Chapter 8.5, Problem 8.10E

(a)

Interpretation Introduction

Interpretation: The expected reactant that can yield $\text{1-decanol}$ as product of ${\text{NaBH}}_{\text{4}}$ reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

  

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of $\text{B-H}$ bond towards carbonyl carbon as illustrated below;

  

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation:The expected reactant that can yield $\text{4-methyl-2-pentanol}$ as product of ${\text{NaBH}}_{\text{4}}$ reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

  

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of $\text{B-H}$ bond towards carbonyl carbon as illustrated below;

  

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(c)

Interpretation Introduction

Interpretation:The expected reactant that can yield cyclopentylmethanol asproduct of ${\text{NaBH}}_{\text{4}}$ reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

  

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of $\text{B-H}$ bond towards carbonyl carbon as illustrated below;

  

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.

(d)

Interpretation Introduction

Interpretation:The expected reactant that can yield $1,4\text{-cyclohexanediol}$ as product of ${\text{NaBH}}_{\text{4}}$ reduction should be formulated.

Concept introduction:The carbonyl bond is polar with partial positive charge on carbon and partial negative charge on oxygen as illustrated below.

  

Thus it can undergo hydride addition at carbon and proton addition at oxygen. Certain reagents that are useful for such hydride addition at carbonyl carbon include sodium borohydride, lithium aluminum hydride. The boron and lithium in these reagents tend to push the electron of $\text{B-H}$ bond towards carbonyl carbon as illustrated below;

  

Any organic compound must have no plane of symmetry in order to be chiral or optically active. The compounds with any plane of symmetry are achiral and optically inactive.