Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 6, Problem 6.51P
In this chapter, we studied the mechanism of the acid-catalyzed hydration of an
Propene
2-Propanol
(Isopropyl alcohol)
Propose a mechanism for the acid-catalyzed dehydration of 2-propanol to propene.
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Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second
molecule of alcohol gives an acetal and a molecule of water.
ROH, H+
OH
OR
Aldehyde/ketone
Alcohol
ROH, H+
Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds:
OH
OH
OR
OR
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
+ H₂O
Esterication is the reaction of a carboxylic acid (RCOOH) with an alcohol (R'OH) to form an ester (RCOOR') with loss of water. Equation [1] is an example of an intermolecular esterication reaction. Equation [2] is an example of an intramolecular esterication reaction; that is, the carboxylic acid and alcohol are contained in the same starting material, forming a cyclic ester as product. The equilibrium constants for both reactions are given. Explain why Keq is different for these two apparently similar reactions.
In an esterification reaction, a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. Draw the structure of the ester product in the reaction between pentanoic acid and 1‑propanol.
pentanoic acid+ 1-propanol= ester+ H20
structure of ester product needed
Chapter 6 Solutions
Organic Chemistry
Ch. 6.2 - Using the BDE values from Appendix 3, calculate...Ch. 6.3 - Name and draw a structural formula for the product...Ch. 6.3 - Prob. 6.3PCh. 6.3 - Propose a mechanism for the addition of HI to...Ch. 6.3 - Prob. 6.5PCh. 6.3 - Propose a mechanism for the acid-catalyzed...Ch. 6.3 - The acid-catalyzed hydration of...Ch. 6.3 - Complete these reactions. (a) (b)Ch. 6.3 - Draw the structure of the chlorohydrin formed by...Ch. 6.4 - Draw structural formulas for the alkene that gives...
Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Prob. 6.53PCh. 6 - Prob. 6.54P
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- Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forwardMixing cyclohexanol with phosphoric acid is an exothermic process, whereas the production of cyclohexene is endothermic. Construct an energy diagram showing the course of this reaction. Label the diagram with the starting alcohol, the oxonium ion (the protonated alcohol), the carbocation, and the product.arrow_forwardKinetics and thermodynamics H+ catatylzes the esterification reaction of alcohols with carboxylic acids. Describe at least two ways the addition of H+ can increase the rate of the reaction. based on the imagearrow_forward
- Give the reaction equation of an acid catalyzed reaction of 2-methyl-2-butene with methanolarrow_forward1-Bromopropane is synthesized by treating 1-propanol with sulfuric acid (H2SO4) and potassium bromide (KBr) through a simple distillation. What is the inorganic by-product left in the reaction flask following the distillation?arrow_forwardWrite the chemical equation for the reaction of ethanoic acid with N-methylethanamine. Which is formula of this rule of reaction?arrow_forward
- Which compound is a tertiary alcohol that may not be oxidized by H2CrO4 or MnO2? Which compound is a secondary alcohol that may be oxidized to a ketone by MnO2? Which compound is an alcohol that may be oxidized to an aldehyde by PCC?arrow_forwardAlkyl sulfonates undergo the same type of substitution reactions as alkyl halides and can also be prepared from alcohols. What advantage does the preparation of an alkyl sulfonate from an alcohol have over the preparation of an alkyl halide from an alcohol?arrow_forwardConvert the alcohol, n-propanol, to n-propyl fluoride in 2 steps. List the reagents in the order you would use them.arrow_forward
- Phenols are aromatic rings with an alcohol functional group attached directly to the ring. These compounds have unique acidity and solubility for alcohol groups. Predict the solubility of this phenol in water.arrow_forwardPredict the products when 1-propanol is heated in the presence of H . Include all hydrogen atoms in your structure. Show both the organic product and the inorganic product formed in this reaction.arrow_forwardBriefly describe the preparation of alcohols from ketones, and the preparation of alcohols from esters, each using the same Grignard reagent CH3CH2MgCl. Show an example reaction equation involving your own chosen ketone and ester molecules,respectively, to illustrate your descriptionarrow_forward
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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY