Organic Chemistry - With Access (Custom)
Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
Question
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Chapter 9.SE, Problem 37AP
Interpretation Introduction

a)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 37AP , additional homework tip  1

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H2SO4 in the presence of HgSO4 are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Interpretation Introduction

b)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 37AP , additional homework tip  2

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Interpretation Introduction

c)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 37AP , additional homework tip  3

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH2 in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Interpretation Introduction

d)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 37AP , additional homework tip  4

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H2 in the presence of Lindlar catalyst. The hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Interpretation Introduction

e)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 37AP , additional homework tip  5

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO4. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO2 also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Interpretation Introduction

f)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 37AP , additional homework tip  6

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

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Students have asked these similar questions
Are the products of the given reaction correct?  Why or why not?
The question below asks why the products shown are NOT the correct products.  I asked this already, and the person explained why those are the correct products, as opposed to what we would think should be the correct products.  That's the opposite of what the question was asking.  Why are they not the correct products? A reaction mechanism for how we arrive at the correct products is requested ("using key intermediates").  In other words, why is HCl added to the terminal alkene rather than the internal alkene?
My question is whether HI adds to both double bonds, and if it doesn't, why not?

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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