Question

Camphor (C10H16O${\text{C}}_{\mathrm{₁₀}}^{}{\text{H}}_{\mathrm{₁₆}}^{}\text{O}$) is a natural compound found in the wood of camphor laurel, an evergreen native to southeast Asia. Borneol (C10H18O${\text{C}}_{\mathrm{₁₀}}^{}{\text{H}}_{\mathrm{₁₈}}^{}\text{O}$) and isoborneol (C10H18O${\text{C}}_{\mathrm{₁₀}}^{}{\text{H}}_{\mathrm{₁₈}}^{}\text{O}$) are similar to camphor, but are alcohols instead of a ketone. The difference between borneol and isoborneol is the stereogenic arrangement of the hydroxyl group. Analyze the 3‑D models of each compound and predict the major product or products when camphor participates in the reactions shown.

Camphor reacts with H_{$2_{}^{}$} and N$i$ to form:

□ Borneol

□ Isoborneol

Camphor reacts with (1) L${\text{iAlH}}_{\mathrm{₄}}^{}$ and (2) (CH3)2CHOH${({\text{CH}}_{\mathrm{₃}}^{})}_{\mathrm{₂}}^{}\text{CHOH}$ to form:

    □ Isoborneol

    □ Borneol

Answer 1

Camphor reacts with H_{$2_{}^{}$} and N$i$ to form:

Ans: Both    

□√ Borneol

□√ Isoborneol

Camphor reacts with (1) L${\text{iAlH}}_{\mathrm{₄}}^{}$ and (2) (CH3)2CHOH${({\text{CH}}_{\mathrm{₃}}^{})}_{\mathrm{₂}}^{}\text{CHOH}$ to form:

 

Ans: □√ Isoborneol