name of (-)-6,6'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene

(-)-6, 6'-dibromo-2, 2'-bis(methoxymethoxy)-1, 1'-binaphthalene

molar mass | 532.2 g/mol formula | C_24H_20Br_2O_4 empirical formula | Br_C_12O_2H_10 SMILES identifier | COCOC1=C(C2=CC=C(C=C2C=C1)Br)C3=C(C=CC4=CC(=CC=C43)Br)OCOC InChI identifier | InChI=1/C24H20Br2O4/c1-27-13-29-21-9-3-15-11-17(25)5-7-19(15)23(21)24-20-8-6-18(26)12-16(20)4-10-22(24)30-14-28-2/h3-12H, 13-14H2, 1-2H3 InChI key | UPLLZDVWXACTEG-UHFFFAOYSA-N

Draw the Lewis structure of (-)-6, 6'-dibromo-2, 2'-bis(methoxymethoxy)-1, 1'-binaphthalene. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the bromine (n_Br, val = 7), carbon (n_C, val = 4), hydrogen (n_H, val = 1), and oxygen (n_O, val = 6) atoms: 2 n_Br, val + 24 n_C, val + 20 n_H, val + 4 n_O, val = 154 Calculate the number of electrons needed to completely fill the valence shells for bromine (n_Br, full = 8), carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): 2 n_Br, full + 24 n_C, full + 20 n_H, full + 4 n_O, full = 280 Subtracting these two numbers shows that 280 - 154 = 126 bonding electrons are needed. Each bond has two electrons, so in addition to the 53 bonds already present in the diagram add 10 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 10 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |

melting point | 489 °C boiling point | 818.6 °C critical temperature | 1352 K critical pressure | 1.751 MPa critical volume | 1204 cm^3/mol molar heat of vaporization | 103 kJ/mol molar heat of fusion | 53.01 kJ/mol molar enthalpy | -229 kJ/mol molar free energy | 140.2 kJ/mol (computed using the Joback method)

longest chain length | 12 atoms longest straight chain length | 4 atoms longest aliphatic chain length | 0 atoms aromatic atom count | 20 atoms H-bond acceptor count | 2 atoms H-bond donor count | 0 atoms

Find the elemental composition for (-)-6, 6'-dibromo-2, 2'-bis(methoxymethoxy)-1, 1'-binaphthalene in terms of the atom and mass percents: atom percent = N_i/N_atoms × 100% mass percent = (N_im_i)/m × 100% Plan: • Write the chemical formula and gather atomic masses from the periodic table. • Determine values for N_i, m_i, N_atoms and m using these items. • Finally, compute the percents and check the results. Write the chemical formula: C_24H_20Br_2O_4 Use the chemical formula to count the number of atoms, N_i, for each element and find the total number of atoms, N_atoms, per molecule: | number of atoms Br (bromine) | 2 C (carbon) | 24 O (oxygen) | 4 H (hydrogen) | 20 N_atoms = 2 + 24 + 4 + 20 = 50 Divide each N_i by N_atoms to calculate atom fractions. Then use the property that atom fractions must sum to one to check the work: | number of atoms | atom fraction Br (bromine) | 2 | 2/50 C (carbon) | 24 | 24/50 O (oxygen) | 4 | 4/50 H (hydrogen) | 20 | 20/50 Check: 2/50 + 24/50 + 4/50 + 20/50 = 1 Compute atom percents using the atom fractions: | number of atoms | atom percent Br (bromine) | 2 | 2/50 × 100% = 4.00% C (carbon) | 24 | 24/50 × 100% = 48.0% O (oxygen) | 4 | 4/50 × 100% = 8.00% H (hydrogen) | 20 | 20/50 × 100% = 40.0% Look up the atomic mass, m_i, in unified atomic mass units, u, for each element in the periodic table: | number of atoms | atom percent | atomic mass/u Br (bromine) | 2 | 4.00% | 79.904 C (carbon) | 24 | 48.0% | 12.011 O (oxygen) | 4 | 8.00% | 15.999 H (hydrogen) | 20 | 40.0% | 1.008 Multiply N_i by m_i to compute the mass for each element. Then sum those values to compute the molecular mass, m: | number of atoms | atom percent | atomic mass/u | mass/u Br (bromine) | 2 | 4.00% | 79.904 | 2 × 79.904 = 159.808 C (carbon) | 24 | 48.0% | 12.011 | 24 × 12.011 = 288.264 O (oxygen) | 4 | 8.00% | 15.999 | 4 × 15.999 = 63.996 H (hydrogen) | 20 | 40.0% | 1.008 | 20 × 1.008 = 20.160 m = 159.808 u + 288.264 u + 63.996 u + 20.160 u = 532.228 u Divide the mass for each element by m to calculate mass fractions. Then use the property that mass fractions must sum to one to check the work: | number of atoms | atom percent | mass fraction Br (bromine) | 2 | 4.00% | 159.808/532.228 C (carbon) | 24 | 48.0% | 288.264/532.228 O (oxygen) | 4 | 8.00% | 63.996/532.228 H (hydrogen) | 20 | 40.0% | 20.160/532.228 Check: 159.808/532.228 + 288.264/532.228 + 63.996/532.228 + 20.160/532.228 = 1 Compute mass percents using the mass fractions: Answer: | | | number of atoms | atom percent | mass percent Br (bromine) | 2 | 4.00% | 159.808/532.228 × 100% = 30.03% C (carbon) | 24 | 48.0% | 288.264/532.228 × 100% = 54.16% O (oxygen) | 4 | 8.00% | 63.996/532.228 × 100% = 12.02% H (hydrogen) | 20 | 40.0% | 20.160/532.228 × 100% = 3.788%

