Question

The following synthesis is done in 3 steps.
1. The selective oxidation of alcohols.
2. Aromatic Grignard
3. Carbon-Carbon coupling.

Perform stoichiometric calculations to obtain 1 ml of the final product, using the concept of limit reagent in the synthesis of geranial and phenylmagnesium bromide. assuming 100% yield.

MgBr 115-hed CH3 Hąc OH H3C/ CHz Geranial Phenylmagnesium bromide ???

The complete equations of the synthesis of geranial and grignard reagent are shown below. (They are needed to calculate the final 1 ml of product of the reaction above)

CH3 OH PCC DCM H₂C CH₂ H2C CH3 Geraniol Geranial

MgBr THE Mg, 1 Bromobenzene Phenylmagnesium bromide

Density of Final Product: 0.962 g/cm3

Molecular weight of Final Product: 230.35

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Answer #1

The name of the product is (E)-3,7-dimethyl-1-phenylocta-2,6-dien-1-ol.

The moles of product = (1 mL * 0.962 g/mL)/(230.35 g.mol-1) = 0.004176 mol

i.e. The moles of geraniol required = 0.004176 mol

i.e. The mass of geraniol required = 0.004176 mol * 154.25 g/mol = 0.644 g

Then, the mass of geranial produced = 0.004176 mol * 152.24 g/mol = 0.636 g

And the moles of bromobenzene required = 0.004176 mol

i.e. The mass of bromobenzene required = 0.004176 mol * 157.01 g/mol = 0.656 g

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