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Pharmchem > Heterocyclics > Flashcards

Heterocyclics Flashcards

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1
Q

What are carbonyl compounds?

A

Compounds having a carbonyl functional group (C=O)

Includes aldehydes, ketones, carboxylic acids, acid halides, acid anhydrides, esters, amides, lactones, and lactams.

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2
Q

What are the uses of aldehydes and ketones?

A

Used as solvents, synthesis of alcohols, insulation materials, adhesive resins, preservative of biological specimens

Example: Formaldehyde is used as an insulation material.

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3
Q

What is the biological importance of carboxylic acids?

A

Biological precursors of fats and lipids, found in compounds like cholic acid

Example: Vinegar is a dilute aqueous solution of acetic acid.

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4
Q

What causes the rancid odor of butter?

A

Presence of butanoic acid

This compound contributes to the unpleasant smell.

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5
Q

List the uses of esters.

A
  • Perfumery industry
  • Flavour enhancers in food
  • Cosmetics
  • Solvents for coatings, paints, and varnishes

Example: Dacron is a polyester used in textile manufacture.

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6
Q

What are acid halides used for?

A

Used to prepare carboxylic acids, esters, amides, and anhydrides.

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7
Q

What is the role of amines in organic chemistry?

A

Used for preparation of insecticides, pharmaceuticals, and neurotransmitters

Example: Propranolol is a heart stimulant made from amines.

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8
Q

What are the two main classifications of carbonyls?

A
  • Aldehydes
  • Ketones

Aldehydes have the acyl group (-C=O) joined to H, while ketones have it joined to R (alkyl or aromatic).

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9
Q

Describe the bonding in carbonyls.

A

C=O bond length of 1.21 A; bond is polar due to electronegativity of oxygen

The carbon develops a partial positive charge, making it an electrophilic site.

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10
Q

What types of reactions do carbonyl compounds undergo?

A
  • Nucleophilic addition
  • Nucleophilic acyl substitution
  • Alpha-substitution
  • Carbonyl condensation
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11
Q

How are aldehydes named in nomenclature?

A

The -e ending of the parent alkane name is replaced by the suffix -al

The carbonyl carbon is always numbered 1.

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12
Q

What is the boiling point trend for aldehydes and ketones?

A

Boiling points increase with the increase in molecular weights

They lack hydrogen bonding compared to alcohols and carboxylic acids.

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13
Q

Why are aldehydes more reactive than ketones?

A

Aldehydes have less steric hindrance and fewer electron-supplying groups than ketones.

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14
Q

Define organic acids.

A

Organic molecules characterized by a hydrogen atom that can be released as a proton.

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15
Q

What functional groups classify organic acids?

A
  • Carboxyl group (−COOH)
  • Sulfo group (−S(=O)2−OH)
  • Hydroxyl group (−OH)
  • Thiol group (−SH)
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16
Q

What is the significance of organic acids in food preservation?

A

They disrupt the normal physiology of bacteria that are pH-sensitive.

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17
Q

What are the steps in the nomenclature of carboxylic acids?

A
  • Select the longest carbon chain containing the carboxyl group
  • Replace the -e ending with -oic acid
  • Number the carboxyl carbon as 1
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18
Q

What are the physical properties of carboxylic acids?

A
  • Higher boiling points than other molecules of similar molecular weight
  • Generally liquids at room temperature with sharp smells
  • Short-chain acids are more soluble in water
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19
Q

How do carboxylic acids dissociate?

A

They ionize partially, releasing a small number of protons.

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20
Q

What is the general trend in solubility of carboxylic acids?

A

As the number of carbons increases, solubility in water decreases.

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21
Q

What is the difference between aromatic and aliphatic carboxylic acids?

A

Aromatic carboxylic acids, like benzoic acid, have resonance stabilization of the carboxylate anion.

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22
Q

How is benzoic acid more acidic than aliphatic organic acids?

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A

Due to resonance stabilization of the carboxylate anion

This resonance allows for greater delocalization of charge.

23
Q

What are the main reactions of benzoic acid?

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A

Similar to aliphatic organic acids, including:
* Reaction with NH3
* Anhydride formation
* Reaction with thionyl chloride
* Reaction with alcohols
* Decarboxylation
* Salt formation

These reactions showcase the versatility of benzoic acid in organic synthesis.

24
Q

What is the significance of esters in organic chemistry?

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A

They constitute the most important class of organic acid derivatives and are responsible for the fragrance of many fruits and flowers

Esters are widely used in flavorings and fragrances.

