Topic 18: Organic Chemistry III Flashcards

Explain the chemistry of aromatic compounds, amines, polymers, and biological molecules including proteins and DNA. (155 cards)

1
Q

What type of hydrocarbon is benzene classified as?

A

Aromatic hydrocarbon

Aromatic compounds contain a benzene ring with delocalised electrons.

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2
Q

What is the shape of the benzene molecule?

A

Planar hexagon

All carbon atoms lie in the same plane with bond angles of about 120°.

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3
Q

Fill in the blank:

In benzene, all carbon–carbon bond lengths are _______ between single and double bonds.

A

intermediate

The bonds are all the same length due to electron delocalisation.

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4
Q

True or False:

Benzene contains alternating single and double bonds that remain fixed in position.

A

False

The π electrons are delocalised around the ring.

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5
Q

What type of electrons are delocalised in the benzene ring?

A

p electrons

These electrons form a delocalised π system above and below the ring.

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6
Q

True or False:

Delocalisation of electrons increases the stability of benzene.

A

True

Delocalisation lowers the overall energy of the molecule.

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7
Q

Fill in the blank:

The hypothetical molecule with alternating double bonds used for comparison with benzene is ______-______.

A

cyclohexa-1,3,5-triene

Benzene is more stable than this theoretical structure.

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8
Q

What thermochemical measurement provides evidence for benzene’s extra stability?

A

Enthalpy of hydrogenation

Benzene releases less energy than expected when hydrogenated.

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9
Q

True or False:

Benzene undergoes addition reactions easily like alkenes.

A

False

Addition would break the delocalised electron system.

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10
Q

Fill in the blank:

Benzene usually reacts by _______ reactions rather than addition reactions.

A

substitution

Substitution preserves the aromatic ring.

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11
Q

Why are substitution reactions preferred over addition reactions in benzene?

A

Preserve delocalisation

Addition would destroy the stable aromatic system.

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12
Q

What feature of benzene bonding explains its unusual stability?

A

Electron delocalisation

The π electrons are spread evenly over the entire ring.

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13
Q

What type of reaction commonly occurs when benzene reacts with electrophiles?

A

Electrophilic substitution

A hydrogen atom on the benzene ring is replaced by another group.

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14
Q

Why does benzene prefer substitution reactions rather than addition reactions?

A

Preserve aromatic stability

Addition would disrupt the delocalised π electron system.

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15
Q

Fill in the blank:

In electrophilic substitution, the benzene ring acts as a source of _______.

A

electrons

The π electron cloud attacks the electrophile.

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16
Q

True or False:

Electrophiles are electron pair acceptors.

A

True

They are attracted to regions of high electron density.

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17
Q

What reaction introduces a nitro group into a benzene ring?

A

Nitration

This reaction forms nitrobenzene.

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18
Q

True or False:

Nitration of benzene requires a mixture of concentrated nitric and sulfuric acids.

A

True

Sulfuric acid acts as a catalyst and generates the nitronium ion electrophile.

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19
Q

Fill in the blank:

The electrophile in benzene nitration is the _______ ion.

A

nitronium

The ion has the formula NO2+.

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20
Q

What role does concentrated sulfuric acid play in nitration?

A

Catalyst

It helps generate the nitronium ion from nitric acid.

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21
Q

True or False:

Friedel–Crafts acylation introduces an acyl group onto a benzene ring.

A

True

The reaction forms a ketone attached to the ring.

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22
Q

Fill in the blank:

In Friedel–Crafts acylation, the catalyst commonly used is _______.

A

AlCl3

Aluminium chloride helps generate the electrophile.

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23
Q

What type of compound is produced when benzene undergoes acylation?

A

Phenyl-ketone

The benzene ring becomes bonded to a carbonyl-containing group.

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24
Q

Why are nitration and acylation important in industrial chemistry?

A

Synthetic intermediates

They produce compounds used in explosives, dyes and pharmaceuticals.

