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Chapter 21

Organic Chemistry

Educators


Problem 1

What kinds of molecules often trigger our sense of smell?

Ly T.
Numerade Educator

Problem 2

What is organic chemistry?

Keenan M.
University of Miami

Problem 3

What is unique about carbon and carbon-based compounds? Why did life evolve around carbon?

Ly T.
Numerade Educator

Problem 4

Why does carbon form such a large diversity of compounds?

Keenan M.
University of Miami

Problem 5

Why does silicon exhibit less diversity of compounds than carbon does?

Ly T.
Numerade Educator

Problem 6

Describe the geometry and hybridization about a carbon atom that forms the following:
a. four single bonds.
b. two single bonds and one double bond.
c. one single bond and one triple bond.

Keenan M.
University of Miami

Problem 7

What are hydrocarbons? What are their main uses?

Ly T.
Numerade Educator

Problem 8

What are the main classifications of hydrocarbons? What are their generic molecular formulas?

Keenan M.
University of Miami

Problem 9

Explain the differences between a structural formula, a condensed structural formula, a carbon skeleton formula, a ball-and-stick model, and a space-filling model.

Ly T.
Numerade Educator

Problem 10

What are structural isomers? How do the properties of structural isomers differ from one another?

Keenan M.
University of Miami

Problem 11

What are optical isomers? How do the properties of optical isomers differ from one another?

Ly T.
Numerade Educator

Problem 12

Define each term related to optical isomerism: enantiomers, chiral, dextrorotatory, levorotatory, racemic mixture.

Keenan M.
University of Miami

Problem 13

What is the difference between saturated and unsaturated hydrocarbons?

Ly T.
Numerade Educator

Problem 14

What are the key differences in the way that alkanes, alkenes, and alkynes are named?

Keenan M.
University of Miami

Problem 15

Explain geometric isomerism in alkenes. How do the properties of geometric isomers differ from one another?

Ly T.
Numerade Educator

Problem 16

Describe and provide an example of a hydrocarbon combustion reaction.

Keenan M.
University of Miami

Problem 17

What kinds of reactions are common to alkanes? List an example of each.

Ly T.
Numerade Educator

Problem 18

Describe each kind of reaction.
a. substitution reaction
b. addition reaction
c. elimination reaction

Keenan M.
University of Miami

Problem 19

What kinds of reactions are common to alkenes? List an example of each.

Ly T.
Numerade Educator

Problem 20

Explain Markovnikov's rule and give an example of a reaction to which it applies.

Keenan M.
University of Miami

Problem 21

What is the structure of benzene? What are the different ways in which this structure is represented?

Ly T.
Numerade Educator

Problem 22

What kinds of reactions are common to aromatic compounds? Provide an example of each.

Keenan M.
University of Miami

Problem 23

What is a functional group? List some examples.

Ly T.
Numerade Educator

Problem 24

What is the generic structure of alcohols? Write the structures of two specific alcohols.

Keenan M.
University of Miami

Problem 25

Explain oxidation and reduction with respect to organic compounds.

Ly T.
Numerade Educator

Problem 26

Which kinds of reactions are common to alcohols? Provide an example of each.

Keenan M.
University of Miami

Problem 27

What are the generic structures for aldehydes and ketones? Write a structure for a specific aldehyde and ketone.

Ly T.
Numerade Educator

Problem 28

Which kinds of reactions are common to aldehydes and ketones? List an example of each.

Keenan M.
University of Miami

Problem 29

What are the generic structures for carboxylic acids and esters? Write a structure for a specific carboxylic acid and ester.

Ly T.
Numerade Educator

Problem 30

Which kinds of reactions are common to carboxylic acids and esters? Provide an example of each.

Keenan M.
University of Miami

Problem 31

What is the generic structure of ethers? Write the structures of two specific ethers.

Ly T.
Numerade Educator

Problem 32

What is the generic structure of amines? Write the structures of two specific amines.

Keenan M.
University of Miami

Problem 33

Based on the molecular formula, determine whether each compound is an alkane, alkene, or alkyne. (Assume that the hydrocarbons are noncyclic and there is no more than one multiple bond.)
a. C5H12
b. C3H6
c. C7H12
d. C11H22

Ronald P.
Numerade Educator

Problem 34

Based on the molecular formula, determine whether each compound is an alkane, alkene, or alkyne. (Assume that the hydrocarbons are noncyclic and there is no more than one multiple bond.)
a. C8H16
b. C4H6
c. C7H16
d. C2H2

Keenan M.
University of Miami

Problem 35

Write structural formulas for each of the nine structural isomers of heptane.

Ly T.
Numerade Educator

Problem 36

Write structural formulas for any 6 of the 18 structural isomers of octane.