25
Name an ester found in apples.
Methyl butyrate ## Footnote Methyl butyrate is derived from methanol and butanoic acid.
26
How are esters named in IUPAC nomenclature?
Name the alkyl group of the alcohol first followed by the name of the carboxylic acid, replacing -ic in acid with -ate ## Footnote Example: HCOOCH3 is methyl methanoate.
27
What is the most versatile method for preparing esters?
Nucleophilic acyl substitution of an acid chloride with an alcohol ## Footnote This method allows for a wide variety of esters to be synthesized.
28
What are the main reactions of esters?
Esters can undergo: * Hydrolysis to form carboxylic acids * Alcoholysis to form different esters * Aminolysis to form amides * Reaction with Grignard reagents * Reaction with hydride reagents ## Footnote These reactions highlight the functional versatility of esters.
29
Define primary amines.
Derivatives of ammonia with one hydrogen atom replaced by an alkyl or aryl group ## Footnote Examples include methylamine and ethylamine.
30
What is the structure of secondary amines?
Derivatives of ammonia with two hydrogen atoms replaced by alkyl or aryl groups ## Footnote Examples include diethylamine and diphenylamine.
31
What characterizes tertiary amines?
All three hydrogen atoms of ammonia are replaced by alkyl or aryl groups ## Footnote Examples include trimethylamine and triethylamine.
32
How are primary amines named in IUPAC nomenclature?
Name the alkyl group bonded to the amino group and add the suffix '-amine' ## Footnote Example: CH3–NH2 is named methylamine.
33
What types of isomerism can occur in amines?
Four types: * Chain isomerism * Position isomerism * Functional isomerism * Metamerism ## Footnote Each type of isomerism arises from different structural arrangements of the same molecular formula.
34
What is ammonolysis in the context of amines?
The reaction between alkyl halides and ammonia to form amines ## Footnote It can yield primary, secondary, tertiary, and quaternary amines.
35
What is the boiling point trend among primary, secondary, and tertiary amines?
Primary amines > Secondary amines > Tertiary amines ## Footnote This trend is due to the ability of primary and secondary amines to form hydrogen bonds.
36
What is the basic character of amines?
Amines can form well-defined crystalline salts with acids ## Footnote Example: C2H5NH2 + HCl forms C2H5N+H3 + Cl-.
37
What are the physical properties of phenols?
Phenols are white crystalline solids, sparingly soluble in water, and have a pH of about 5 ## Footnote The acidity is due to the stabilization of the phenoxide ion.
38
What is the reaction of phenol with bromine?
Phenol reacts with bromine water, decolorizing it and forming 2,4,6-tribromophenol ## Footnote This is an example of electrophilic substitution.
39
How does the presence of electron-withdrawing groups affect the acidity of phenols?
It increases acidity by stabilizing the phenoxide ion ## Footnote Conversely, electron-releasing groups decrease acidity.
40
What is the order of acidity among various compounds?
RCOOH > H2CO3 > C6H5OH > H2O > R–OH ## Footnote This order reflects the strength of the acids based on their dissociation in water.
41
How are acid chlorides synthesized?
From carboxylic acids using reagents like SOCl2 ## Footnote Example: CH3COOH + SOCl2 → CH3COCl + SO2 + HCl.
42
What are acid chlorides?
Compounds that do not occur in nature but are prepared in the laboratory ## Footnote Acid chlorides are derivatives of carboxylic acids and are characterized by the presence of a chlorine atom attached to the carbonyl carbon.
43
What is the nomenclature for CH3COCl?
Ethanoyl chloride or acetyl chloride ## Footnote This compound is commonly used in organic synthesis.
44
What is the nomenclature for CH3CH2CH2COBr?
Butanoyl bromide ## Footnote It is a type of acid halide used in various chemical reactions.
45
What is the nomenclature for CH3CH2COCl?
Propanoyl chloride ## Footnote Propanoyl chloride is used in the synthesis of other organic compounds.
46
What is the synthesis reaction for ethanoyl chloride using sulfur dichloride?
CH3COOH + SOCl2 → CH3COCl + SO2 + HCl ## Footnote This reaction illustrates the conversion of acetic acid to ethanoyl chloride.
47
What is the synthesis reaction for ethanoyl chloride using phosphorus pentachloride?
CH3COOH + PCl5 → CH3COCl + POCl3 + HCl ## Footnote Phosphorus pentachloride is another common reagent used in the formation of acid chlorides.
48
What are acid anhydrides?
Formed by the removal of water from two molecules of a carboxylic acid ## Footnote Acid anhydrides can be used to create esters and amides.
49
What is the nomenclature for (CH3CO)2O?
Acetic anhydride or ethanoic anhydride ## Footnote Acetic anhydride is widely used in chemical synthesis and acetylation reactions.
50
What is the nomenclature for (C6H5CO)2O?
Benzoic anhydride ## Footnote Benzoic anhydride is used in organic synthesis as a reagent.
51
What is the synthesis reaction for acetic anhydride using sodium acetate and ethanoyl chloride?
CH3COONa + CH3COCl → (CH3CO)2O + NaCl ## Footnote This reaction shows the formation of acetic anhydride from sodium acetate and ethanoyl chloride.
52
What is the synthesis reaction for acetic anhydride using acetic acid and phosphorus pentoxide?
2CH3COOH + P2O5 → (CH3CO)2O + H2O ## Footnote Phosphorus pentoxide acts as a dehydrating agent in this reaction.
53
What is the synthesis reaction for succinic anhydride using a specific compound and phosphorus pentoxide?
OHCO2CH2CH2COOH + P2O5 → Succinic anhydride ## Footnote This reaction highlights the formation of succinic anhydride from a dicarboxylic acid.

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