Functional Group Chemistry
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Questions and Answers

Understanding functional groups is essential for deducing the properties of drugs.

True

What are curly arrows used to denote in chemical reactions?

Bond making and breaking processes

In functional group chemistry, a substance that donates electrons is known as a _____ and one that accepts electrons is known as a _____ .

nucleophile; electrophile

Match the following terms with their definitions:

<p>Nucleophile = A species that donates electrons Electrophile = A species that accepts electrons Leaving group = The atom or group that departs with a pair of electrons Hyperconjugation = Stabilization by the overlap of electrons in adjacent sigma bonds</p> Signup and view all the answers

What characterizes an electrophile?

<p>Electron-loving and electron-poor</p> Signup and view all the answers

A nucleophile is characterized by having a positive charge.

<p>False</p> Signup and view all the answers

What is a leaving group?

<p>An ion or neutral molecule that is displaced from a reactant during a reaction.</p> Signup and view all the answers

Electrophiles are typically __________ charged particles.

<p>positively</p> Signup and view all the answers

Which of the following is NOT a characteristic of a good leaving group?

<p>Forms unstable ions or neutral molecules after departure</p> Signup and view all the answers

A reaction involving a nucleophile and an electrophile generally results in the formation of a __________.

<p>new product</p> Signup and view all the answers

What does a single-headed arrow represent in radical mechanisms?

<p>Movement of one electron</p> Signup and view all the answers

Double bonds in alkenes can act as strong electrophiles.

<p>False</p> Signup and view all the answers

The activation energy is defined as the energy difference between the starting material and the final products.

<p>False</p> Signup and view all the answers

What is formed when two radicals each donate one electron?

<p>A bond</p> Signup and view all the answers

The energy difference between reactants and products is known as the ________ change.

<p>standard free energy</p> Signup and view all the answers

In a radical mechanism, what is required to break a bond?

<p>One electron from each atom</p> Signup and view all the answers

Radicals always have a negative charge.

<p>False</p> Signup and view all the answers

What signifies an empty p orbital in the context of a polarised bond?

<p>Poor Centre</p> Signup and view all the answers

Which of the following statements about resonance structures is true?

<p>They involve delocalization of electron density.</p> Signup and view all the answers

Resonance forms can have different numbers of paired and unpaired electrons.

<p>False</p> Signup and view all the answers

What type of electrons are moved in resonance structures?

<p>π electrons and lone-pair electrons.</p> Signup and view all the answers

The _______ represents the extreme possibilities of electron location in resonance structures.

<p>resonance forms</p> Signup and view all the answers

Which of the following is NOT a characteristic of resonance structures?

<p>They can change the positions of atoms.</p> Signup and view all the answers

Only sp3 hybridized atoms can participate in resonance.

<p>False</p> Signup and view all the answers

What do resonance structures help to understand in chemistry?

<p>Reaction mechanisms.</p> Signup and view all the answers

What is produced during the condensation process of ester formation?

<p>Water</p> Signup and view all the answers

Oxidation is the opposite of reduction.

<p>True</p> Signup and view all the answers

What role does NAD+ play in the biological oxidation of alcohols?

<p>Coenzyme</p> Signup and view all the answers

The process of converting an alcohol to an aldehyde is facilitated by the enzyme _____ .

<p>alcohol dehydrogenase</p> Signup and view all the answers

Match the following components of ester formation with their descriptions:

<p>Fischer Esterification = A classical transformation for ester formation H2SO4 = Source of H+ and dehydrating agent Le Chatelier's Principle = Used to shift equilibrium towards product Aqueous acid hydrolysis = Converts esters to carboxylic acids</p> Signup and view all the answers

Which has the capability of converting a hydroxyl group to a halogen?

<p>Addition of H-X</p> Signup and view all the answers

Disulfiram can inhibit the conversion of aldehyde to acid.

<p>True</p> Signup and view all the answers

What type of reaction is involved in the formation of an alkyl halide?

<p>Nucleophilic substitution</p> Signup and view all the answers

The first step in biological oxidation converts alcohol to an ____________ .

<p>aldehyde</p> Signup and view all the answers

What is a consequence of the condensation process in ester formation when water is produced?

<p>Reaction shifts to the right</p> Signup and view all the answers

What is the primary functional group in alcohols?

<p>Hydroxyl</p> Signup and view all the answers

Phenols are less acidic than cyclohexanol.

<p>False</p> Signup and view all the answers

What effect do halogens have on the acidity of alcohols?

<p>Halogens increase acidity.</p> Signup and view all the answers

The pKa of phenol is approximately _____ compared to alcohols like cyclohexanol.

<p>10</p> Signup and view all the answers

Match the alcohol to its boiling point trend:

<p>Methanol = Lowest boiling point Ethanol = Lower boiling point than isopropyl alcohol Isopropyl alcohol = Higher boiling point than ethanol t-Butyl alcohol = Highest boiling point among small alcohols</p> Signup and view all the answers

Which of the following factors decreases the acidity of alcohols?

