An organic compound (with an index of hydrogen deficiency of 1), containing only carbon, hydrogen, and oxygen was burned in excess oxygen. When 12.915 g of the organic compound is burned, this produced 18.942 g carbon dioxide and 7.749 g of water. The organic compound was reacted with 3 moles of trimethylsilyl chloride (TMSCI) as protecting agent (used to protect alcohols and amines to convert them to trimethylsilyl ethers and trimethylsilyl amines; it can also react with carboxylic acid and water). Chemical tests using 2,4-dinitrophenyl hydrazine and Tollens reagent both resulted to negative results. The IR spectrum for the compound (in KBr disk) is shown below. L00 S000 2000 1000 KAVENUNB ERI Propose the structure for the compound that best fits these data. Illustrate the orbitals involved for the electronic transitions for this compound, consider different types of chromophore.

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An organic compound (with an index of hydrogen deficiency of 1), containing only carbon, hydrogen,
and
oxygen was burned in excess oxygen. When 12.915 g of the organic compound is burned, this
produced 18.942 g carbon dioxide and 7.749 g of water. The organic compound was reacted with 3
moles of trimethylsilyl chloride (TMSCI) as protecting agent (used to protect alcohols and amines to
convert them to trimethylsilyl ethers and trimethylsilyl amines; it can also react with carboxylic acid
and water). Chemical tests using 2,4-dinitrophenyl hydrazine and Tollens reagent both resulted to
negative results. The IR spectrum for the compound (in KBr disk) is shown below.
L00
SD
D
4D00
3000
2000
1500
1000
SDO
NAVENUHBERIl
Propose the structure for the compound that best fits these data. Illustrate the orbitals involved for
the electronic transitions for this compound, consider different types of chromophore.
TEANSHITTANCETST
Transcribed Image Text:An organic compound (with an index of hydrogen deficiency of 1), containing only carbon, hydrogen, and oxygen was burned in excess oxygen. When 12.915 g of the organic compound is burned, this produced 18.942 g carbon dioxide and 7.749 g of water. The organic compound was reacted with 3 moles of trimethylsilyl chloride (TMSCI) as protecting agent (used to protect alcohols and amines to convert them to trimethylsilyl ethers and trimethylsilyl amines; it can also react with carboxylic acid and water). Chemical tests using 2,4-dinitrophenyl hydrazine and Tollens reagent both resulted to negative results. The IR spectrum for the compound (in KBr disk) is shown below. L00 SD D 4D00 3000 2000 1500 1000 SDO NAVENUHBERIl Propose the structure for the compound that best fits these data. Illustrate the orbitals involved for the electronic transitions for this compound, consider different types of chromophore. TEANSHITTANCETST
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