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Ejercicios para estudiar los temas del examen.
ISOMERÍA
Ejercicios para estudiar los temas del examen. PROBLEM 1-30 Convert the following molecular formulas into line-bond structures that are consistent with valence rules: (a) CaHz (b) CH5N (c) C2H50 (2 possibilities) (d) CaH7Br (2 possibilities) (e) C2H40 (3 possibilities) (f) CaHaN (4 possibilities) PROBLEM 1-32 Oxaloacetic acid, an important intermediate in food metabolism, has the formula C¿H405 and contains three C =0 bonds and two O-H bonds. Propose two possible structures. Hybridization PROBLEM 1-34 What is the hybridization of each carbon atom in acetonitrile (Problem 1-26)? PROBLEM 1-38 Propose structures for molecules that meet the following descriptions: (a) Contains two sp?-hybridized carbons and two sp*-hybridized carbons (b) Contains only four carbons, all of which are sp*-hybridized (c) Contains two sp-hybridized carbons and two sp*-hybridized carbons PROBLEM 1-39 What kind of hybridization do you expect for each carbon atom in the following molecules: la) Calculate the formal charges on the atoms shown in red. (a) . (CH3)20BF3 (b) .. H2C—N=N: (e) es H¿C=N=N: Mar s0= —-0: (e) có H2C—P—CH3 | CH3 0 ISOMERÍA 3-38 Give IUPAG names for the following compounds: (a) 6) cua CH¿CHCH¿CH2CH3 (> (6) oia CHCH2CCH CHy (e) e HC Cia CH3CHCCH¿CH2CH CH3 Ls CHaCHa Cha CH¿CH2CHCH2CHCHCH3 (8) te CH¿ CH2CHy CHgoiaCHaCHCHACCH CHa ll H3C CHy CH¿C—CCH¿CH2CH3 H3C CHa PROBLEM 3-53 The cholesterol-lowering agents called statins, such as simvastatin (Zocor) and pravastatin (Pravachol), are among the most widely prescribed drugs in the world, with annual sales estimated at approximately $25 billion. Identify the functional groups in both, and tell how the two substances differ. o A HO. o s Ho. 0H o OH o o o O CH3 CH aC HO Simvastatin Pravastatin (Zocor) (Pravachol) PROBLEM 7-37 Name the following alkenes: (a) CH3 A CHCH2CHa CH3 CH2CHg CH¿CHCH¿CH2CH—— CHa t=C PON, Had H ta AO H3C ct=C de H7C= cHcHH H CH3 (e) H3C t=C A, Y, p< CH3 CH3CH¿CH2 — CH3 PROBLEM 7-49 trans-2-Butene is more stable than cís-2-butene by only 4 kJ/mol, but trans-2,2,5,5-tetramethyl-3-hexene is more stable than its cis isomer by 39 kJ/mol. Explain. PROBLEM Erythronolide B is the biological precursor of erythromycin, a broad-spectrum antibioti centers does erythronolide B have? Identify them. HC. CH 0H H3Ca Ha Erythronolide B HC 0H “OH PROBLEM 5-36 How many chirality 5-37 Which of the following pairs of structures represent the same enantiomer, and which represent different enantiomers? (a a (5) Doe oa PROBLEM 5-38 What is the relationship between the specific rotations of (2R,8A)-dichloropentane and (25,38)- dichloropentane? Between (2R,38)-dichloropentane and (2R,3A)-dichloropentane? PROBLEM 5-43 Assign A or S configurations to each chiralty center in the following molecules: (el H do cl Y a HocH2 02H prose 5-44 Assign Mor S confguration to each cairality center in the following moleculas: