Organic Chemistry - With Access (Custom)
Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
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Chapter 9.SE, Problem 42AP
Interpretation Introduction

a)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 42AP , additional homework tip  1

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH3 in liquid NH3. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

b)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 42AP , additional homework tip  2

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH3 in liquid NH3. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

c)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 42AP , additional homework tip  3

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH3 in liquid NH3. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H3 in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

d)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 42AP , additional homework tip  4

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH3 in liquid NH3. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H3SO4 in the presence of HgSO4 to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

e)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 42AP , additional homework tip  5

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH3 in liquid NH3. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

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Chapter 9 Solutions

Organic Chemistry - With Access (Custom)

Ch. 9.8 - Prob. 11PCh. 9.9 - Show the terminal alkyne and alkyl halide from...Ch. 9.9 - Beginning with acetylene and any alkyl halide...Ch. 9.SE - Name the following alkynes, and predict the...Ch. 9.SE - From what alkyne might each of the following...Ch. 9.SE - Prob. 16VCCh. 9.SE - The following cycloalkyne is too unstable to...Ch. 9.SE - Prob. 18MPCh. 9.SE - Assuming that strong acids add to alkynes in the...Ch. 9.SE - Prob. 20MPCh. 9.SE - Prob. 21MPCh. 9.SE - Prob. 22MPCh. 9.SE - Prob. 23MPCh. 9.SE - Prob. 24MPCh. 9.SE - Reaction of acetone with D3O+ yields...Ch. 9.SE - Give IUPAC names for the following compounds:Ch. 9.SE - Draw structures corresponding to the following...Ch. 9.SE - Prob. 28APCh. 9.SE - Prob. 29APCh. 9.SE - Prob. 30APCh. 9.SE - Predict the products from reaction of l-hexyne...Ch. 9.SE - Prob. 32APCh. 9.SE - Prob. 33APCh. 9.SE - Propose structures for hydrocarbons that give the...Ch. 9.SE - Identify the reagents a-c in the following scheme:Ch. 9.SE - Prob. 36APCh. 9.SE - Prob. 37APCh. 9.SE - Prob. 38APCh. 9.SE - How would you carry out the following...Ch. 9.SE - Prob. 40APCh. 9.SE - Synthesize the following compounds using 1-butyne...Ch. 9.SE - Prob. 42APCh. 9.SE - Prob. 43APCh. 9.SE - Prob. 44APCh. 9.SE - Prob. 45APCh. 9.SE - A hydrocarbon of unknown structure has the formula...Ch. 9.SE - Compound A(C9H12) absorbed 3 equivalents of H2 on...Ch. 9.SE - Hydrocarbon A has the formula C12H8. It absorbs 8...Ch. 9.SE - Occasionally, a chemist might need to invert the...Ch. 9.SE - Prob. 50APCh. 9.SE - Prob. 51APCh. 9.SE - Prob. 52APCh. 9.SE - Prob. 53APCh. 9.SE - Prob. 54APCh. 9.SE - Prob. 55APCh. 9.SE - Prob. 56APCh. 9.SE - Prob. 57AP
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