CHM 219 Module 5
Alcohol - Correct Answer Generic formula R-OH, defined by the presence of a Hydroxyl group (-OH). Organic
derivatives of water, as one of the hydrogen atoms from the water molecule is replaced by an alkyl group.
Alcohols —> Alkyl Halides - Correct Answer -Substitution REaction , replacing the -OH with a halogen
-Alcohol (R-OH) + Hydrogen Halide (H-X) ——> alkyl halide (R-X) + water (H-OH)
-the use of Hydrogen halides promotes the substitution in two ways
1. Acid protonates the -OH of the alcohol to make it a good leaving group
2. Halide ions are good nucleophiles but weak bases so substitution is promoted over elimination
Alcohols Acidity/Basicity - Correct Answer Can act as a weak base (accepting H+ using a lone pair on the O atom) or
weak acid (donating the O-H proton as H+)
Aldehydes - Correct Answer Presence of a carbonyl group (C=O) with at least one H attached to the carbonyl C and
the remaining valence may be another H atom or an alkyl or aryl group.
Aldehydes are reduced to... - Correct Answer Primary alcohols
Alkoxide Ion - Correct Answer conjugate base of an alcohol, very strong base
Alkyloxonium Ion - Correct Answer The conjugate acid of the alcohol is often called a protonated alcohol,
All dehydration begins with... - Correct Answer Protonation of the alcohol group.
Amphoteric - Correct Answer a substance that can act as both an acid and a base
Boiling Point of Alcohols - Correct Answer High due to Hydrogen bonding between the positively charged H and
negatively charged O
Cleavage by HX - Correct Answer Typical mode of reaction is cleavage (breaking apart of the ether by severing a C-
O bond of the ether. Usually react with strong acids and heat.
Tertiary - Sn1; ether O remains with the less-hindered alkyl group and the halid bonds to the more hindered alkyl
group.
Initial products of cleavage of an ether are an alcohol and an alkyl halide.
Conversion using Phosphorous Halides (PX3) - Correct Answer X= Cl or Br
- Alcohol (3R-OH) + phosphorous trihalide (X2P-X) —> alkyl halide (3R-X) + H3PO3
-particularly efficient as one molecule of PX3 can convert 3 molecules of alcohol to the corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
Conversion using Thionyl Chloride (SOCl2) - Correct Answer Alcohol (R-OH) + Thionyl Chloride (Cl-S=O-Cl) —> alkyl
Chloride (R-Cl) + SO2 ^ + HCl
- very efficient with primary and secondary alcohols d/t the main byproduct (SO2) beig formed as a gas and leaving
the reaction mixture.
Crown Ethers - Correct Answer Can solvate cations within theur interior cavity, size of the ring controls which cations
can fit into the cavity, this allows ionic compounds to be dissolved in relatively non-polar organic solvents
Dehydration - Correct Answer Loss of water. An alcohol molecule will lose H2O to form an ALKENE. Type of
elimination reaction — lose the -OH from one C and H atom from the adjacent C.
First step — alcohol acts as a base.
Tertiary alcohols - E1
Primary alcohols - E2
Alcohol - Correct Answer Generic formula R-OH, defined by the presence of a Hydroxyl group (-OH). Organic
derivatives of water, as one of the hydrogen atoms from the water molecule is replaced by an alkyl group.
Alcohols —> Alkyl Halides - Correct Answer -Substitution REaction , replacing the -OH with a halogen
-Alcohol (R-OH) + Hydrogen Halide (H-X) ——> alkyl halide (R-X) + water (H-OH)
-the use of Hydrogen halides promotes the substitution in two ways
1. Acid protonates the -OH of the alcohol to make it a good leaving group
2. Halide ions are good nucleophiles but weak bases so substitution is promoted over elimination
Alcohols Acidity/Basicity - Correct Answer Can act as a weak base (accepting H+ using a lone pair on the O atom) or
weak acid (donating the O-H proton as H+)
Aldehydes - Correct Answer Presence of a carbonyl group (C=O) with at least one H attached to the carbonyl C and
the remaining valence may be another H atom or an alkyl or aryl group.
Aldehydes are reduced to... - Correct Answer Primary alcohols
Alkoxide Ion - Correct Answer conjugate base of an alcohol, very strong base
Alkyloxonium Ion - Correct Answer The conjugate acid of the alcohol is often called a protonated alcohol,
All dehydration begins with... - Correct Answer Protonation of the alcohol group.
Amphoteric - Correct Answer a substance that can act as both an acid and a base
Boiling Point of Alcohols - Correct Answer High due to Hydrogen bonding between the positively charged H and
negatively charged O
Cleavage by HX - Correct Answer Typical mode of reaction is cleavage (breaking apart of the ether by severing a C-
O bond of the ether. Usually react with strong acids and heat.
Tertiary - Sn1; ether O remains with the less-hindered alkyl group and the halid bonds to the more hindered alkyl
group.
Initial products of cleavage of an ether are an alcohol and an alkyl halide.
Conversion using Phosphorous Halides (PX3) - Correct Answer X= Cl or Br
- Alcohol (3R-OH) + phosphorous trihalide (X2P-X) —> alkyl halide (3R-X) + H3PO3
-particularly efficient as one molecule of PX3 can convert 3 molecules of alcohol to the corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
Conversion using Thionyl Chloride (SOCl2) - Correct Answer Alcohol (R-OH) + Thionyl Chloride (Cl-S=O-Cl) —> alkyl
Chloride (R-Cl) + SO2 ^ + HCl
- very efficient with primary and secondary alcohols d/t the main byproduct (SO2) beig formed as a gas and leaving
the reaction mixture.
Crown Ethers - Correct Answer Can solvate cations within theur interior cavity, size of the ring controls which cations
can fit into the cavity, this allows ionic compounds to be dissolved in relatively non-polar organic solvents
Dehydration - Correct Answer Loss of water. An alcohol molecule will lose H2O to form an ALKENE. Type of
elimination reaction — lose the -OH from one C and H atom from the adjacent C.
First step — alcohol acts as a base.
Tertiary alcohols - E1
Primary alcohols - E2
