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Questions and Answers
What is the melting point of geraniol derivative?
What is the melting point of geraniol derivative?
Which of the following statements about citronellol is true?
Which of the following statements about citronellol is true?
Which product is known to contain nerol?
Which product is known to contain nerol?
What characteristic do geraniol and nerol share?
What characteristic do geraniol and nerol share?
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What odor is commonly associated with citronellol?
What odor is commonly associated with citronellol?
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What is a primary use of Linalol?
What is a primary use of Linalol?
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Which of the following is the most common isomer of Menthol?
Which of the following is the most common isomer of Menthol?
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What percentage of Menthol is typically found in oil of Japanese mint?
What percentage of Menthol is typically found in oil of Japanese mint?
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Which method is primarily used for isolating Menthol from Japanese mint oil?
Which method is primarily used for isolating Menthol from Japanese mint oil?
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What centers of asymmetry does Menthol have?
What centers of asymmetry does Menthol have?
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Which compound can be used for the semi-synthesis of dl-menthol?
Which compound can be used for the semi-synthesis of dl-menthol?
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Which method causes the deposition of menthol crystals during isolation?
Which method causes the deposition of menthol crystals during isolation?
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What reaction is associated with converting Thymol to Menthol?
What reaction is associated with converting Thymol to Menthol?
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Which type of alcohol is classified as primary?
Which type of alcohol is classified as primary?
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What classification method is used for alcohols based on their carbon skeleton?
What classification method is used for alcohols based on their carbon skeleton?
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Which of the following is an example of a monocyclic alicyclic alcohol?
Which of the following is an example of a monocyclic alicyclic alcohol?
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What type of alcohol is Nerolidol classified as?
What type of alcohol is Nerolidol classified as?
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Which of the following is NOT a saturated aliphatic alcohol?
Which of the following is NOT a saturated aliphatic alcohol?
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Which aromatic alcohol is characterized by a benzene ring with an alcohol group?
Which aromatic alcohol is characterized by a benzene ring with an alcohol group?
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What method is typically used for the isolation of alcohols from volatile oils?
What method is typically used for the isolation of alcohols from volatile oils?
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Which of the following statements regarding alcohol classification is accurate?
Which of the following statements regarding alcohol classification is accurate?
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Which type of alcohol is most reactive in dehydration reactions?
Which type of alcohol is most reactive in dehydration reactions?
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What is the primary purpose of esterification in the context of alcohols?
What is the primary purpose of esterification in the context of alcohols?
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What reaction occurs with primary alcohols when treated with anhydrous calcium chloride?
What reaction occurs with primary alcohols when treated with anhydrous calcium chloride?
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Which type of ester does not react with tertiary alcohols?
Which type of ester does not react with tertiary alcohols?
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In fractional distillation under reduced pressure, which property of the liquid is primarily utilized?
In fractional distillation under reduced pressure, which property of the liquid is primarily utilized?
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Which type of reaction occurs when a primary alcohol is hydrated?
Which type of reaction occurs when a primary alcohol is hydrated?
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What happens to secondary alcohols under more drastic dehydration conditions?
What happens to secondary alcohols under more drastic dehydration conditions?
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Which of the following statements is true regarding the reactivity of alcohols in the context of phthalic acid esters?
Which of the following statements is true regarding the reactivity of alcohols in the context of phthalic acid esters?
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What is one of the pharmacological actions of menthol?
What is one of the pharmacological actions of menthol?
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Which compound is primarily associated with a camphor-like odor?
Which compound is primarily associated with a camphor-like odor?
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What is the main constituent of pine needle oils derived from borneol?
What is the main constituent of pine needle oils derived from borneol?
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How is isoborneol classified in relation to borneol?
How is isoborneol classified in relation to borneol?
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Which method is used to isolate borneol from pine needle oil?
Which method is used to isolate borneol from pine needle oil?
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What chemical reaction is used to obtain borneol from α-pinene?
What chemical reaction is used to obtain borneol from α-pinene?
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What is the primary odor profile associated with α-terpineol?
What is the primary odor profile associated with α-terpineol?
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Which property of menthol contributes to its use in personal care products like mouthwashes and toothpastes?
Which property of menthol contributes to its use in personal care products like mouthwashes and toothpastes?
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What happens to 3ry alcohols under the specified reaction conditions?
What happens to 3ry alcohols under the specified reaction conditions?
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Which of the following methods can be used to extract acid phthalates?
Which of the following methods can be used to extract acid phthalates?
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Which alcohol type is quantitatively determined using the described processes?
Which alcohol type is quantitatively determined using the described processes?
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What type of compounds are formed from the reaction of carbamic acid with primary and secondary alcohols?
What type of compounds are formed from the reaction of carbamic acid with primary and secondary alcohols?
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Which reaction can separate primary alcohols from secondary and tertiary alcohols?
Which reaction can separate primary alcohols from secondary and tertiary alcohols?
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What is indicated by the formation of diphenyl urethane derivatives in the context of geraniol and nerol?
What is indicated by the formation of diphenyl urethane derivatives in the context of geraniol and nerol?
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Which of the following statements about secondary alcohols is true?
