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Reactions of Alcohols

The reactions of alcohols are numerous and are classified according to the functional group of the alcohol, the nature of the reactant and the reaction temperature. Many reactions of alcohols involve the cleavage of C-C bond at the position adjacent to the hydroxyl group:

Oxidation States of Alcohols and Related Functional Groups

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Oxidation of Alcohols

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06:57
Introduction to General, Organic and Biochemistry

Answer true or false.
(a) The two most important reactions of alcohols are their acid-catalyzed dehydration to give alkenes and their oxidation to aldehydes, ketones, and carboxylic acids.
(b) The acidity of alcohols is comparable to that of water.
(c) Water-insoluble alcohols and water-insoluble phenols react with strong bases to give watersoluble salts.
(d) Acid-catalyzed dehydration of cyclohexanol gives cyclohexane.
(e) When the acid-catalyzed dehydration of an alkene can yield isomeric alkenes, the alkene with the greater number of hydrogens on the carbons of the double bond generally predominates.
(f) The acid-catalyzed dehydration of 2-butanol gives predominantly 1-butene.
(g) The oxidation of a primary alcohol gives either an aldehyde or a carboxylic acid depending on experimental conditions.
(h) The oxidation of a secondary alcohol gives a carboxylic acid.
(i) Acetic acid, $\mathrm{CH}_{3} \mathrm{COOH}$, can be prepared from ethylene, $\mathrm{CH}_{2}=\mathrm{CH}_{2}$, by treatment of ethylene with $\mathrm{H}_{2} \mathrm{O} / \mathrm{H}_{2} \mathrm{SO}_{4}$, followed by treatment with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7} / \mathrm{H}_{2} \mathrm{SO}_{4}$
(j) Treatment of propene, $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}$, with $\mathrm{H}_{2} \mathrm{O} /$
$\mathrm{H}_{2} \mathrm{SO}_{4}$ followed by treatment with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{2} / \mathrm{H}_{2} \mathrm{SO}_{4}$
gives propanoic acid, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}$

Alcohols, Ethers, and Thiols
Sana Riaz
03:34
Organic Chemistry

Heating an alcohol with sulfuric acid is a good way to prepare a symmetrical ether such as diethyl ether.
a. Explain why it is not a good way to prepare an unsymmetrical ether such as ethyl propyl ether.
b. How would you synthesize cthyl propy1 cther?

Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Tom Rutherford
04:33
Organic Chemistry

Fill in the blank with "oxidized" or "reduced."
a. Secondary alcohols are __________ to ketones.
b. Acyl halides are __________ to aldehydes.
c. Aldehydes are __________ to primary alcohols.
d. Alkenes are __________ to aldehydes and/or ketones.
e. Aldehydes are __________ to carboxylic acids.
f. Alkenes are __________ to 1,2-diols.
g. Alkenes are __________ to alkanes.

More About Oxidation–Reduction Reactions
Nicholas Sacco

Additional Methods for Oxidizing Alcohols

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Biological Oxidation of Alcohols

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Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates

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Reduction of Alcohols

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04:44
Organic Chemistry

Draw the product formed when the $\alpha,\beta$-unsaturated ketone $\textbf{A}$ is treated with each reagent.
a. NaBH$_4$, CH$_3$OH
b. H$_2$ (1 equiv), Pd-C
c. H$_2$ (excess), Pd-C
d. [1] CH$_3$Li; [2] H$_2$O
e. [1] CH$_3$CH$_2$MgBr; [2] H$_2$O
f. [1] (CH$_2$=CH)$_2$CuLi; [2] H$_2$O

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction
Ian Kaigh

Reactions of Alcohols with Hydrohalic Acids

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07:18
Organic Chemistry

Show how 1-pentanol could be transformed into each of the following compounds. (You may use any needed inorganic reagents and you need not show the synthesis of a particular compound more than once.)
(a) 1 -Bromopentane
(b) 1 -Pentene
(c) 2 -Pentanol
(d) Pentane
(e) 2 -Bromopentane
(f) $1-$ Hexanol
(g) 1 -Heptanol
(h) Pentanal
(i) 2 -Pentanone
(i) Pentanoic acid
(k) Dipentyl ether (two ways)
(1) 1 -Pentyne
(m) 2 -Bromo-1-pentene
(n) Pentyllithium
(o) 4 -Methyl-4-nonanol

Alcohols from Carbonyl Compounds
Lottie Adams

Reactions of Alcohols with Phosphorus Halides

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05:59
Organic Chemistry

Explain why the ether obtained by treating an optically active alcohol with $\mathrm{PBr}_{3}$ in pyridine followed by sodium methoxide has the same configuration as the alcohol, whereas the cther obtained by treating the alcohol with tosyl chloride followed by sodium methoxide has a configuration opposite that of the alcohol.

Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Tom Rutherford

Reactions of Alcohols with Thionyl Chloride

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Dehydration Reactions of Alcohols

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02:43
Organic Chemistry

Suggest a name for alcohol dehydrogenase that would refer to the forward reaction - that is, that would refer to the conversion of acetaldehyde to ethanol.

The Organic Chemistry of the Metabolic Pathways
Prashant Bana
09:44
Organic Chemistry

Indicate which alcohol in each pair undergoes an elimination reaction more rapidly when heated with $\mathrm{H}_{2} \mathrm{SO}_{4}$

Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Tom Rutherford
02:39
Organic Chemistry

What product would be formed if the preceding alcohol were heated with an equivalent amount of HBr rather than with a catalytic amount of $\mathrm{H}_{2} \mathrm{SO}_{4} ?$

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds
Nicholas Sacco

Unique Reactions of Diols

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04:28
Organic Chemistry

1,2-Diols are converted to carbonyl compounds when treated with strong acids, in a reaction called the $pinacol$ $rearrangement$. (a) Draw a stepwise mechanism for this reaction. (Hint: The reaction proceeds by way of carbocation intermediates.) (b) Assuming that the pinacol rearrangement occurs via the more stable carbocation, draw the rearrangement product formed from diol $D$.

Alcohols, Ethers, and Epoxides
Ly Tran

Esterification of Alcohols

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05:53
Organic Chemistry

How could you synthesize isopropy1 propyl cther, using isopropyl alcohol as the only carbon-containing reagent?

Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Tom Rutherford
00:58
Living by Chemistry

Below are the structural formulas for four esters. Write the correct molecular formula for each one.
a. Image is not available to copy
b. Image is not available to copy
c. Image is not available to copy
d. Image is not available to copy

Speaking of Molecules
Analyzing Ester Synthesis
David Collins

Esters of Inorganic Acids

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05:41
Introduction to General, Organic and Biochemistry

(Chemical Connections 19 A) Locate the ester group in pyrethrin I and draw a structural formula for chrysanthemic acid, the carboxylic acid from which this ester is derived.

Carboxylic Anhydrides, Esters, and Amides
Sana Riaz
06:40
Organic Chemistry

The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an $\alpha$ -bromo ester with zinc. Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

Reactions at the $\alpha$ -Carbon
Tom Rutherford
04:07
Organic Chemistry

Explain why the $\alpha$ -hydrogen of an $N, N$ -disubstituted amide is less acidic $\left(\mathrm{p} K_{\mathrm{a}}=30\right)$ than the $\alpha$ -hydrogen
of an ester $\left(\mathrm{p} K_{\mathrm{a}}=25\right)$

Reactions at the $\alpha$ -Carbon
Tom Rutherford

Reactions of Alkoxides

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