Keenan M.
University of Miami

Problem 37

Determine whether each compound exhibits optical isomerism.

Ly T.
Numerade Educator

Problem 38

Determine whether each compound exhibits optical isomerism.

Keenan M.
University of Miami

Problem 39

Determine whether the molecules in each pair are the same or enantiomers.

Ly T.
Numerade Educator

Problem 40

Determine whether the molecules in each pair are the same or enantiomers.

Keenan M.
University of Miami

Problem 41

Name each alkane.

Ly T.
Numerade Educator

Problem 42

Name each alkane.

Keenan M.
University of Miami

Problem 43

Draw a structure for each alkane.
a. 3-ethylhexane
b. 3-ethyl-3-methylpentane
c. 2,3-dimethylbutane
d. 4,7-diethyl-2,2-dimethylnonane

Ly T.
Numerade Educator

Problem 44

Draw a structure for each alkane.
a. 2,2-dimethylpentane
b. 3-isopropylheptane
c. 4-ethyl-2,2-dimethylhexane
d. 4,4-diethyloctane

Keenan M.
University of Miami

Problem 45

Complete and balance each hydrocarbon combustion reaction.
a. CH3CH2CH3 + O2
b. CH3CH2CH"CH2 + O2
c. CH,CH + O2

Ly T.
Numerade Educator

Problem 46

Complete and balance each hydrocarbon combustion reaction.
a. CH3CH2CH2CH3 + O2
b. CH2"CHCH3 + O2
c. CH,CCH2CH3 + O2

Keenan M.
University of Miami

Problem 47

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.)

Ly T.
Numerade Educator

Problem 48

List all the possible products for each alkane substitution reaction. (Assume monosubstitution.)
a. CH4 + Cl2
b. CH3CH2Br + Br2
c. CH3CH2CH2CH3 + Cl2
d. CH3CHBr2 + Br2

Keenan M.
University of Miami

Problem 49

Write structural formulas for each of the possible isomers of n-hexene that are formed by moving the position of the double bond.

Ly T.
Numerade Educator

Problem 50

Write structural formulas for each of the possible isomers of n-pentyne that are formed by moving the position of the triple bond.

Keenan M.
University of Miami

Problem 51

Name each alkene.

Ly T.
Numerade Educator

Problem 52

Name each alkene.

Keenan M.
University of Miami

Problem 53

Name each alkyne.

Ly T.
Numerade Educator

Problem 54

Name each alkyne.

Keenan M.
University of Miami

Problem 55

Draw the correct structure for each compound.
a. 4-octyne
b. 3-nonene
c. 3,3-dimethyl-1-pentyne
d. 5-ethyl-3,6-dimethyl-2-heptene

Ly T.
Numerade Educator

Problem 56

Draw the correct structure for each compound.
a. 2-hexene
b. 1-heptyne
c. 4,4-dimethyl-2-hexene
d. 3-ethyl-4-methyl-2-pentene

Keenan M.
University of Miami

Problem 57

List the products of each alkene addition reaction

Ly T.
Numerade Educator

Problem 58

What are the products of each alkene addition reaction?

Keenan M.
University of Miami

Problem 59

Complete each hydrogenation reaction.

Ly T.
Numerade Educator

Problem 60

Complete each hydrogenation reaction.

Keenan M.
University of Miami

Problem 61

Name each monosubstituted benzene.

Ly T.
Numerade Educator

Problem 62

Name each monosubstituted benzene.

Keenan M.
University of Miami

Problem 63

Name each compound in which the benzene ring is best treated as a substituent.

Ly T.
Numerade Educator

Problem 64

Name each compound in which the benzene ring is best treated as a substituent.

Keenan M.
University of Miami

Problem 65

Name each disubstituted benzene.

Ly T.
Numerade Educator

Problem 66

Name each disubstituted benzene.

Keenan M.
University of Miami

Problem 67

Draw the structure for each compound.
a. isopropylbenzene
b. meta-dibromobenzene
c. 1-chloro-4-methylbenzene

Ly T.
Numerade Educator

Problem 68

Draw the structure for each compound.
a. ethylbenzene
b. 1-iodo-2-methylbenzene
c. para-diethylbenzene

Keenan M.
University of Miami

Problem 69

What are the products of each aromatic substitution reaction?

Ly T.
Numerade Educator

Problem 70

What are the products of each aromatic substitution reaction?

Keenan M.
University of Miami

Problem 71

Name each alcohol.

Ly T.
Numerade Educator

Problem 72

Draw the structure for each alcohol.
a. 2-butanol
b. 2-methyl-1-propanol
c. 3-ethyl-1-hexanol
d. 2-methyl-3-pentanol

Keenan M.
University of Miami

Problem 73

List the products of each alcohol reaction.

Ly T.
Numerade Educator

Problem 74

List the products of each alcohol reaction.

Keenan M.
University of Miami

Problem 75

Name each aldehyde or ketone.

Ly T.
Numerade Educator

Problem 76

Draw the structure of each aldehyde or ketone.
a. hexanal
b. 2-pentanone
c. 2-methylbutanal
d. 4-heptanone

Keenan M.
University of Miami

Problem 77

Determine the product of the addition reaction.

Ly T.
Numerade Educator

Problem 78

Determine the product of the addition reaction.

Keenan M.
University of Miami

Problem 79

Name each carboxylic acid or ester.

Ly T.
Numerade Educator

Problem 80

Draw the structure of each carboxylic acid or ester.
a. pentanoic acid
b. methyl hexanoate
c. 3-ethylheptanoic acid
d. butyl ethanoate

Keenan M.
University of Miami

Problem 81

Determine the products of each carboxylic acid reaction.

Ly T.
Numerade Educator

Problem 82

Determine the products of each carboxylic acid reaction.

Keenan M.
University of Miami

Problem 83

Name each ether.

Ly T.
Numerade Educator

Problem 84

Draw the structure for each ether.
a. ethyl propyl ether
b. dibutyl ether
c. methyl hexyl ether
d. dipentyl ether

Keenan M.
University of Miami

Problem 85

Name each amine.

Ly T.
Numerade Educator

Problem 86

Draw the structure for each amine.
a. isopropylamine
b. triethylamine
c. butylethylamine

Keenan M.
University of Miami

Problem 87

Classify each amine reaction as acid-base or condensation and list its products.
a. CH3NHCH3 + HCl
b. CH3CH2NH2 + CH3CH2COOH
c. CH3NH2 + H2SO4

Ly T.
Numerade Educator

Problem 88

List the products of each amine reaction.

Keenan M.
University of Miami

Problem 89

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound.

Ly T.
Numerade Educator

Problem 90

Identify each organic compound as an alkane, alkene, alkyne, aromatic hydrocarbon, alcohol, ether, aldehyde, ketone, carboxylic acid, ester, or amine, and provide a name for the compound.

Keenan M.
University of Miami

Problem 91

Name each compound.

Ly T.
Numerade Educator

Problem 92

Name each compound.

Keenan M.
University of Miami

Problem 93

Determine whether each pair of structures are isomers or the same molecule drawn in two different ways.

Ly T.
Numerade Educator

Problem 94

Determine whether each pair of structures are isomers or the same molecule drawn two different ways.

Keenan M.
University of Miami

Problem 95

What minimum amount of hydrogen gas, in grams, is required to completely hydrogenate 15.5 kg of 2-butene?

Ly T.
Numerade Educator

Problem 96

How many kilograms of CO2 does the complete combustion of 3.8 kg of n-octane produce?

Keenan M.
University of Miami

Problem 97

Classify each organic reaction as combustion, alkane substitution, alkene addition or hydrogenation, aromatic substitution, or alcohol substitution, elimination, or oxidation.

Ly T.
Numerade Educator

Problem 98

Determine the products of each reaction.

Keenan M.
University of Miami

Problem 99

Draw the structure that corresponds to each name and indicate which structures can exist as stereoisomers.
a. 3-methyl-1-pentene
b. 3,5-dimethyl-2-hexene
c. 3-propyl-2-hexene

Ly T.
Numerade Educator

Problem 100

Identify the two compounds that display stereoisomerism and draw their structures.
a. 3-methyl-3-pentanol
b. 2-methyl-2-pentanol
c. 3-methyl-2-pentanol
d. 2-methyl-3-pentanol
e. 2,4-dimethyl-3-pentanol

Keenan M.
University of Miami

Problem 101

There are 11 structures (ignoring stereoisomerism) with the formula C4H8O that have no carbon branches. Draw the structures and identify the functional groups in each.

Ly T.
Numerade Educator

Problem 102

There are eight structures with the formula C3H7NO in which the O is part of a carbonyl group. Draw the structures and identify the functional groups in each.

Keenan M.
University of Miami

Problem 103

Explain why carboxylic acids are much stronger acids than alcohols.

Ly T.
Numerade Educator

Problem 104

The hydrogen at C-1 of 1-butyne is much more acidic than the hydrogens at C-1 in 1-butene. Explain.

Keenan M.
University of Miami

Problem 105

Determine the one or two steps it takes to get from the starting material to the product using reactions found in this chapter.

Ly T.
Numerade Educator

Problem 106

Given the following synthesis of ethyl 3-chloro-3-methylbutanoate, fill in the missing intermediates or reactants.

Keenan M.
University of Miami

Problem 107

For the chlorination of propane, the two isomers shown here are possible.

