Chapter 8.13, Problem 31PTS

(a)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

• Hydroboration-oxidation reaction: Addition of $\text{–H and –OH}$ group across the double bond in presence of borane and hydrogen peroxide with base is known as hydroboration-oxidation reaction.  It follows Anti-Markovnikov addition.

• Anti-Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

  

(b)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

Catalytic hydrogenation:   It is the addition of molecular hydrogen across triple bond in presence of platinum catalyst.  This catalyst helps to reduce alkyne to alkane.

(c)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

Anti-dihydroxylation: In this reaction alkene reacts with peroxy acid and gives an epoxide.  Further, the epoxide undergoes an acid-catalyzed opening to form a trans diol.

(d)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

Syn-dihydroxylation: In this reaction alkene reacts with osmium tetroxide and gives an osmate ester.  Further, the osmate ester treated with sodium bisulfate to form a cisdiol.

(e)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

• Simple hydration in acidic media gives the addition product through carbocation intermediate and follows Markovnikov addition.
• An acid-catalysed hydration is shown below.

  

(f)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

Hydro-halogenation reaction: In this reaction, hydrogen halide added across the unsaturated bond (alkene) via Markovnikov’s addition.

Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

(g)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

Anti-dihydroxylation: In this reaction alkene reacts with peroxy acid and gives an epoxide.  Further, the epoxide undergoes an acid-catalyzed opening to form a trans diol.

(h)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

• Hydroboration-oxidation reaction: Addition of $\text{–H and –OH}$ group across the double bond in presence of borane and hydrogen peroxide with base is known as hydroboration-oxidation reaction.  It follows Anti-Markovnikov’s addition.

• Anti-Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the less substitution position of carbon-carbon double bond which provides alkyl halides.

  

(i)

Interpretation Introduction

Interpretation:

The product obtained for given reaction has to be predicted.

Concept Introduction:

Syn-dihydroxylation: In this reaction alkene reacts with osmium tetroxide and gives an osmate ester.  Further, the osmate ester treated with N-methylmorpholine N-oxide to form a cisdiol.