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Chapter 22: Problem 150

Sorbic acid is used to prevent mold and fungus growth in some food products, especially cheeses. The systematic name for sorbic acid is 2,4-hexadienoic acid. Draw structures for the four geometrical isomers of sorbic acid.

Short Answer

Expert verified
The four geometrical isomers of sorbic acid (2,4-hexadienoic acid) are: 1. cis,cis-isomer: Hydrogen atoms are in the cis configuration on both double bonds, and the carboxyl group is also on the same side as the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] 2. cis,trans-isomer: Hydrogen atoms are in the cis configuration on the first double bond and in the trans configuration on the second double bond, with the carboxyl group on the opposite side of the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] 3. trans,cis-isomer: Hydrogen atoms are in the trans configuration on the first double bond and in the cis configuration on the second double bond, with the carboxyl group on the same side as the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] 4. trans,trans-isomer: Hydrogen atoms are in the trans configuration on both double bonds, and the carboxyl group is also on the opposite side of the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\]

Step by step solution

01

Write the main carbon chain of 2,4-hexadienoic acid

First, we need to write the main carbon chain of 2,4-hexadienoic acid. This compound has a six-carbon chain, with a carboxyl group (-COOH) attached to the first carbon. It has two double bonds at carbon positions 2 and 4. The rest of the carbons will have hydrogen atoms attached to them.
02

Identify positions of double bonds along the main chain

The double bonds are present at the second and fourth carbon positions. In drawing geometrical isomers, we will be focusing on the arrangement of groups around these double bonds.
03

Determine possible geometrical isomers

We will now take the main carbon chain with the double bonds and arrange the hydrogen atoms and the carboxyl group in different positions across the double bonds to form the four geometrical isomers. To do this, we'll consider the following options for each double bond: - The hydrogen atoms on the same side of the double bond (cis configuration) - The hydrogen atoms on opposite sides of the double bond (trans configuration) Here are the four geometrical isomers for 2,4-hexadienoic acid (sorbic acid): 1. cis,cis-isomer: Hydrogen atoms are in the cis configuration on both double bonds. The carboxyl group is also on the same side as the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] 2. cis,trans-isomer: Hydrogen atoms are in the cis configuration on the first double bond and in the trans configuration on the second double bond. The carboxyl group is on the opposite side of the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] 3. trans,cis-isomer: Hydrogen atoms are in the trans configuration on the first double bond and in the cis configuration on the second double bond. The carboxyl group is on the same side as the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] 4. trans,trans-isomer: Hydrogen atoms are in the trans configuration on both double bonds. The carboxyl group is also on the opposite side of the hydrogen atom on the second double bond. \[CH_3-CH=CH-CH=CH-COOH\] These are the four geometrical isomers of 2,4-hexadienoic acid (sorbic acid).

