org chem p8

C. Amine

Which of the following functional groups is the most basic?

A. Imide C. Amine

B. Amide D. Aniline

C. Aniline derivative

Paracetamol chemically is a/an

A. Salicylate derivative

B. Azocaine derivative

C. Aniline derivative

D. Pyrazolone derivative

C. Indole

The following structure is the side chain of amino acid tryptophan. What is the name of the following structure?

A. Purine  C. Indole

B. Pyrimidine  D. Quinoline

D. I, II, III, IV

Aromatic Phenothiazine derivatives

I. Chlorpromazine  III. Triflupromazine

II. Promazine  IV. Prochlorperazine

A. I only  C. I, II, III

B. I, II  D. I, II, III, IV

A. Thioridazine

Phenothiazine derivative
A. Thioridazine  C. Hydroxyzine
B. Chlorprothixene  D. Molindone

A. Chlorpromazine

An aliphatic phenothiazine derivative

A. Chlorpromazine  C. Fluphenazine

B. Thiorizadine  D. Perphenazine

A. I, II, IV, VIII

Which of the listed phytopharmaceuticals are classified as alkaloids?

I. Atropine  V. Gingerol

II. Colchicine  VI. Eugenol

III. Curcumin  VII. Hesperidin

IV. Digoxin  VIII. Quinine

A. I, II, IV, VIII  C. III, IV, V, VIII

B. I, IV, VII, VIII  D. I, III, V, VII

A. Atropine

Which of the following is identified by the Vitali-Morris (Vitali-Morin) reaction whereby a violet coloration is observed when the residue of the unknown is treated with a drop of freshly prepared potassium hydroxide solution?

A. Atropine  C. Hesperidin

B. Quinine  D. Digoxin

A. Quinine

Which of the following is identified by the Thalleoquin test?

A. Quinine C. Digoxin

B. Atropine D. Hesperidin

D. Phenyl-ethylamine

Mescaline is a/an _____ derivative.

A. Steroid  C. Indole-ethylamine

B. Xanthine  D. Phenyl-ethylamine

B. May be dissolved in water by addition of a small amount of sulphuric acid to convert it to more soluble bisulfate

Which is True to the alkaloid quinine sulphate?

A. Has a sweet and pleasant taste.

B. May be dissolved in water by addition of a small amount of sulphuric acid to convert it to more soluble bisulfate

C. This alkaloid is poorly absorbed from the gastrointestinal tract

D. Is not damaged by exposure to light

Amides

General Formula → RCONH2

Properties of Amides

Cyclic amides → LACTAM

Based on the pic

• 1 is Beta Lactam

• 2 is Gamma lactam

• 3 is Delta Lactam

Properties of Amides

Susceptible to hydrolysis

• Amides undergo hydrolysis because the carbonyl carbon is reactive and gets attacked by nucleophiles, breaking the bond and forming CARBOXYLIC ACID + AMINE products.

Nomenclature of Amides

Common name: Common prefix + amine

IUPAC name: Alkan + amide

Cyclic ring: USE GREEK PREFIX + LACTAM

Acetamide

IUPAC Name → Ethanamide

Beta Lactam

Gamma Lactam

Lidocaine

Amide Local Anesthetics

• Remember that that if there are two i in its name it is amide local anesthetics

Bupivacaine

Amide Local Anesthetics

Dibucaine

Amide Local Anesthetics

C. Amide

Functional group of the beta-lactam ring

A. Ether  C. Amide

B. Ketone  D. Carbonyl

SULFUR-CONTAINING COMPOUNDS

• Thiols - RSH

• Thioethers - RSR

• Thioesters - RCOSR/RCSOR

Thiols

General Formula → R—SH

Nomenclature of Thiols

Common name: Alkyl + Mercaptan

IUPAC name: Alkane + thiol

Methylmercaptan

IUPAC Name → Methanethiol

Propylmercaptan

IUPAC Name →Propane-1-thiol

BAL - British Anti Lewisite

AKA: Dimercaprol

IUPAC Name → 2,3-dimercapto-1-propanol

Thioethers

General Formula → R—S—R'

Nomenclature of thioethers

Common name: Alkyl + sulfide

IUPAC nane: Alkylthio + Alkane

Methyl propyl sulfide

IUPAC Name → Methylthiopropane

• Propane - 3-carbon straight chain (CH3CH2CH2–)

• Methylthio - (–SCH₃) A methyl group connected through sulfur

Diethyl sulfide

IUPAC Name → Ethylthioethane

Thioesters

General Formula → RCOSR' or RCSOR

Nomenclature of thioesters

Common name: Alkyl + thio prefix -ate

IUPAC name: Alkyl + Alkane -thioate

Methylthioacetate

IUPAC Name → methylethanethioate

Benzylsulfanylurea

Example: Tolbutamide

Use: Oral hypoglycemic agent

Sulfamate

Example: Topiramate

• Sulfamate-substituted monosaccharide

• Derived from D-fructose

Use: ANTI EPILEPTIC agent

D. A and B

BAL is

A. British Anti-Lewisite

B. 2,3–dimercaptopropanol

C. 3,2–dimercaptopropanol

D. A and B

C. Oral hypoglycemics

Derivatives of benzylsulfonyl urea are useful as

A. Spasmolytics

B. Anti-inflammatory

C. Oral hypoglycemics

D. Diuretics

A. Topiramate

Sulfamate-substituted monosaccharide (related to fructose)

A. Topiramate

B. Valproic acid

C. Lamotrigine

D. Carbamazepine

HALOGEN-CONTAINING COMPOUNDS

• Alkyl halides - R-X

• Aryl halides - Ar-X

• Acyl halides - RCOX

Alkyl Halides

General Formula → R—X (X = F, Cl, Br, I)

Nomenclature of Alkyl Halides

IUPAC name: Halogen prefix + alkane

2-bromopropane

IUPAC Name →

Dichlorofluoromethane

IUPAC Name →

AKA FREON R-21

Chlorodifluoromethane

IUPAC Name →

AKA FREON R-22

Aryl Halides

→ General Formula: Ar-X

Nomenclature of Aryl Halides

IUPAC name: Halogen prefix + Aromatic Hydrocarbon

Acyl Halides

→ General Formula: RCOX

Nomenclature of Acyl Halides

IUPAC name: IUPAC prefix + oyl + halogen (-ide)

Easier way: Alkan + oyl halide

Aryl Halides

→ IUPAC Name: BROMOBENZENE

→ IUPAC Name: FLUOROBENZENE

→ IUPAC Name: 2,4-DICHLOROMETHYLBENZENE

Acyl Halides

→ IUPAC Name: Ethanoylchloride

D. Dichlorofluoromethane

Freon

A. Dichloromethane

B. Difluoroethane

C. Dibromomethane

D. Dichlorofluoromethane

C. Acid Halide

Functional group present in CH₃COCl

A. Alcohol

B. Aldehyde

C. Acid Halide

D. Ketone

ISOMERISM

→ Same MOLECULAR FORMULA, different STRUCTURE

true

ISOMER has two types:

• CONSTITUTIONAL

• STEREOISOMER

---

CONSTITUTIONAL:

• Chain

• Positional

• Functional

---

STEREOISOMER: divided into TWO

• CONFORMATIONAL

  • Ring conformers

  • Rotamers

• CONFIGURATIONAL

  • Geometric

  • Optical

CONSTITUTIONAL / STRUCTURAL ISOMERS

→ Compounds with:

• SAME molecular formula

• DIFFERENT structure

• DIFFERENT connectivity

Chain/Skeletal

Same:

• Molecular Formula

---

Different:

• Structure

• Parent name

• Branching

Positional

Same:

• Molecular Formula

• Parent name

---

Different:

• Structure

• Position

Functional

Same:

• Molecular Formula

---

Different:

• Structure

• Functional group

Pentane

CHAIN / SKELETAL ISOMERS

• Molecular Formula: C5H12

2-methylbutane

CHAIN / SKELETAL ISOMERS

• Molecular Formula: C5H12

2,2-dimethylpropane

CHAIN / SKELETAL ISOMERS

• Molecular Formula: C5H12

true

these are chain isomers

1-bromopropane

POSITIONAL ISOMERS

• Molecular Formula: C3H7Br

2-bromopropane

POSITIONAL ISOMERS

• Molecular Formula: C3H7Br

true

these are positional isomers

Benzene-1,2-diol

POSITIONAL ISOMERS

• Molecular Formula: C6H6O2

Benzene-1,3-diol

POSITIONAL ISOMERS

• Molecular Formula: C6H6O2

Benzene-1,4-diol

POSITIONAL ISOMERS

• Molecular Formula: C6H6O2

true

these are all positional isomers

Functional Isomers Example

✓ Same Molecular Formula: C2H6O

✓ Different structure and functional group: Ethanol and Dimethyl ether

FUNCTIONAL ISOMERS (Tautomers)

“facile interconversion” - effortless interconversion

• Tautomerism - Rapid shifting between 2 isomeric forms

• Facile interconversion - The switch happens easily and quickly

Propanone (acetone) - ketone form

1-propen-1-ol - enol form

C. 2-propanol

Which of the following can be considered as an isomer of n-propanol?

A. Acetone

B. Methoxymethane

C. 2-propanol

D. B and C

B. Positional isomers

2-pentanol and 3-pentanol are:

A. Functional isomers

B. Positional isomers

C. Chain isomers

D. Optical isomers

D. Tautomers

Propanone and 1-propen-1-ol are considered as:

A. Positional isomers

B. Configurational isomers

C. Chain isomers

D. Tautomers

D. Both A and B

A compound with a molecular formula of C₂H₆O is most likely to be a/an ______.

A. Alcohol

B. Ether

C. Ketone

D. Both A and B

STEREOISOMERS

→ Compounds with:

• SAME molecular formula

• DIFFERENT structure

• SAME order of atoms and connectivity

• DIFFRENT arrangement of atoms in space (configuration)

Conformational

Can be interconverted just by rotations ("TEMPORARY DIFFERENCE")

Ex.

• Ring conformers

• Rotamers

Configurational

Can be interconverted only by breaking bonds ("PERMANENT DIFFERENCE")

Ex.

• Geometric

• Optical

A. I, III

Which statements best characterize stereoisomers?

I. They do not differ in the order of their atoms.

II. They differ in the order and kind of atoms.

III. They differ in the spatial arrangement of their atoms.

IV. They do not differ in their configuration.

A. I, III

B. III,IV

C. II,III

D. I,IV