Chemistry with Access Code, Hybrid Edition
9th Edition
ISBN: 9781285188492
Author: Steven S. Zumdahl
Publisher: CENGAGE L
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Chapter 22, Problem 156CP
Alcohols are very useful starting materials for the production of many different compounds. The following conversions, starting with 1-butanol, can be carried out in two or more steps. Show the steps (reactants/catalysts) you would follow to carry out the conversions, drawing the formula for the organic product in each step. For each step, a major product must be produced. (See Exercise 62.) (Hint: In the presence of H+, an alcohol is converted into an
a. 1-butanol → butane
b. 1-butanol → 2-butanone
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1. Dehydration:
2. Oxidation:
This is a reaction where an alcohol loses a water molecule to
form an alkene.
For example, when ethanol is treated with an acidic catalyst,
such as sulfuric acid, it undergoes dehydration to form
ethene (CH2=CH2) and water.
ALCOHOLS
In this reaction, an alcohol is converted to either a carbonyl
compound or a carboxylic acid.
3. Esterification:
Types of Reaction (s)
For example, primary alcohols can be oxidized to aldehydes
or carboxylic acids, while secondary alcohols can be oxidized
to ketones. Tertiary alcohols are usually not affected by
oxidations
4. Substitution:
The conversion of an alcohol and a carboxylic acid to an
ester and water, in the presence of an acid catalyst.
The reaction between methanol and acetic acid to form
methyl acetate: CH3OH + CH3COOH CH3COOCH3 + H2O
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ME
Substitution reactions in organic chemistry involve the
replacement of one atom or group of atoms with another
atom or group of atoms in a molecule.
1.…
How does the structure of an alcohol differ from an ether?
Describe how an aldehyde differs in structure from a ketone.
Thiols are compounds which resemble alcohols, except that the oxygen atom is replaced by a sulfur atom. Draw the analogous thiol for the four carbon alcohol in Table 1.
Describe the structural difference between carboxylic acids and esters.
Are ethers polar molecules?
Would you expect ethers to have higher or lower boiling points than alkanes (circle one)? Explain.
Pentane (an alkane) has a boiling point of 36 °C. Does the data agree with your prediction? explain why this could be the case
Gasohol is a mixture of 90% gasoline and 10% ethanol, CH 3CH 2OH. Ethanol is considered an environmentally friendly fuel additive because it can be made from a renewable source—sugarcane. Ethanol burns in air to form CO 2 and H 2O, and, like the combustion of alkanes, this reaction also releases a great deal of energy. Write a balanced equation for the combustion of ethanol.
Chapter 22 Solutions
Chemistry with Access Code, Hybrid Edition
Ch. 22 - What is a hydrocarbon? What is the difference...Ch. 22 - Prob. 2RQCh. 22 - What are aromatic hydrocarbons? Benzene exhibits...Ch. 22 - Summarize the nomenclature rules for alkanes,...Ch. 22 - What functional group distinguishes each of the...Ch. 22 - Distinguish between isomerism and resonance....Ch. 22 - Prob. 7RQCh. 22 - Prob. 8RQCh. 22 - Prob. 9RQCh. 22 - Prob. 10RQ