Propane has six hydrogen atoms on terminal carbon atoms- called primary (1) hydrogen atoms-and two hydrogen atoms on the interior carbon atom-called secondary (2) hydrogen atoms.
a. If the two different types of hydrogen atoms were equally reactive, what ratio of 1-chloropropane to 2-chloropropane would we expect as monochlorination products?
b. The result of a reaction yields 55% 2-chloropropane and 45% 1-chloropropane. What can we conclude about the relative reactivity of the two different kinds of hydrogen atoms? Determine a ratio of the reactivity of one type of hydrogen atom to the other.

Ly T.
Numerade Educator

Problem 108

There are two isomers of C4H10. Suppose that each isomer is treated with Cl2 and the products that have the composition C4H8Cl2 are isolated. Find the number of different products that form from each of the original C4H10 compounds. Do not consider optical isomerism.

Keenan M.
University of Miami

Problem 109

Identify the compounds formed in the previous problem that are chiral.

Check back soon!

Problem 110

Nitromethane has the formula CH3NO2, with the N bonded to the C and without O-O bonds. Draw its two most important contributing structures.
a. What is the hybridization of the C, and how many hybrid orbitals are in the molecule?
b. What is the shortest bond?
c. Between which two atoms is the strongest bond found?
d. Predict whether the HCH bond angles are greater or less than 109.5  and justify your prediction.

Keenan M.
University of Miami

Problem 111

Free radical fluorination of methane is uncontrollably violent, and free radical iodination of methane is a very poor reaction. Explain these observations in light of bond energies.

Ly T.
Numerade Educator

Problem 112

There are two compounds with the formula C3H6, one of which does not have a multiple bond. Draw its structure and explain why it is much less stable than the isomer with the double bond.

Keenan M.
University of Miami

Problem 113

Consider molecules that have two carbons and two chlorines. Draw the structures of three of these with no dipole moment and two with a dipole moment.

Ly T.
Numerade Educator

Problem 114

Pick the more oxidized structure from each pair.

Keenan M.
University of Miami

Problem 115

Draw the structure and name a compound with the formula C8H18 that forms only one product with the formula C8H17Br when it is treated with Br2.

Ly T.
Numerade Educator

Problem 116

Determine whether each structure is chiral.

Keenan M.
University of Miami

Problem 117

Have each group member select a different functional group. Individually, draw and name a compound containing your functional group. Pass your drawing to the group member on your right and your compound name to the group member on your left. Name the compound for the drawing you received and draw the compound whose name you received.

Check back soon!

Problem 118

Using complete sentences, compare and contrast each of the following, mentioning at least two similarities and two differences for each:
a. salt and sugar
b. methane and 3-methylheptane
c. aldehydes and ketones

Keenan M.
University of Miami

Problem 119

The octane rating for gasoline is a measurement of how readily a fuel combusts compared to 2,2,4-trimethylpentane, an isomer of octane.
a. Draw 2,2,4-trimethylpentane and verify that it is an isomer of octane.
b. Draw four other isomers of octane.
c. Select one of the isomers and draw it such that it looks different on the page but is still the exact same compound.
d. Name this isomer.
e. Define isomer using a complete sentence.

Ly T.
Numerade Educator

Problem 120

Working individually, have each group member select from the chapter a reaction characteristic of a particular organic functional group. Individually, write out your reaction with one of the following left as a blank: one reactant, one product, or reaction conditions. Pass your reaction to the group member on
your right. Fill in the blank of the reaction you have received.

Keenan M.
University of Miami

Problem 121

Ester compounds often have a sweet, pleasant odor. Many characteristic fruit scents are largely due to the natural presence of one or more ester compounds. As such, artificial scents for foods are often composed of complex mixtures of various esters. The exact identity and ratio of ingredients that compose a particular scent are closely guarded secrets in the food and fragrance industry.

Suppose that you are a chemist working for a company that is creating a new line of air fresheners. The company is considering three scents: apple, pear, and pineapple. The project manager has asked you to prepare the ester compounds that are largely responsible for these scents. The structural formulas for these ester compounds are shown here:

To prepare these esters, you have been given the alcohols listed in the table and an adequate supply of all other necessary reagents, solvents, and equipment.

Use the structural formulas of the alcohols and information in the table to answer these questions:
a. Provide a name for each ester that you will prepare.
b. Draw the structure of each alcohol listed in the table.
c. Determine the procedure you will use to prepare each ester, using the reactions found in this chapter. (Hint: Recall that esters are derived from a carboxylic acid and an alcohol.)
d. Calculate the cost to prepare 100.0 g of each ester. Which one will be the most expensive to prepare? Which ester will be the least expensive? (Consider only the cost of the alcohols in the table, and disregard the costs of other reagents. Assume 100% yield for all reactions.)

Ly T.
Numerade Educator