<p>Increased alkyl substitution</p> Signup and view all the answers

Alcohols can participate in nucleophilic substitution reactions.

<p>True</p> Signup and view all the answers

Describe how solubility of small alcohols in water changes as the size of the alkyl group increases.

<p>Solubility decreases.</p> Signup and view all the answers

The reaction of alkenes with water to form alcohols is known as __________.

<p>hydration</p> Signup and view all the answers

Match the alcohol with its preparation method:

<p>Methanol = Direct synthesis from CO and H2 Ethanol = Fermentation of starch and grains Isopropyl alcohol = Hydration of propylene 2-Chloroethanol = Hydrolysis of alkyl halides</p> Signup and view all the answers

Which alcohol has the highest pKa value?

<p>t-Butyl alcohol</p> Signup and view all the answers

The boiling points of alcohols are generally low due to weak intermolecular forces.

<p>False</p> Signup and view all the answers

What is the common pKa range for alcohols?

<p>15.5 to 18.0</p> Signup and view all the answers

Alcohols are classified as __________ compounds based on their structure.

<p>saturated or unsaturated</p> Signup and view all the answers

Match the description with the correct type of alcohol:

<p>Methanol = Simple alcohol usually toxic Ethanol = Commonly used in beverages Isopropyl alcohol = Used as a disinfectant t-Butyl alcohol = Highly branched alcohol</p> Signup and view all the answers

What characteristic do molecules with the same functional group generally possess?

<p>Similar properties and characteristic reactivities</p> Signup and view all the answers

In drug design, which aspect is primarily affected by the physiochemical properties of a substance?

<p>Therapeutic effectiveness and rapid absorption</p> Signup and view all the answers

Which of the following statements best defines a functional group in organic molecules?

<p>The reactive part of the molecule where most interactions occur</p> Signup and view all the answers

How do hydrocarbon parts of drugs typically contribute to their properties?

<p>They provide unreactive support and influence solubility</p> Signup and view all the answers

What is the significance of receptor binding in pharmacology?

<p>It produces the therapeutic effect of the drug.</p> Signup and view all the answers

What shape do sp3 hybridized carbon atoms adopt?

<p>Tetrahedral</p> Signup and view all the answers

Which bond representation indicates a bond pointing towards the observer?

<p>Wedge</p> Signup and view all the answers

What type of reaction mechanism involves the movement of one electron at a time?

<p>Radical</p> Signup and view all the answers

In reactivity and reaction mechanisms, what primarily describes the formation of products from reactants?

<p>Bond-making and bond-breaking steps</p> Signup and view all the answers

What characterizes a nucleophile?

<p>Electron-rich species</p> Signup and view all the answers

How is a chiral center defined in terms of carbon atoms?

<p>Carbon with four different groups attached</p> Signup and view all the answers

Which representation indicates that a bond is in the plane of the screen?

<p>Plain bond</p> Signup and view all the answers

What distinguishes radical mechanisms from other chemical mechanisms?

<p>Movement of single electrons</p> Signup and view all the answers

What type of addition occurs when alkenes react with halogens such as Cl2 or Br2?

<p>Anti addition</p> Signup and view all the answers

Which ion is formed when a bromine molecule interacts with an alkene during the cyclic bromonium ion formation?

<p>Bromonium ion</p> Signup and view all the answers

What stabilizes the product in a radical reaction involving bromine?

<p>Formation of the most stable carbon radical</p> Signup and view all the answers

What is the role of a catalyst in the hydrogenation of alkenes?

<p>To reduce the activation energy of the reaction</p> Signup and view all the answers

During the halogenation of alkenes, what is the stereospecificity of the reaction?

<p>Trans addition</p> Signup and view all the answers

In what way does the reactivity of an alkene change after hydrogenation?

<p>Decreases because it forms an alkane</p> Signup and view all the answers

What is the main product formed from the addition of bromine to an alkene?

<p>Vicinal dihalide</p> Signup and view all the answers

What characteristic defines the addition of halogens to alkenes as stereospecific?

<p>The addition results in a defined spatial arrangement of substituents</p> Signup and view all the answers

Which condition is essential for the hydrogenation of an alkene to occur?

<p>Use of a metal catalyst</p> Signup and view all the answers

What factor primarily determines the distribution patterns of products in free-radical substitution reactions?

<p>The stability of the intermediate radical</p> Signup and view all the answers

Which type of carbon radical is the most stable?

<p>Tertiary radical</p> Signup and view all the answers

How does hyperconjugation stabilize carbocations?

<p>Through electron sharing between σ-bonds and adjacent p-orbitals</p> Signup and view all the answers

Which of the following radicals is unusually stable due to resonance effects?

<p>Benzyl radical</p> Signup and view all the answers

In terms of the stability of radicals, which arrangement produces the most stable intermediate?

<p>A radical with three carbon atoms bonded to it</p> Signup and view all the answers

What role do alkyl groups play in the stability of radicals?