Ch. 22 - Prob. 11RQCh. 22 - Describe the structural differences between DNA...Ch. 22 - Prob. 1QCh. 22 - Prob. 2QCh. 22 - Prob. 3QCh. 22 - Prob. 4QCh. 22 - Prob. 5QCh. 22 - Prob. 6QCh. 22 - Prob. 7QCh. 22 - Give an example reaction that would yield the...Ch. 22 - Prob. 9QCh. 22 - Prob. 10QCh. 22 - Prob. 11QCh. 22 - Prob. 12QCh. 22 - Prob. 13ECh. 22 - Prob. 14ECh. 22 - Draw all the structural isomers for C8H18 that...Ch. 22 - Draw all the structural isomers for C8H18 that...Ch. 22 - Prob. 17ECh. 22 - Prob. 18ECh. 22 - Draw the structural formula for each of the...Ch. 22 - Prob. 20ECh. 22 - Prob. 21ECh. 22 - Name each of the following cyclic alkanes, and...Ch. 22 - Prob. 23ECh. 22 - Draw the structures for two examples of...Ch. 22 - Name each of the following alkenes. a. CH2 = CH ...Ch. 22 - Name each of the following alkenes or alkynes. a....Ch. 22 - Prob. 27ECh. 22 - Give the structure for each of the following. a....Ch. 22 - Prob. 29ECh. 22 - Cumene is the starting material for the industrial...Ch. 22 - Name each of the following. a. b. CH3CH2CH2CCl3 c....Ch. 22 - Prob. 32ECh. 22 - There is only one compound that is named...Ch. 22 - Prob. 34ECh. 22 - Prob. 35ECh. 22 - Prob. 36ECh. 22 - Draw all the structural isomers of C5H10. Ignore...Ch. 22 - Prob. 38ECh. 22 - Draw all the structural and geometrical (cistrans)...Ch. 22 - Draw all the structural and geometrical (cistrans)...Ch. 22 - Draw all structural and geometrical (cistrans)...Ch. 22 - Prob. 42ECh. 22 - Prob. 43ECh. 22 - Prob. 44ECh. 22 - If one hydrogen in a hydrocarbon is replaced by a...Ch. 22 - There are three isomers of dichlorobenzene, one of...Ch. 22 - Identify each of the following compounds as a...Ch. 22 - Prob. 48ECh. 22 - Mimosine is a natural product found in large...Ch. 22 - Minoxidil (C9H15N5O) is a compound produced by...Ch. 22 - For each of the following alcohols, give the...Ch. 22 - Prob. 52ECh. 22 - Prob. 53ECh. 22 - Prob. 54ECh. 22 - Prob. 55ECh. 22 - Prob. 56ECh. 22 - Prob. 57ECh. 22 - Prob. 58ECh. 22 - Prob. 59ECh. 22 - Prob. 60ECh. 22 - Prob. 61ECh. 22 - Prob. 62ECh. 22 - Prob. 63ECh. 22 - Prob. 64ECh. 22 - Prob. 65ECh. 22 - Prob. 66ECh. 22 - Prob. 67ECh. 22 - Prob. 68ECh. 22 - Prob. 69ECh. 22 - Prob. 70ECh. 22 - Prob. 71ECh. 22 - Prob. 72ECh. 22 - Super glue contains methyl cyanoacrylate, which...Ch. 22 - Prob. 74ECh. 22 - Prob. 75ECh. 22 - Prob. 76ECh. 22 - Prob. 77ECh. 22 - Prob. 78ECh. 22 - Prob. 79ECh. 22 - Prob. 80ECh. 22 - Prob. 81ECh. 22 - Prob. 82ECh. 22 - Prob. 83ECh. 22 - Prob. 84ECh. 22 - Aspartame, the artificial sweetener marketed under...Ch. 22 - Prob. 86ECh. 22 - Prob. 87ECh. 22 - Draw the structures of the tripeptides glyalaser...Ch. 22 - Prob. 89ECh. 22 - Prob. 90ECh. 22 - Give an example of amino acids that could give...Ch. 22 - What types of interactions can occur between the...Ch. 22 - Prob. 93ECh. 22 - Prob. 94ECh. 22 - Prob. 95ECh. 22 - Prob. 96ECh. 22 - Prob. 97ECh. 22 - Prob. 98ECh. 22 - Prob. 99ECh. 22 - Prob. 100ECh. 22 - Prob. 101ECh. 22 - Prob. 102ECh. 22 - Prob. 103ECh. 22 - Prob. 104ECh. 22 - Prob. 105ECh. 22 - Prob. 106ECh. 22 - Prob. 107ECh. 22 - Prob. 108ECh. 22 - The base sequences in mRNA that code for certain...Ch. 22 - Prob. 110ECh. 22 - Prob. 111AECh. 22 - Prob. 112AECh. 22 - Prob. 113AECh. 22 - Prob. 114AECh. 22 - Prob. 115AECh. 22 - Prob. 116AECh. 22 - Explain why methyl alcohol is soluble in water in...Ch. 22 - Prob. 118AECh. 22 - Prob. 119AECh. 22 - Prob. 120AECh. 22 - Prob. 121AECh. 22 - Prob. 122AECh. 22 - Prob. 123AECh. 22 - Prob. 124AECh. 22 - Prob. 125AECh. 22 - Prob. 126AECh. 22 - Prob. 127AECh. 22 - Prob. 128AECh. 22 - Prob. 129AECh. 22 - a. Use bond energies (see Table 3-3) to estimate H...Ch. 22 - Prob. 131AECh. 22 - Prob. 132AECh. 22 - All amino acids have at least two functional...Ch. 22 - Prob. 134AECh. 22 - Prob. 135AECh. 22 - In glycine, the carboxylic acid group has Ka = 4.3...Ch. 22 - Name each of the following alkanes. a....Ch. 22 - Prob. 138CWPCh. 