:

Problem 11.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.40; Soluc. 5 Ed. 1.24) You will meet all the following isoelectronic species in this text. Repeat the previous problema for these three structures.

Problem 12.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.41; Soluc. 5 Ed. 1.25)

Problem 13.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.45; Soluc. 5 Ed. 1.29)

Problem 14.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.46; Soluc. 5 Ed. 1.30)

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Problem 15.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.47; Soluc. 5 Ed. 1.31)

Problem 16.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.48; Soluc. 5 Ed. 1.32)

Problem 17.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.49; Soluc. 5 Ed. 1.33)

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Problem 18.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.50; Soluc. 5 Ed. 1.34)

Problem 19.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.51; Soluc. 5 Ed. 1.35)

Problem 20.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.55; Soluc. 5 Ed. 1.39)

Problem 21.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.56; Soluc. 5 Ed. 1.40)

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Problem 22.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.57; Soluc. 5 Ed. 1.41)

Problem 23.- (Qum. Org., F. Carey, 6 Ed.; Problema 1.62; Soluc. 5 Ed. 4.29)

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