ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 6, Problem 6.57P
Interpretation Introduction
Interpretation: The reason for the different
Concept introduction: The change in Gibbs free energy is represented by
If the
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b)
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5. Complete the following oxidation reactions for alcohols. Draw the structure of the product.
Name the reactant and identify the type of compound formed in the product.
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CHy
CH3
Ester formation and ester hydrolysis are exactly the same reaction only written in reverse.
General reaction of ester formation:
H*, heat
R—с—он + Н—о—R'
R—с—о-R' + H,O
carboxylic
acid
alcohol
carboxylic
or phenol
ester
General reaction of ester hydrolysis:
||
R—с—OR' + H—оН
R—с—оН +R—ОH
ester
carboxylic
acid
alcohol
or phenol
What determines which direction the reaction proceeds and what actually forms?
o the boiling point of the carboxylic acid
o the presence (or absence) of heat as well as the concentration of reactants and products
o the molecular weight of reactants and products
o the presence (or absence) of heat as well as the catalyst
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.…
Chapter 6 Solutions
ORGANIC CHEMISTRY
Ch. 6 - Problem 6.1 Classify each transformation as...Ch. 6 - Prob. 6.2PCh. 6 - Problem 6.3 By taking into account...Ch. 6 - Problem 6.4 Use curved arrows to show the movement...Ch. 6 - Problem 6.5 Follow the curved arrows and draw the...Ch. 6 - Prob. 6.6PCh. 6 - Problem 6.7 Use the values in Table 6.2 to...Ch. 6 - Prob. 6.8PCh. 6 - aWhich Keq corresponds to a negative value of G,...Ch. 6 - Given each of the following values, is the...
Ch. 6 - Given each of the following values, is the...Ch. 6 - The equilibrium constant for the conversion of the...Ch. 6 - Prob. 6.13PCh. 6 - For a reaction with H=40kJ/mol, decide which of...Ch. 6 - For a reaction with H=20kJ/mol, decide which of...Ch. 6 - Draw an energy diagram for a reaction in which the...Ch. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Problem 6.19 Consider the following energy...Ch. 6 - Draw an energy diagram for a two-step reaction,...Ch. 6 - Which value if any corresponds to a faster...Ch. 6 - Prob. 6.22PCh. 6 - Problem 6.23 For each rate equation, what effect...Ch. 6 - Prob. 6.24PCh. 6 - Identify the catalyst in each equation. a....Ch. 6 - Draw the products of homolysis or heterolysis of...Ch. 6 - Explain why the bond dissociation energy for bond...Ch. 6 - Classify each transformation as substitution,...Ch. 6 - Prob. 6.29PCh. 6 - 6.30 Draw the products of each reaction by...Ch. 6 - 6.31 (a) Add curved arrows for each step to show...Ch. 6 - Prob. 6.32PCh. 6 - Prob. 6.33PCh. 6 - Prob. 6.34PCh. 6 - Calculate H for each reaction. a HO+CH4CH3+H2O b...Ch. 6 - Homolysis of the indicated CH bond in propene...Ch. 6 - Prob. 6.37PCh. 6 - Prob. 6.38PCh. 6 - 6.39. a. Which value corresponds to a negative...Ch. 6 - Prob. 6.40PCh. 6 - For which of the following reaction is S a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - 6.44 Consider the following reaction: .
Use curved...Ch. 6 - Prob. 6.45PCh. 6 - Draw an energy diagram for the Bronsted-Lowry...Ch. 6 - Prob. 6.47PCh. 6 - Indicate which factors affect the rate of a...Ch. 6 - Prob. 6.49PCh. 6 - 6.50 The conversion of acetyl chloride to methyl...Ch. 6 - Prob. 6.51PCh. 6 - Prob. 6.52PCh. 6 - The conversion of (CH3)3Cl to (CH3)2C=CH2 can...Ch. 6 - 6.54 Explain why is more acidic than , even...Ch. 6 - Prob. 6.55PCh. 6 - Prob. 6.56PCh. 6 - Prob. 6.57PCh. 6 - Although Keq of equation 1 in problem 6.57 does...Ch. 6 - Prob. 6.59P
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- 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 casearrow_forward1. Most margarines have been hydrogenated to maintain a soft, homogeneous mixture. While the product is easy to spread, this has made the product an unhealthy choice. A hydrogenation reaction is used to convert an alkene to an alkane. a carboxylic acid to an aldehyde. an alkene to a ketone an aromatic hydrocarbon to a linear hydrocarbonarrow_forwardClassify each of the following molecules as alcohol,aldehyde, ketone, carboxylic acid, amine, or ether.arrow_forward
- Consider the following reactions: When C5H12 is reacted with Cl2(g) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of C5H12 in this reaction? When C4H8 is reacted with H2O, a tertiary alcohol is produced as the major product. What is the structure of C4H8 in this reaction? When C7H12 is reacted with HCl, 1-chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for C7H12 in this reaction? When a hydrocarbon is reacted with water and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? When C5H12O is oxidized, a carboxylic acid is produced. What are the possible structures for C5H12O in this reaction?arrow_forwardLSaxw_byUjt4NKKTEABPFImknTAVIxeSATH3-MO9AEbrFOXuga ponse TUIse The structure of glycogen is very similar to that of amylose Secondary alcohols are readily oxidized with common oxidizing agents to carboxylic acids Amines react with strong acids such as HCI, to form ammonium salts In general, oils come from animal sources and fats from vegetable sources Amines are weak bases, they are considerably more basic than alcohols, and water Carboxylic acids are less acidic than alcohols Steroids are lipids that do not contain fatty acids Alkylamines have boiling points are higher than those of alkanes, but lower than those of alcohols 4- Tio druck & 1 8. 9. Y ! OX { Hi J K : NI pause O O O O O O O O OOarrow_forwardI need help with number 9 part B. Which was the formula of the oxidizing agents, such as CrO3, MnO4 - , or enzymes can oxidized primary alcohols to produce carboxylic acids. Draw the structure of the carboxylic acid that is formed when the alcohol shown below is oxidized?arrow_forward
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