<p>They are weakly electron donating due to the hyperconjugation effect</p> Signup and view all the answers

Which of the following represents the least stable type of carbon radical?

<p>Primary radical</p> Signup and view all the answers

Which molecular feature is crucial for increasing the stability of a radical?

<p>The number of adjacent carbon atoms</p> Signup and view all the answers

What stabilizes benzyl and allyl radicals specifically?

<p>Resonance effects</p> Signup and view all the answers

Which of the following statements is true regarding radical stability?

<p>The stability of radicals can influence the pathway of reactions</p> Signup and view all the answers

What is the general formula for alkynes?

<p>CnH2n-2</p> Signup and view all the answers

Which factor determines the reactivity of alkynes?

<p>Electron rich C-C triple bonds</p> Signup and view all the answers

Which reaction type is commonly used during the alkylation of terminal alkynes?

<p>Nucleophilic substitution</p> Signup and view all the answers

Which of the following statements about alkyne acidity is true?

<p>The acidity of alkynes increases with the hybridization of carbon.</p> Signup and view all the answers

In comparison to alkenes, how do alkynes behave in terms of reactivity?

<p>Alkynes are less reactive than alkenes.</p> Signup and view all the answers

What is a characteristic of internal alkenes or alkynes in terms of boiling point?

<p>They have higher boiling points than terminal chains of equal mass.</p> Signup and view all the answers

Which addition reaction can alkynes undergo in excess reagent conditions?

<p>Hydrogenation</p> Signup and view all the answers

Which of the following pKa values represents a terminal alkyne?

<p>25</p> Signup and view all the answers

Which addition rule is followed by the reactions of alkynes?

<p>Markovnikov's Rule</p> Signup and view all the answers

Which statement correctly describes the stability of alkenes?

<p>More substituted alkenes are more stable due to hyperconjugation.</p> Signup and view all the answers

What type of bond is primarily responsible for the reactivity of alkenes?

<p>pi bond</p> Signup and view all the answers

Which statement accurately reflects the boiling points of alkenes compared to alkanes?

<p>Alkenes have lower boiling points that increase with molecular weight.</p> Signup and view all the answers

Which characteristic is true about cis and trans isomers of alkenes?

<p>Trans isomers are generally more stable than cis isomers.</p> Signup and view all the answers

Which of the following processes is NOT commonly associated with alkene reactivity?

<p>Thermal cracking</p> Signup and view all the answers

What does Markovnikov's rule predict in electrophilic addition reactions?

<p>Hydrogen will add to the more substituted carbon atom.</p> Signup and view all the answers

What type of interactions do alkenes exhibit due to their slightly polar nature?

<p>Instantaneous dipole-dipole interactions</p> Signup and view all the answers

Which of the following statements is true regarding the solubility of alkenes?

<p>Alkenes are virtually insoluble in water.</p> Signup and view all the answers

What is the effect of alkyl groups on the stability of alkenes?

<p>Alkyl groups stabilize alkenes by electron donation.</p> Signup and view all the answers

Study Notes

MPharm Programme PHA111 Functional Group Chemistry

  • This is a week 10 and week 11 course on functional group chemistry.
  • The lecturer is Dr. Stephanie Myers, Senior Lecturer in Medicinal Chemistry.
  • The course is for the MPharm Programme.
  • The course covers functional group chemistry, learning objectives, functional groups, chemical similarity, definitions of functional groups, chemical representations, reactivity and reaction mechanisms, nucleophiles, electrophiles, leaving groups, bond cleavage, curly arrows, polar and radical mechanisms, transition states and intermediates, reasons to study mechanisms, mechanisms of penicillins, hydrocarbon compounds, alkanes, physical properties of alkanes, reactivity of alkanes, halogenation of alkanes, radical stability, hyperconjugation, radical stability, resonance contributors and hybrids, resonance structures, resonance, resonance stability of radicals, oxidation of drugs, auto oxidation.
  • The course also covers functional group chemistry 2 and 3.
  • Additional topics include learning objectives, unsaturated compounds, alkenes, alkenes as isomers, alkenes in vision, alkenes reactivity, preparation, elimination, addition reactions, alkynes, alkynes structure, alkynes physical properties, alkynes reactivity, alkylation of terminal alkynes, alkynes addition of HX, alkynes properties, addition reactions, Markovnikov's rule, carbocation stability, hydration of alkenes, anti-Markovnikov addition, addition of halogens, hydrogenation of alkenes, hydrogenation of alkynes, versatile reagents, acid/base properties of amino acids, alcohols, preparation of alcohols, reduction of carbonyl compounds, reactivity of alcohols, ester formation (Fischer esterification), oxidation of alcohols, biological oxidation of alcohols, haloalkanes, haloalkanes as anaesthetics, haloalkanes physical properties, haloalkanes reactivity, SN1 and SN2 reactions, amines, amine occurrence, amine synthesis, reactions with carboxylic acid derivatives, amines structure and bonding, amine classification, amines hydrogen bonding, lone pairs of amines, and acid/base properties of amino acids (Zwitterions).

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