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Chapter 24: Problem 27

Write the condensed structural formulas for two alkenes and one alkyne that all have the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10}\) .

Short Answer

Expert verified
The two alkenes with the molecular formula C6H10 are 1-Butene: CH2=CH-CH2-CH2-CH3 and 2-Butene: CH3-CH=CH-CH2-CH3. The one alkyne is 1-Hexyne: CH鈮-CH2-CH2-CH2-CH3.

Step by step solution

01

Determine the Number of Double and Triple Bonds

For alkenes, we can use the degree of unsaturation formula to determine the number of double bonds: Degree of Unsaturation = \(\frac{(2 * N_{carbon} + 2 - N_{hydrogen})}{2}\) where N_carbon and N_hydrogen are the number of carbon and hydrogen atoms, respectively. Plugging in the values for C6H10, we get: Degree of Unsaturation = \(\frac{(2 * 6 + 2 - 10)}{2}\) = 2 The degree of unsaturation is 2, which means there will be a total of 2 double bonds or 1 triple bond.
02

Identify the Alkenes

There are two alkenes with the molecular formula C6H10, and both have a single carbon-carbon double bond. We will identify these two isomers by varying the position of the double bond: 1. The first alkene has the double bond between the first two carbons (1-Butene): CH2=CH-CH2-CH2-CH3 2. The second alkene has the double bond between the second and third carbons (2-Butene): CH3-CH=CH-CH2-CH3
03

Identify the Alkyne

There is only one alkyne with the molecular formula C6H10. The alkyne has a carbon-carbon triple bond. We will find it by varying the position of the triple bond: 1. The only viable alkyne has the triple bond between the first two carbons (1-Hexyne): CH鈮-CH2-CH2-CH2-CH3 In conclusion, the two alkenes with the molecular formula C6H10 are 1-Butene and 2-Butene, and the one alkyne is 1-Hexyne.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Alkenes
Alkenes are a group of hydrocarbons that contain at least one carbon-carbon double bond. These organic compounds are unsaturated, which means they have fewer hydrogen atoms than alkanes, their saturated counterparts. The general molecular formula for alkenes is \( C_nH_{2n} \), where \( n \) is the number of carbon atoms in the molecule.

For the molecule \( C_6H_{10} \), the presence of a double bond is established by its degree of unsaturation. When constructing alkenes with this formula, we strategically place the double bond in different locations to create various isomers. For instance, when the double bond is at the beginning of the carbon chain, it forms 1-Butene, while placing it between the second and third carbons forms 2-Butene. Each of these isomers has distinct physical and chemical properties, which are important in chemical reactions and synthesis.
Degree of Unsaturation
The degree of unsaturation is a vital concept in organic chemistry used to determine the amount of unsaturation within a molecule. It provides insights into the number of rings and pi bonds (double or triple bonds) a molecule possesses. Calculated using the formula \( \frac{{2 * N_{carbon} + 2 - N_{hydrogen}}}{{2}} \), the degree of unsaturation indicates the total number of pi bonds and rings in the molecule.

For example, the degree of unsaturation for a molecule with the formula \( C_6H_{10} \) is calculated to be 2, suggesting that the compound could have two double bonds, one double bond and one ring, or one triple bond. Knowledge of the degree of unsaturation helps us predict and deduce the structure of organic compounds, leading to an understanding of their chemical behavior and the reactions they may undergo.
Alkyne
Alkynes are hydrocarbons characterized by the presence of a carbon-carbon triple bond. They form a subset of unsaturated compounds and have the general formula \( C_nH_{2n-2} \). Alkynes are less common than alkenes but are known for their distinctive chemical reactions, such as the ability to undergo addition reactions where the triple bond opens up to add atoms across it.

In the case of \( C_6H_{10} \), one viable alkyne structure exists, called 1-Hexyne. This molecule features a triple bond at the first and second carbon atoms, creating a linear and more rigid structure compared to alkenes. Alkynes play an essential role in synthetic chemistry, particularly in the creation of new carbon-carbon bonds, because the triple bond can serve as a reactive site for many types of chemical transformations.

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Most popular questions from this chapter

Draw the three distinct geometric isomers of \(2,4\)-hexadiene.

(a) Draw the chemical structure of a generic amino acid, using \(R\) for the side chain. (b) When amino acids react to form proteins, do they do so via substitution, addition, or condensation reactions? (c) Draw the bond that links amino acids together in proteins. What is this called?

Indicate whether each statement is true or false. (a) Alkanes do not contain any carbon-carbon multiple bonds. (b) Cyclobutane contains a four-membered ring. (c) Alkenes contain carbon-carbon triple bonds. (d) Alkynes contain carbon-carbon double bonds. (e) Pentane is a saturated hydrocarbon but 1-pentene is an unsaturated hydrocarbon. (f) Cyclohexane is an aromatic hydrocarbon. (g) The methyl group contains one less hydrogen atom than methane.

A typical amino acid with one amino group and one carboxylic acid group, such as serine, can exist in water in several ionic forms. (a) Suggest the forms of the amino acid at low pH and at high pH. (b) Amino acids generally have two pK\(_{a}\) values, one in the range of 2 to 3 and the other in the range of 9 to \(10 .\) Serine, for example, has pK\(_{a}\) values of 2.19 and \(9.21 .\) Using species such as acetic acid and ammonia as models, suggest the origin of the two pK\(_{a}\) values. (c) Glutamic acid is an amino acid that has three \(\mathrm{p} K_{a}^{\prime} \mathrm{s} : 2.10,4.07,\) and \(9.47 .\) Draw the structure of glutamic acid, and assign each \(\mathrm{pK}_{a}\) to the appropriate part of the molecule. (d) An unknown amino acid is titrated with strong base, producing the following titration curve. Which amino acids are likely candidates for the unknown?

The molar heat of combustion of gaseous cyclopropane is \(-2089 \mathrm{kJ} / \mathrm{mol};\) that for gaseous cyclopentane is \(-3317 \mathrm{kJ} / \mathrm{mol} .\) Calculate the heat of combustion per \(\mathrm{CH}_{2}\) group in the two cases, and account for the difference.
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