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Distinguish between isomerism and resonance. Distinguish between structural and geometric isomerism. When writing the various structural isomers, the most difficult task is identifying which are different isomers and which are identical to a previously written structure — that is, which are compounds that differ only by the rotation of a carbon single bond. How do you distinguish between structural isomers and those that are identical? Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C 4 H 8 . Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one or more bonds in the compound, so both can exhibit cis- trans isomerism. What is required for an alkene or cycloalkane to exhibit cis-trans isomerism? Explain the difference between cis and trans isomers. Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table 21-4 can be structural isomers of carboxylic acids? What is optical isomerism? What do you look for to determine whether an organic compound exhibits optical isomerism? 1-Bromo-1-chloroethane is optically active whereas 1-bromo-2-chloroethane is not optically active. Explain.

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Chemistry: An Atoms First Approach

2nd Edition
Steven S. Zumdahl + 1 other
Publisher: Cengage Learning
ISBN: 9781305079243

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BuyFindarrow_forward

Chemistry: An Atoms First Approach

2nd Edition
Steven S. Zumdahl + 1 other
Publisher: Cengage Learning
ISBN: 9781305079243
Chapter 21, Problem 6RQ
Textbook Problem
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Distinguish between isomerism and resonance. Distinguish between structural and geometric isomerism. When writing the various structural isomers, the most difficult task is identifying which are different isomers and which are identical to a previously written structurethat is, which are compounds that differ only by the rotation of a carbon single bond. How do you distinguish between structural isomers and those that are identical?

Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C4H8. Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one or more bonds in the compound, so both can exhibit cis- trans isomerism. What is required for an alkene or cycloalkane to exhibit cis-trans isomerism? Explain the difference between cis and trans isomers.

Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table 21-4 can be structural isomers of carboxylic acids?

What is optical isomerism? What do you look for to determine whether an organic compound exhibits optical isomerism? 1-Bromo-1-chloroethane is optically active whereas 1-bromo-2-chloroethane is not optically active. Explain.

Interpretation Introduction

Interpretation: The given questions based upon isomerism and functional groups are to be answered.

Concept introduction: A functional group is a group of elements that changes the physical as well as chemical properties of a compound. They play a significant role in naming and reactivity of a chemical reaction. Some of the common examples of functional groups are alcohol, carboxylic acid, amine, aldehyde, ketone and many others.

Explanation of Solution

Explanation

To determine: Answers of several questions based upon isomerism and functional groups.

Isomerism involves different arrangements of atoms in a molecule while resonance involves different arrangement of electrons.

In resonance, the arrangement of atoms in a molecule is same but there is movement of electrons around the molecule. It can be represented by resonance structures. When compounds have the same atoms but their arrangement is different, then it is known as isomerism.

Geometric isomerism is a type of stereoisomerism. It is a result of restricted rotation within a molecule while structural isomerism occurs due to difference in the arrangement of atoms within the molecules without any reference to space.

Since structural isomers are the compounds having same molecular formula but different structural formulas, they can be distinguished by the position and functional group.

Alkenes and cycloalkanes are structural isomers of each other. Examples are butene and cyclobutane. Both have same molecular formulas but their structures are different.

Figure 1

Figure 2

When similar groups are attached on same side of the double bond, then it is cis isomer and when they are on the opposite side they are called trans isomers.

For a molecule to exhibit cis trans isomerism, two atoms or groups attached to one end of the double bond should be different. When similar groups are adjacent to each other, it is cis-isomer and when similar groups are opposite to each other, it is called trans-isomer. Alkenes and cycloalkanes both have restricted rotation about one or more bonds in the compound, so that they can exhibit cis-trans isomerism.

Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones...

