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di-p-toluoyl-L-tartaric acid

Input interpretation

di-p-toluoyl-L-tartaric acid
di-p-toluoyl-L-tartaric acid

Chemical names and formulas

formula | [-CH(COOH)OCOC_6H_4(CH_3)]_2 Hill formula | C_20H_18O_8 name | di-p-toluoyl-L-tartaric acid IUPAC name | (2S, 3S)-2, 3-bis[(4-methylphenyl)-oxomethoxy]butanedioic acid alternate names | 2, 3-bis[(4-methylbenzoyl)oxy]succinic acid | (2S, 3S)-2, 3-bis[(4-methylbenzoyl)oxy]butanedioic acid | (2S, 3S)-2, 3-bis[(4-methylbenzoyl)oxy]succinic acid | (2S, 3S)-2, 3-bis[(4-methylphenyl)carbonyloxy]butanedioic acid | (+)-di-o-4-toluoyl-D-tartaric acid | (+)-di-O, O'-p-toluyl-D-tartaric acid mass fractions | C (carbon) 62.2% | H (hydrogen) 4.7% | O (oxygen) 33.1%
formula | [-CH(COOH)OCOC_6H_4(CH_3)]_2 Hill formula | C_20H_18O_8 name | di-p-toluoyl-L-tartaric acid IUPAC name | (2S, 3S)-2, 3-bis[(4-methylphenyl)-oxomethoxy]butanedioic acid alternate names | 2, 3-bis[(4-methylbenzoyl)oxy]succinic acid | (2S, 3S)-2, 3-bis[(4-methylbenzoyl)oxy]butanedioic acid | (2S, 3S)-2, 3-bis[(4-methylbenzoyl)oxy]succinic acid | (2S, 3S)-2, 3-bis[(4-methylphenyl)carbonyloxy]butanedioic acid | (+)-di-o-4-toluoyl-D-tartaric acid | (+)-di-O, O'-p-toluyl-D-tartaric acid mass fractions | C (carbon) 62.2% | H (hydrogen) 4.7% | O (oxygen) 33.1%

Lewis structure

Draw the Lewis structure of di-p-toluoyl-L-tartaric acid. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds:  Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), and oxygen (n_O, val = 6) atoms: 20 n_C, val + 18 n_H, val + 8 n_O, val = 146 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): 20 n_C, full + 18 n_H, full + 8 n_O, full = 260 Subtracting these two numbers shows that 260 - 146 = 114 bonding electrons are needed. Each bond has two electrons, so in addition to the 47 bonds already present in the diagram add 10 bonds. To minimize formal charge oxygen wants 2 bonds and 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: |   |
Draw the Lewis structure of di-p-toluoyl-L-tartaric acid. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), and oxygen (n_O, val = 6) atoms: 20 n_C, val + 18 n_H, val + 8 n_O, val = 146 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): 20 n_C, full + 18 n_H, full + 8 n_O, full = 260 Subtracting these two numbers shows that 260 - 146 = 114 bonding electrons are needed. Each bond has two electrons, so in addition to the 47 bonds already present in the diagram add 10 bonds. To minimize formal charge oxygen wants 2 bonds and 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: | |

3D structure

3D structure
3D structure

Basic properties

molar mass | 386.36 g/mol phase | solid (at STP) melting point | 170 °C solubility in water | insoluble
molar mass | 386.36 g/mol phase | solid (at STP) melting point | 170 °C solubility in water | insoluble

Units

Chemical identifiers

CAS number | 32634-68-7 Beilstein number | 3225584 PubChem CID number | 263211 PubChem SID number | 24858275 SMILES identifier | CC1=CC=C(C=C1)C(=O)OC(C(C(=O)O)OC(=O)C2=CC=C(C=C2)C)C(=O)O InChI identifier | InChI=1/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10, 15-16H, 1-2H3, (H, 21, 22)(H, 23, 24)/t15-, 16-/m0/s1/f/h21, 23H MDL number | MFCD00008552
CAS number | 32634-68-7 Beilstein number | 3225584 PubChem CID number | 263211 PubChem SID number | 24858275 SMILES identifier | CC1=CC=C(C=C1)C(=O)OC(C(C(=O)O)OC(=O)C2=CC=C(C=C2)C)C(=O)O InChI identifier | InChI=1/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10, 15-16H, 1-2H3, (H, 21, 22)(H, 23, 24)/t15-, 16-/m0/s1/f/h21, 23H MDL number | MFCD00008552

NFPA label

NFPA label
NFPA label
NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0
NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0

Toxicity properties

odor | odorless
odor | odorless