The first step in finding the oxidation states (or oxidation numbers) in (-)-6, 6'-dibromo-2, 2'-bis(methoxymethoxy)-1, 1'-binaphthalene is to draw the structure diagram. Next set every oxidation number equal to the atom's formal charge: In (-)-6, 6'-dibromo-2, 2'-bis(methoxymethoxy)-1, 1'-binaphthalene hydrogen is not bonded to a metal with lower electronegativity, so it will have an oxidation state of +1. Any element bonded to hydrogen gains the bonding electrons, decreasing their oxidation state by 1 for every bond: With hydrogen out of the way, look at the remaining bonds. There are 2 bromine-carbon bonds, 8 carbon-oxygen bonds, and 23 carbon-carbon bonds. For each of these bonds, assign the bonding electrons to the most electronegative element. First examine the bromine-carbon bonds: element | electronegativity (Pauling scale) | Br | 2.96 | C | 2.55 | | | Since bromine is more electronegative than carbon, the electrons in these bonds will go to bromine. Decrease the oxidation number for bromine in every highlighted bond (by 1 for single bonds, 2 for double bonds, and 3 for triple bonds), and increase the oxidation number for carbon accordingly: Next look at the carbon-oxygen bonds: element | electronegativity (Pauling scale) | C | 2.55 | O | 3.44 | | | Since oxygen is more electronegative than carbon, the electrons in these bonds will go to oxygen: Next look at the carbon-carbon bonds: element | electronegativity (Pauling scale) | C | 2.55 | C | 2.55 | | | Since these elements are the same the bonding electrons are shared equally, and there is no change to the oxidation states: Now summarize the results: Answer: | | oxidation state | element | count -2 | C (carbon) | 2 | O (oxygen) | 4 -1 | Br (bromine) | 2 | C (carbon) | 10 0 | C (carbon) | 8 +1 | C (carbon) | 4 | H (hydrogen) | 20

First draw the structure diagram for (-)-6, 6'-dibromo-2, 2'-bis(methoxymethoxy)-1, 1'-binaphthalene, and for every non-hydrogen atom, count the σ-bonds. Note that double and triple bonds consist of one σ-bond together with one or two π-bonds: Identify those atoms with lone pairs: Find the steric number by adding the lone pair count to the number of σ-bonds: Consult the following chart to determine the hybridization from the steric number: steric number | hybridization 2 | sp 3 | sp^2 4 | sp^3 5 | dsp^3 6 | d^2sp^3 7 | d^3sp^3 Assign the provisional hybridization based on the table: Next identify any sp^3 atoms with lone pair electrons which can participate in a conjugated π-bond system. These atoms can lower their energy by placing a lone pair in a unhybridized p orbital to maximize overlap with the neighboring π-bonds. Note that halogens and elements from the third period and below do not engage in bond conjugation, except in the case of aromaticity: Adjust the provisional hybridizations to arrive at the result: Answer: | |

vertex count | 50 edge count | 53 Schultz index | 30836 Wiener index | 7645 Hosoya index | (data not available) Balaban index | 2.02