22 - Name each of the following cyclic alkanes. a. b....Ch. 22 - Name each of the following alkenes and alkynes. a....Ch. 22 - a. Name each of the following alcohols. b. Name...Ch. 22 - Prob. 142CWPCh. 22 - Prob. 143CWPCh. 22 - Prob. 144CWPCh. 22 - Prob. 145CPCh. 22 - Prob. 146CPCh. 22 - Prob. 147CPCh. 22 - Consider a sample of a hydrocarbon at 0.959 atm...Ch. 22 - Prob. 149CPCh. 22 - Prob. 150CPCh. 22 - Prob. 151CPCh. 22 - Prob. 152CPCh. 22 - Prob. 153CPCh. 22 - Prob. 154CPCh. 22 - Prob. 155CPCh. 22 - Alcohols are very useful starting materials for...Ch. 22 - A chemical breathalyzer test works because ethanol...Ch. 22 - Estradiol is a female hormone with the following...Ch. 22 - Prob. 159IPCh. 22 - Prob. 160IPCh. 22 - Prob. 161MPCh. 22 - Prob. 162MP
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- Alcohols A, B and C all have the composition C4H 100. Molecules of alcohol A contain a branched carbon chain and can be oxidized to an aldehyde; molecules of alcohol B contain a linear carbon chain and can be oxidized to a ketone; and molecules of alcohol C can be oxidized to neither an aldehyde nor a ketone. Write the Lewis structures of these molecules.arrow_forward. With very reactive agents, such as the halogen elements, alkanes undergo reactions, whereby a new atom rep laces one or more hydrogen atoms of the alkane.arrow_forwardOrganic compounds that contain double or triple carbon- carbon bonds are called ____ compounds. The name of the alkene with the formula CH3-CH=CH-CH2 -CH3 is ____. Organic compounds that contain the benzene ring are called ____compounds.arrow_forward
- Identify the organic functional groups and reaction type for the following reaction.The reactant is a(n)a. secondary alcohol and ketoneb. secondary alcohol and aldehydec. tertiary alcohol and ketoned. primary alcohol and ketonee. ether and carboxylic acidf. tertiary alcohol and aldehydeg. primary alcohol and aldehydeThe product is a(n)a. carboxylic acidsb. ketone and carbioxylic acidc. ether and carboxylic acidd. ketone and aldehydee. secondary alcohol and carboxylic acidf. secondary alcohol and ketoneThe reaction type is:a. hydrolysisb. reduction (hydrogenation)c. esterificationd. dehydratione. hydrationf. oxidationg. amide synthesisarrow_forwardHE 132 cohols, Aldehydes, Ketones 1. An unknown organic compound has the molecular formula C4H100. It resists oxidation and it can undergo dehydration to form an alkene. Draw the structure for the compound and write equations for the reactions described. Name the reactant and product. 2. An unknown organic compound has the molecular formula C4H8O. It resists oxidation and it can be reduced with H2 to form an alcohol. Draw the structure for the compound and write equations for the reactions described. Name the reactant and product. 3. Draw the structures for 2,3-dimethylhexanal undergoing the followiìng reactions: Oxidation Reduction with H2 4. Draw the structures for 2-methyl-3-hexanol undergoing the following reactions: Intramolecular dehydration Oxidation 5. Rank the following from lowest to highest boiling point. Explain your ranking. Butanal, 1-butanol, butane 6. Both ethane and ethanol contain 2 carbon atoms. Ethane is a gas at room temperature and is insoluble in water, whereas…arrow_forwardGiven the organic chemical reaction, give the products.arrow_forward
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