Carbon suboxide, \(\mathrm{C}_{3} \mathrm{O}_{2}\), is a linear molecule with the two oxygen atoms at the end and double bonds between each carbon and oxygen atom.
a. Draw the Lewis structure for \(\mathrm{C}_{3} \mathrm{O}_{2}\).
b. State the type of hybridization of each carbon atom.
c. Calculate the heat of reaction for the reaction of carbon suboxide with water to form malonic acid \(\left(\mathrm{HO}_{2} \mathrm{CCH}_{2} \mathrm{CO}_{2} \mathrm{H}\right)\). Hint: Each end of malonic acid has a carbon double bonded to an oxygen and to a hydroxide.
Text Transcription:
C_3O_2
(HO_2CCH_2CO_2H)
Organic Chemistry Professor Gorden (9/18-9/22 Notes) Monday’s Notes: (Ch. 5: Stereochemistry) o Isomers: nonidentical compounds have the same molecular formula o Stereoisomers: isomers that contain the same atoms and same connectivity but differ in how atoms are arranged in space o C-C bonds that are constrained in a cyclic structure can’t freely rotate o Thalidomide: why chirality matters Thalidomide: sedative resulted in severe birth defects only because the S and R isomers or enantiomers given as a mixture. Pure R form would probably have not created a problem Thalidomide S enantiomers is now being used to treat MS Must be avoided by women being treated of child-bearing age R and S are a way to designate the specific nature of a special kind of isomerism involving the “handedness” of molecules called stereoisomerism o Handedness Chirality: whether something has “handedness” All sorts of common objects are chiral The interactions between a chiral object and two enantiomers are different We are concerned with chirality because natural products are often chiral This holds for complex enzymatic systems and the simpler building blocks of life Proteins, amino acids, and sugars are
