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Lecture

Topic 5 Summary: "Alcohols, Ethers & Thiols"

2 Pages
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Department
Chemistry
Course Code
Chemistry 1027A/B
Professor
Mel Usselman

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Key Concepts In Organic Chemistry: Alcohols, Ethers & Thiols
(Usselman Version)
-Alcohols have the general formula R-OH. The O atom is always ignored in calculations of units of
unsaturation. The O in alcohols is sp3 hybridized (two sp3 orbitals are occupied by non-bonding pairs).
Thiols have the general formula R-SH. The S atom is always ignored in calculations of units of
unsaturation. In alcohol/thiol naming, the OH/SH group always takes priority over π bonds. Alcohols are
classed as 1°, 2° or 3° depending on the type of sp3 C atom to which the OH group is bonded.
-Hydrogen bond refers to the attractive force between an Hδ+ of one functional group and the δ- of the
lone pair on the O (or other) atom of another. A hydrogen bond is not a true (σ) bond, but is instead a
coulombic attraction between partial charges on atoms in neighbouring molecules.
-Alcohols tend to have very high boiling points for their size. OH groups greatly increase the solubility of
organic molecules in water. One of the most noteworthy physical feature of thiols is their incredibly
terrible smell.
-Like H2O, alochols and thiols are amphiprotic, they can function as acids (in the presence of sufficiently
strong bases) or as bases (in the presence of sufficiently strong acids). Alcohols, like water, also react
with Group 1 and 2 metals to form alkoxide salts, with the liberation of hydrogen:
ROH + Na RO-Na+ + 1/2H2
-The conversion of alcohols to alkyl halides is a substitution reaction that proceeds by an SN1 or an SN2
mechanism, depending on the structure of the alcohol. In the reaction of alcohol with HX (X = Cl, Br, I),
tertiary alcohols react by an SN1 mechanism, but only after the hydroxyl group is protonated to make an
oxonium ion. This converts the OH to an excellent LG, OH2. Primary and secondary alcohols also give
alkyl halides on reaction with HX, but an SN1 mechanism is energetically unfavourable and an SN2
mechanism occurs instead.
-In the reaction of alcohol with thionyl chloride, SOCl2, better yields are obtained from 1° or 2° (but not
) because coproducts bubble out of solution, making the reaction irreversible. It occurs by SN2
mechanism.
-In the dehydration of alcohols to alkenes, heating (Δ) is required (as in Lab #3). This reaction undergoes
elimination to form double bonds (especially favoured) only when stable double bonds are formed (the
product with the most alkyl groups will form).
-1° and 2° alcohols are easily oxidized to carbonyl compounds. Because oxidation removes an H atom
from both the O atom and the C atom, only 1° and 2° alcohols react; 3° alcohols cannot be oxidized to
simple carbonyl compounds. PCC is an oxidizing agent that has been developed to oxidize 1° alcohols to
aldehydes only, thus solving the practical problem of 1° alcohol oxidation.
-Thiols are not oxidized to thiones (C = S), but instead to disulfides (RS-SR). Disulfides can also be
reduced back to thiols through the use of reducing agents.

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Description
Key Concepts In Organic Chemistry: Alcohols, Ethers & Thiols (Usselman Version) -Alcohols have the general formula R-OH. The O atom is always ignored in calculations of units of 3 3 unsaturation. The O in alcohols is sp hybridized (two sp orbitals are occupied by non-bonding pairs). Thiols have the general formula R-SH. The S atom is always ignored in calculations of units of unsaturation. In alcohol/thiol naming, the OH/SH group always takes priority over π bonds. Alcohols are classed as 1°, 2° or 3° depending on the type of sp C atom to which the OH group is bonded. -Hydrogen bond refers to the attractive force between an H of one functional group and the δ- of the lone pair on the O (or other) atom of another. A hydrogen bond is not a true (σ) bond, but is instead a coulombic attraction between partial charges on atoms in neighbouring molecules. -Alcohols tend to have very high boiling points for their size. OH groups greatly increase the solubility of organic molecules in water. One of the most noteworthy physical feature of thiols is their incredibly terrible smell. -Like H 2, alochols and thiols are amphiprotic, they can function as acids (in the presence of sufficiently strong bases) or as bases (in the presence of sufficiently strong acids). Alcohols, like water, also react with Group 1 and 2 metals to form alkoxide salts, with the liberation of hydrogen: - + ROH + Na RONa + 1/2H 2 -The conversion of alcohols to alkyl halides is a substitution reaction that proceeds by an SN or an SN 1 2 mechanism, depending on the structure of the alcohol. In the reaction of alcohol with HX (X = Cl, Br, I), tertiary alcohols react by an SN me1hanism, but only after the hydroxyl group is protonated to make an oxonium ion. This converts the OH to an excellent LG, OH . Prim2ry and secondary alc
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