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Chapter 21 Solutions

Chemistry: An Atoms First Approach
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Ch. 21 - What are carbohydrates, and what are the monomers...Ch. 21 - Describe the structural differences between DNA...Ch. 21 - A confused student was doing an isomer problem and...Ch. 21 - For the following formulas, what types of...Ch. 21 - What is wrong with the following names? Give the...Ch. 21 - The following organic compounds cannot exist. Why?...Ch. 21 - If you had a group of hydrocarbons, what...Ch. 21 - Which of the functional groups in Table 21-4 can...Ch. 21 - A polypeptide is also called a polyamide. Nylon is...Ch. 21 - Give an example reaction that would yield the...Ch. 21 - Give an example reaction that would yield the...Ch. 21 - What is polystyrene? The following processes...Ch. 21 - Answer the following questions regarding the...Ch. 21 - In Section 21-6, three important classes of...Ch. 21 - Draw the five structural isomers of hexane...Ch. 21 - Name the structural isomers in Exercise 13.Ch. 21 - Draw all the structural isomers for C8H18 that...Ch. 21 - Draw all the structural isomers for C8H18 that...Ch. 21 - Draw a structural formula for each of the...Ch. 21 - Draw a structural formula for each of the...Ch. 21 - Draw the structural formula for each of the...Ch. 21 - Draw the structure for...Ch. 21 - Name each of the following. a. b. c. d.Ch. 21 - Name each of the following cyclic alkanes, and...Ch. 21 - Give two examples of saturated hydrocarbons. How...Ch. 21 - Draw the structures for two examples of...Ch. 21 - Name each of the following alkenes. a. CH2 = CH ...Ch. 21 - Name each of the following alkenes or alkynes. a....Ch. 21 - Give the structure for each of the following. a....Ch. 21 - Give the structure for each of the following. a....Ch. 21 - Give the structure of each of the following...Ch. 21 - Cumene is the starting material for the industrial...Ch. 21 - Name each of the following. a. b. CH3CH2CH2CCl3 c....Ch. 21 - Name each of the following compounds. a. b. c. d....Ch. 21 - There is only one compound that is named...Ch. 21 - Consider the following four structures. a. Which...Ch. 21 - Which of the compounds in Exercises 25 and 27...Ch. 21 - Which of the compounds in Exercises 26 and 28...Ch. 21 - Draw all the structural isomers of C5H10. Ignore...Ch. 21 - Which of the structural isomers in Exercise 37...Ch. 21 - Draw all the structural and geometrical (cistrans)...Ch. 21 - Draw all the structural and geometrical (cistrans)...Ch. 21 - Draw all structural and geometrical (cistrans)...Ch. 21 - Cistrans isomerism is also possible in molecules...Ch. 21 - Draw the following. a. cis-2-hexene b....Ch. 21 - Name the following compounds. a. b. c.Ch. 21 - If one hydrogen in a hydrocarbon is replaced by a...Ch. 21 - There are three isomers of dichlorobenzene, one of...Ch. 21 - Identify each of the following compounds as a...Ch. 21 - Identify the functional groups present in the...Ch. 21 - Mimosine is a natural product found in large...Ch. 21 - Minoxidil (C9H15N5O) is a compound produced by...Ch. 21 - For each of the following alcohols, give the...Ch. 21 - Draw structural formulas for each of the following...Ch. 21 - Name all the alcohols that have the formula...Ch. 21 - Name all the aldehydes and ketones that have the...Ch. 21 - Name the following compounds. a. b. c.Ch. 21 - Draw the structural formula for each of the...Ch. 21 - Name the following compounds. a. b. c. HCOOHCh. 21 - Draw a structural formula for each of the...Ch. 21 - Which of the following statements is(are) false?...Ch. 21 - Draw the isomer(s) specified. There may be more...Ch. 21 - Complete the following reactions. a. b. c. d.Ch. 21 - Reagents such as HCl, HBr, and HOH (H2O) can add...Ch. 21 - When toluene (C6H5CH3) reacts with chlorine gas in...Ch. 21 - Why is it preferable to produce chloroethane by...Ch. 21 - Using appropriate reactants, alcohols can be...Ch. 21 - Oxidation of an aldehyde yields a carboxylic acid:...Ch. 21 - How would you synthesize each of the following? a....Ch. 21 - What tests could you perform to distinguish...Ch. 21 - How would you synthesize the following esters? a....Ch. 21 - Complete the following reactions. a. CH3CO2H +...Ch. 21 - Kel-F is a polymer with the structure What is the...Ch. 21 - What monomer(s) must be used to produce the...Ch. 21 - Super glue contains methyl cyanoacrylate, which...Ch. 21 - Isoprene is the repeating unit in natural rubber....Ch. 21 - Kevlar, used in bulletproof vests, is made by the...Ch. 21 - The polyester formed from lactic acid, is used for...Ch. 21 - Polyimides are polymers that are tough and stable...Ch. 21 - The Amoco Chemical Company has successfully raced...Ch. 21 - Polystyrene can be made more rigid by...Ch. 21 - Polyesters containing double bonds are often...Ch. 21 - Which of the following polymers would be stronger...Ch. 21 - Poly(lauryl methacrylate) is used as an additive...Ch. 21 - Which of the amino acids in Fig. 21-18 contain the...Ch. 21 - When pure crystalline amino acids are heated,...Ch. 21 - Aspartame, the artificial sweetener marketed under...Ch. 21 - Glutathione, a tripeptide found in virtually all...Ch. 21 - Draw the structures of the two dipeptides that can...Ch. 21 - Draw the structures of the tripeptides glyalaser...Ch. 21 - Write the sequence of all possible tetrapeptides...Ch. 21 - How many different pentapeptides can be formed...Ch. 21 - Give an example of amino acids that could give...Ch. 21 - What types of interactions can occur between the...Ch. 21 - Oxygen is carried from the lungs to tissues by the...Ch. 21 - Over 100 different kinds of mutant hemoglobin...Ch. 21 - Draw cyclic structures for D-ribose and D-mannose.Ch. 21 - Indicate the chiral carbon atoms found in the...Ch. 21 - In addition to using numerical prefixes in the...Ch. 21 - Glucose can occur in three forms: two cyclic forms...Ch. 21 - What are the structural differences between - and...Ch. 21 - Cows can digest cellulose, but humans cant. Why...Ch. 21 - Which of the amino acids in Fig. 21-18 contain...Ch. 21 - Why is glycine not optically active?Ch. 21 - Which of the noncyclic isomers of...Ch. 21 - How many chiral carbon atoms does the following...Ch. 21 - Part of a certain DNA sequence is GGTCTATAC. What...Ch. 21 - The codons (words) in DNA (that specify which...Ch. 21 - Which base will hydrogen-bond with uracil within...Ch. 21 - Tautomers are molecules that differ in the...Ch. 21 - The base sequences in mRNA that code for certain...Ch. 21 - The change of a single base in the DNA sequence...Ch. 21 - Draw the following incorrectly named compounds and...Ch. 21 - In the presence of light, chlorine can substitute...Ch. 21 - Polychlorinated dibenzo-p-dioxins (PCDDs) are...Ch. 21 - Consider the following five compounds. a....Ch. 21 - The two isomers having the formula C2H6O boil at...Ch. 21 - Ignoring ring compounds, which isomer of C2H4O2...Ch. 21 - Explain why methyl alcohol is soluble in water in...Ch. 21 - Is octanoic acid more soluble in 1 M HCl, 1 M...Ch. 21 - Consider the compounds butanoic acid, pentanal,...Ch. 21 - A compound containing only carbon and hydrogen is...Ch. 21 - Three different organic compounds have the formula...Ch. 21 - Consider the following polymer: Is this polymer a...Ch. 21 - Nylon is named according to the number of C atoms...Ch. 21 - The polymer nitrile is a copolymer made from...Ch. 21 - Polyaramid is a term applied to polyamides...Ch. 21 - When acrylic polymers are burned, toxic fumes are...Ch. 21 - Ethylene oxide, is an important industrial...Ch. 21 - Another way of producing highly crosslinked...Ch. 21 - Monosodium glutamate (MSG) is commonly used as a...Ch. 21 - a. Use bond energies (see Table 3-3) to estimate H...Ch. 21 - The reaction to form a phosphate-ester linkage...Ch. 21 - Considering your answers to Exercises 130 and 131,...Ch. 21 - All amino acids have at least two functional...Ch. 21 - The average molar mass of one base pair of...Ch. 21 - When heat is added to proteins, the hydrogen...Ch. 21 - In glycine, the carboxylic acid group has Ka = 4.3...Ch. 21 - Name each of the following alkanes. a....Ch. 21 - Name each of the following alkanes. a. b. c.Ch. 21 - Name each of the following cyclic alkanes. a. b....Ch. 21 - Name each of the following alkenes and alkynes. a....Ch. 21 - a. Name each of the following alcohols. b. Name...Ch. 21 - Name each of the following organic compounds. a....Ch. 21 - Esterification reactions are carried out in the...Ch. 21 - Rank these organic compound in terms of increasing...Ch. 21 - The isoelectric point of an amino acid is the pH...Ch. 21 - In 1994 chemists at Texas A M University reported...Ch. 21 - The structure of tartaric acid is a. Is the form...Ch. 21 - Consider a sample of a hydrocarbon at 0.959 atm...Ch. 21 - Mycomycin, a naturally occurring antibiotic...Ch. 21 - Sorbic acid is used to prevent mold and fungus...Ch. 21 - Consider the following reactions. For parts b-d,...Ch. 21 - Polycarbonates are a class of thermoplastic...Ch. 21 - A urethane linkage occurs when an alcohol adds...Ch. 21 - ABS plastic is a tough, hard plastic used in...Ch. 21 - Stretch a rubber band while holding it gently to...Ch. 21 - Alcohols are very useful starting materials for...Ch. 21 - A chemical breathalyzer test works because ethanol...Ch. 21 - Estradiol is a female hormone with the following...Ch. 21 - An organometallic compound is one containing at...Ch. 21 - Helicenes are extended fused polyaromatic...Ch. 21 - For each of the following, fill in the blank with...Ch. 21 - Choose one of the following terms to match the...

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