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Chain with double bond or triple bond

“Tie-breaker” rules for IUPAC nomenclature of organic compoundsShould double or triple bonds have preference for low locants in IUPAC nomenclature?Bond length comparison between two carbon atomsWhy can two carbon atoms not form more than triple bond with each other?Deciding higher priority order between a triple bond and tertiary carbonSelection of parent chain (IUPAC nomenclature)

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2

$begingroup$

In this hydrocarbon there can be two main chains: one with two double bonds and one with a double and a triple bond

Both main chains contain seven carbon atoms.
Which will be considered correct and why?

organic-chemistry nomenclature hydrocarbons

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edited Oct 2 at 20:28

andselisk♦

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asked Oct 2 at 9:08

SatwikSatwik

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5

2

$begingroup$

In this hydrocarbon there can be two main chains: one with two double bonds and one with a double and a triple bond

Both main chains contain seven carbon atoms.
Which will be considered correct and why?

organic-chemistry nomenclature hydrocarbons

share|improve this question

edited Oct 2 at 20:28

andselisk♦

26.1k88 gold badges8282 silver badges157157 bronze badges

asked Oct 2 at 9:08

SatwikSatwik

10544 bronze badges

$endgroup$

add a comment
 | 

$begingroup$

In this hydrocarbon there can be two main chains: one with two double bonds and one with a double and a triple bond

Both main chains contain seven carbon atoms.
Which will be considered correct and why?

organic-chemistry nomenclature hydrocarbons

share|improve this question

edited Oct 2 at 20:28

andselisk♦

26.1k88 gold badges8282 silver badges157157 bronze badges

asked Oct 2 at 9:08

SatwikSatwik

10544 bronze badges

$endgroup$

share|improve this question

edited Oct 2 at 20:28

andselisk♦

26.1k88 gold badges8282 silver badges157157 bronze badges

asked Oct 2 at 9:08

SatwikSatwik

10544 bronze badges

share|improve this question

edited Oct 2 at 20:28

andselisk♦

26.1k88 gold badges8282 silver badges157157 bronze badges

asked Oct 2 at 9:08

SatwikSatwik

10544 bronze badges

edited Oct 2 at 20:28

andselisk♦

26.1k88 gold badges8282 silver badges157157 bronze badges

edited Oct 2 at 20:28

andselisk♦

26.1k88 gold badges8282 silver badges157157 bronze badges

asked Oct 2 at 9:08

SatwikSatwik

10544 bronze badges

asked Oct 2 at 9:08

SatwikSatwik

10544 bronze badges

1 Answer
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According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), as already mentioned in the question, the first relevant criterion to be considered in choosing a principal chain is the length of the chain.

When there is a choice for the principal chain, the following criteria are applied, in the order listed, until a decision is reached:

P-44.4.1 If the criteria of P-44.1 through P-44.3, where applicable, do not effect a choice of a senior parent structure, the following criteria are applied successively until there are no alternatives remaining. (…)

The senior ring, ring system, or principal chain:

(a) has the greater number of multiple bonds (P-44.4.1.1);

(b) has the greater number of double bonds (P-44.4.1.2);

(…)

(h) has the lower locant for an attached group expressed as a suffix (P-44.4.1.8);

(…)

Since both possible chains in this case have two multiple bonds, Rule (a) is not enough to make a choice.

According to Rule (b), the principal chain is the hepta-1,6-diene because it has the greater number of double bonds.

Therefore, the preferred IUPAC name (PIN) is 4-(prop-2-yn-1-yl)hepta-1,6-diene.

share|improve this answer

answered Oct 2 at 16:28

Loong♦Loong

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8

$begingroup$

According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), as already mentioned in the question, the first relevant criterion to be considered in choosing a principal chain is the length of the chain.

When there is a choice for the principal chain, the following criteria are applied, in the order listed, until a decision is reached:

P-44.4.1 If the criteria of P-44.1 through P-44.3, where applicable, do not effect a choice of a senior parent structure, the following criteria are applied successively until there are no alternatives remaining. (…)

The senior ring, ring system, or principal chain:

(a) has the greater number of multiple bonds (P-44.4.1.1);

(b) has the greater number of double bonds (P-44.4.1.2);

(…)

(h) has the lower locant for an attached group expressed as a suffix (P-44.4.1.8);

(…)

Since both possible chains in this case have two multiple bonds, Rule (a) is not enough to make a choice.

According to Rule (b), the principal chain is the hepta-1,6-diene because it has the greater number of double bonds.

Therefore, the preferred IUPAC name (PIN) is 4-(prop-2-yn-1-yl)hepta-1,6-diene.

share|improve this answer

answered Oct 2 at 16:28

Loong♦Loong

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$endgroup$

add a comment
 | 

8

$begingroup$

According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), as already mentioned in the question, the first relevant criterion to be considered in choosing a principal chain is the length of the chain.

When there is a choice for the principal chain, the following criteria are applied, in the order listed, until a decision is reached:

P-44.4.1 If the criteria of P-44.1 through P-44.3, where applicable, do not effect a choice of a senior parent structure, the following criteria are applied successively until there are no alternatives remaining. (…)

The senior ring, ring system, or principal chain:

(a) has the greater number of multiple bonds (P-44.4.1.1);

(b) has the greater number of double bonds (P-44.4.1.2);

(…)

(h) has the lower locant for an attached group expressed as a suffix (P-44.4.1.8);

(…)

Since both possible chains in this case have two multiple bonds, Rule (a) is not enough to make a choice.

According to Rule (b), the principal chain is the hepta-1,6-diene because it has the greater number of double bonds.

Therefore, the preferred IUPAC name (PIN) is 4-(prop-2-yn-1-yl)hepta-1,6-diene.

share|improve this answer

answered Oct 2 at 16:28

Loong♦Loong

38.2k99 gold badges9393 silver badges200200 bronze badges

$endgroup$

add a comment
 | 

$begingroup$

According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), as already mentioned in the question, the first relevant criterion to be considered in choosing a principal chain is the length of the chain.

When there is a choice for the principal chain, the following criteria are applied, in the order listed, until a decision is reached:

P-44.4.1 If the criteria of P-44.1 through P-44.3, where applicable, do not effect a choice of a senior parent structure, the following criteria are applied successively until there are no alternatives remaining. (…)

The senior ring, ring system, or principal chain:

(a) has the greater number of multiple bonds (P-44.4.1.1);

(b) has the greater number of double bonds (P-44.4.1.2);

(…)

(h) has the lower locant for an attached group expressed as a suffix (P-44.4.1.8);

(…)

Since both possible chains in this case have two multiple bonds, Rule (a) is not enough to make a choice.

According to Rule (b), the principal chain is the hepta-1,6-diene because it has the greater number of double bonds.

Therefore, the preferred IUPAC name (PIN) is 4-(prop-2-yn-1-yl)hepta-1,6-diene.

share|improve this answer

answered Oct 2 at 16:28

Loong♦Loong

38.2k99 gold badges9393 silver badges200200 bronze badges

$endgroup$

share|improve this answer

answered Oct 2 at 16:28

Loong♦Loong

38.2k99 gold badges9393 silver badges200200 bronze badges

answered Oct 2 at 16:28

Loong♦Loong

38.2k99 gold badges9393 silver badges200200 bronze badges

answered Oct 2 at 16:28

Loong♦Loong

38.2k99 gold badges9393 silver badges200200 bronze badges