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Key Concepts

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

Sorbic Acid
Sorbic acid is a naturally occurring compound widely used as a food preservative to inhibit the growth of mold, yeast, and fungi. It's most commonly found in products like cheese, baked goods, and beverages. This makes sorbic acid a pivotal component in the food industry, ensuring longevity and safety in your favorite food items.
The structure of sorbic acid consists of a six-carbon atom chain, which places it among larger organic acids beneficial for industrial use.
Key attributes include:
  • A carboxyl group (-COOH) attached to the first carbon atom.
  • Two double bonds, enhancing its chemical reactivity and usefulness.
Understanding sorbic acid鈥檚 structure is crucial for appreciating how it functions as a preservative in everyday foods.
2,4-Hexadienoic Acid
Scientifically known as 2,4-hexadienoic acid, this compound is the same as sorbic acid but refers to its systematic name based on IUPAC naming conventions. This name gives insight into its molecular structure and the specific arrangement of its atoms.
This systematic naming breaks down as follows:
  • The 'hex-' prefix indicates six carbon atoms in the main chain.
  • 'diene' specifies two double bonds within the chain.
  • Numbers '2,4' indicate the positions of these double bonds, which are between the second and third, and fourth and fifth carbon atoms respectively.
Such detailed naming helps chemists and students easily deduce the structure and characteristics of organic compounds. Recognizing the positions of double bonds is especially important when examining isomerism, which can dramatically impact a compound's properties.
Cis-Trans Isomerism
Cis-trans isomerism is a form of stereoisomerism where isomers have the same molecular formula but differ in the spatial arrangement of atoms around a double bond. This type of isomerism is critical in the study of organic compounds, particularly those like 2,4-hexadienoic acid.
  • In 'cis' isomers, similar groups or atoms are on the same side of the double bond.
  • In 'trans' isomers, they are on opposite sides.
For sorbic acid (or 2,4-hexadienoic acid), these arrangements around its two double bonds create four possible isomers: cis,cis; cis,trans; trans,cis; and trans,trans. Each configuration can affect how the molecule interacts with other substances, influencing its melting point, solubility, and even biological activity.
Understanding these isomers helps in predicting the behavior of organic molecules, a vital ability for fields ranging from pharmaceuticals to material science.

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Most popular questions from this chapter

For each of the following, fill in the blank with the correct response(s). All of the following pertain to nucleic acids. a. The substance in the nucleus of the cell that stores and transmits genetic information is DNA, which stands for _______. b. The basic repeating monomer units of DNA and RNA are called ________. c. The pentose deoxyribose is found in DNA, whereas _______ is found in RNA. d. The basic linkage in DNA or RNA between the sugar molecule and phosphoric acid is a phosphate ______ linkage. e. The bases on opposite strands of DNA are said to be _______ to each other, which means the bases fit together specifically by hydrogen bonding to one another. f. In a strand of normal DNA, the base _______ is always found paired with the base adenine, whereas ______ is always found paired with cytosine. g. A given segment of the DNA molecule, which contains the molecular coding for a specific protein to be synthesized, is referred to as a __________. h. During protein synthesis,_________ RNA molecules attach to and transport specific amino acids to the appropriate position on the pattern provided by_________ RNA molecules. i. The codes specified by _______ are responsible for assembling the correct primary structure of proteins.

Three different organic compounds have the formula \(\mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}\). Only two of these isomers react with \(\mathrm{KMnO}_{4}\) (a strong oxidizing agent). What are the names of the products when these isomers react with excess \(\mathrm{KMnO}_{4} ?\)

If one hydrogen in a hydrocarbon is replaced by a halogen atom, the number of isomers that exist for the substituted compound depends on the number of types of hydrogen in the original hydrocarbon. Thus there is only one form of chloroethane (all hydrogens in ethane are equivalent), but there are two isomers of propane that arise from the substitution of a methyl hydrogen or a methylene hydrogen. How many isomers can be obtained when one hydrogen in each of the compounds named below is replaced by a chlorine atom? a. \(n\) -pentane c. 2,4 -dimethylpentane b. 2 -methylbutane d. methylcyclobutane

Consider the compounds butanoic acid, pentanal, \(n\) -hexane, and 1 -pentanol. The boiling points of these compounds (in no specific order) are \(69^{\circ} \mathrm{C}, 103^{\circ} \mathrm{C}, 137^{\circ} \mathrm{C}\), and \(164^{\circ} \mathrm{C}\). Match the boiling points to the correct compound.

There are three isomers of dichlorobenzene, one of which has now replaced naphthalene as the main constituent of mothballs. a. Identify the ortho, the meta, and the para isomers of dichlorobenzene. b. Predict the number of isomers for trichlorobenzene. c. It turns out that the presence of one chlorine atom on a benzene ring will cause the next substituent to add ortho or para to the first chlorine atom on the benzene ring. What does this tell you about the synthesis of \(m\) -dichlorobenzene? d. Which of the isomers of trichlorobenzene will be the hardest to prepare?
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