Which of the following statements about secondary alcohols is true?
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How can the hydrolysis of acid phthalates be achieved?
How can the hydrolysis of acid phthalates be achieved?
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Study Notes
Oxygenated Compounds
- Phytochemistry Lecture 4 covers oxygenated compounds, including alcohols, phenols, aldehydes, ketones, esters, oxides, and peroxides.
Alcohols in Volatile Oils
- Alcohols in volatile oils are frequently found with their esters.
- They are typically terpenoid or aromatic in nature.
- Classification:
- Based on the alcoholic group type: Primary (RCH₂OH), Secondary (R₂CHOH), and Tertiary (R₃COH).
- Based on the carbon skeleton: Aliphatic (acyclic), Alicyclic, and Aromatic.
- Further categorized into saturated, unsaturated, monoterpenoid, sesquiterpenoid, and aromatic alcohols. Specific examples of each type are included in the slides.
Isolation of Alcohols in Volatile Oils
- Methods of isolation: Fractional distillation under reduced pressure, Chromatography (CC, HPLC, GLC), Counter Current Extraction, Formation of crystalline derivatives (derivatization).
Reactions of Alcohols in Volatile Oils
-
Derivatization of Terpenoid Alcohols:
- Reactions similar to those of terpenoid hydrocarbons: Addition reactions (hydration, hydrogenation, halogenation).
- Reactions due to the presence of the alcoholic groups: Reactivity varies by alcohol type (1°, 2°, or 3°).
- The formed derivatives often have definite melting points used for identification or quantitative determination.
-
Dehydration Reactions: Used for 3° alcohols. 2° alcohols require harsher conditions; 1° alcohols generally do not readily dehydrate. Geraniol is an exception.
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Calcium Chloride Additive Compounds: Used to separate 1° alcohols (e.g., geraniol) from other alcohols by forming crystalline salts.
-
Esterification:
- Reaction speeds depend on the type of alcohol (1°, 2°, or 3°).
- Borates, acid phthalates, and urethans (carbamates) are common esters.
- Used to separate 1° and 2° alcohols from 3° alcohols.
- Specific ester types, such as benzoates, react with specific alcohol types (1° and 2°).
-
Phthalic Acid Esters (Phthalates): These esters are used to identify and separate primary and secondary alcohols from tertiary ones by forming water soluble salts, and under differing conditions.
-
Carbamic Acid Esters (Carbamates/Urethanes): Used for identifying 1° and 2° alcohols. Specific derivatives have distinct melting points enabling identification.
Acyclic Terpenoid Alcohols
-
Citronellol:
- Source: Oil of citronella, geranium, and rose.
- Properties: Optically active liquid with a rose-like odor.
- Uses: Perfume, cosmetics, soaps, rose oil substitute, insecticide.
-
Geraniol & Nerol:
- Source: Geranium, oils of neroli, and other oils.
- Properties: Optically inactive liquids with a rose-like odor.
- Reactions: Reactive under certain conditions (degradation), used in preparing derivatives for identification and separation.
- Uses: Perfume, cosmetics, flavorings, and oil substitutes.
-
Linalool:
- Source: Oils of lavender, bergamot, coriander, nutmeg.
- Properties: Optically active liquid with a lavender-like odor, highly unstable.
- Reactions: Easily dehydrates to monoterpene hydrocarbons. Often oxidized.
- Uses: Perfume, cosmetics, oils substitutes, in flavorings.
Alicyclic Terpenoid Alcohols
-
(-)-Menthol:
- Source: Oils of peppermint and Japanese mint.
- Properties: Crystalline, has a mint-like odor and a cooling taste, optical isomers.
- Isolation: Isolated by cooling Japanese mint oil.
- Semi-synthesis: Can be created through enzymatic or catalytic reduction.
- Reactions: Shows various reactions, including oxidation, dehydrogenation, and dehydration.
- Uses: Flavoring agent, topical anesthetic (cough drops, etc.).
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a-Terpineol:(detailed properties and uses exist in other sections)
- Source: Neroli, pine, camphor tree, and cajuput oil.
- Types: Different forms depending on the source.
- Isolation: Fractional distillation and acid phthalate preparation.
- Uses: Perfume, soaps, flavorings.
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Borneol & Isoborneol:
- Source: Pine needle oils.
- Borneol: Natural, useful for perfumes, and other preparations.
- Isoborneol: Artifact, unstable in harsher conditions, but important in the separation process.
- Isolation: Fractional distillation from pine needle oil, sometimes use acid phthalates.
Aromatic Alcohols
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Benzyl Alcohol:
- Source: Balsam Peru, balsam Tolu, and storax oils, and in jasmine oil.
- Properties: Used as a fixative in perfume.
- Reactions: Forms esters used in perfumery.
-
Phenyl Ethyl Alcohol:
- Source: Rose, Neroli.
- Properties: Rose-like odor used in perfumes, and flavors, and other related products.
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Description
This quiz covers Oxygenated Compounds discussed in Phytochemistry Lecture 4, focusing on alcohols, phenols, aldehydes, and more. Learn about the classification, isolation methods, and reactions of alcohols in volatile oils.