Question

5. Student X obtained an organic compound A (CSH) and wishes to know its structure. He did three experiment and the results are shown as below: Ex. 1: Pd/C, H2 A(C18H24) C15H28 Ex. 2 1. O3, CH2Cl2 2. Zn, acetic acid 2. Zn, acetic acid онол + formaldehyde Ex. 3: 1.1.0 eq. BH3. THE 2. NaOH, H2O2 1. 03. CH CI2 2. DMS A онсы HO Based on the information, please answer: a. What's the structure of A and B? b. What is the absolute configuration of the marked carbon (), which is not indicated in the picture?

Answer 1

[Answer 1) molecular bormula ols Compound A is 45424. The molecular Loormula indicate Compound A have 4-degree ols unsatura hon. 1) Experiment 1: The cataly hic hydrogenalan ols Compound a give compound with molecular loomula C15 H28. The adclinicom ols two molar equivalent hydrogen molecule indicate Compound A have two ac bood. These two c=c band represent two degree of unsatura hon- 3) Experiment 2 compound Am Ozonoly si's give Product kormaldehyde and Other product, which contain two ketone and one aldehyde. This indicate Compound A is bicyclic Compound. The Lormation os Formaldehyde indicate one double bond is present en ring." - The Possible structure als Compound A y H₂ led-c Exp-1 CASH28 (15H24 11-0₂ 1erbela 2. Znlay-coon

Experiment -9 1. leq 3413. THE 2. Naoh 4602 -OH 1-O3, C4Cl2 2.oms HO a) Structure ols A and B A Ho B] (b) Absolute conleiguration of the marked Carbon ( S- Con Ligurahioms