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25
What is the **equation for the generation of the nitronium ion** from nitric acid?
HNO₃ + H₂SO₄ → NO₂⁺ + HSO₄⁻ + H₂O
26
What is the **equation for formation of the acylium ion**?
RCOCl + AlCl₃ → RCO⁺ + AlCl₄⁻
27
What happens to **AlCl₄⁻ after substitution**?
Reacts with H⁺ to regenerate AlCl₃ and form HCl
28
Why is **AlCl₃** considered a **catalyst**?
It is regenerated at the end of the reaction
29
How is **sulfuric acid regenerated** at the end of the nitration of benzene?
HSO₄⁻ + H⁺ → H₂SO₄ ## Footnote Reacts with the H+ released from the benzene ring.
30
What type of **organic compound** contains the functional group **–NH2**?
Primary Amine ## Footnote Amines are derivatives of ammonia where hydrogen atoms are replaced by alkyl or aryl groups.
31
What type of **amine** is formed when **ammonia reacts with a halogenoalkane**?
Primary amine ## Footnote The halogen atom is replaced by an –NH2 group.
32
# Fill in the blank: Reaction of a **halogenoalkane with ammonia** is an example of _\_\_\_\_\_\_ substitution.
nucleophilic ## Footnote Ammonia acts as a nucleophile donating a lone pair.
33
# True or False: **Nitriles** can be reduced to form **primary amines**.
True ## Footnote Reduction adds hydrogen across the C≡N bond.
34
What **functional group** must be reduced to convert a **nitrile into a primary amine**?
Nitrile group ## Footnote The –C≡N group is reduced to –CH2NH2.
35
# Fill in the blank: The **reduction of nitriles to amines** requires the addition of _\_\_\_\_\_\_.
hydrogen ## Footnote The triple bond is reduced to a single bond.
36
# True or False: **Aromatic amines** can be prepared by **reducing nitro compounds**.
True ## Footnote The nitro group (–NO2) is converted to an amine group (–NH2).
37
What type of **compounds** are **aromatic amines** commonly used to manufacture?
Dyes ## Footnote Many synthetic dyes are produced from aromatic amines.
38
# Fill in the blank: The **nitro group** in aromatic compounds is represented as _\_\_\_\_\_\_.
–NO2 ## Footnote Reduction converts it to –NH2.
39
What **reagent** is commonly used to **reduce nitro compounds to aromatic amines** in the laboratory?
Tin and hydrochloric acid ## Footnote The amine is then released by adding alkali.
40
# True or False: **Ammonia** acts as a **nucleophile when reacting with halogenoalkanes**.
True ## Footnote It donates a lone pair of electrons to the carbon atom.
41
Why are **aromatic amines** important in **industrial chemistry**?
Dye manufacture ## Footnote They are key intermediates in producing coloured compounds.
42
What type of **chemical behaviour** do amines exhibit in **aqueous solution**?
Weak bases ## Footnote Amines accept protons using the lone pair on the nitrogen atom.
43
What **particle** allows **amines to act as bases**?
Lone pair on nitrogen ## Footnote The lone pair can accept a proton (H+).
44
# Fill in the blank: **Amines** act as bases because the **nitrogen atom** has a _\_\_\_\_\_\_ pair of electrons.
lone ## Footnote This pair can bond with H+ to form an ammonium ion.
45
# True or False: **Amines** react with **acids to form ammonium salts**.
True ## Footnote The amine accepts a proton from the acid.
46
Which compound is generally the **weakest base**: ammonia, primary aliphatic amine, or primary aromatic amine?
Primary aromatic amine ## Footnote Delocalisation of the lone pair reduces its availability.
47
# True or False: Primary aliphatic amines are **stronger bases than ammonia**.
True ## Footnote Alkyl groups donate electron density to nitrogen.
48
# Fill in the blank: **Alkyl groups** increase the basic strength of amines by _\_\_\_\_\_\_ electron density to nitrogen.
donating ## Footnote This makes the lone pair more available to accept a proton.
49
Why are **aromatic amines** weaker bases than **aliphatic amines**?
Lone pair delocalisation ## Footnote The lone pair interacts with the benzene ring π system.
50
# True or False: In **aromatic amines**, the **nitrogen lone pair** is partially delocalised into the benzene ring.
True ## Footnote This reduces its ability to bond with H+.
51
# Fill in the blank: When an **amine accepts a proton**, it forms an _\_\_\_\_\_\_ ion.
ammonium ## Footnote The nitrogen atom gains a positive charge.
52
What factor mainly determines the **basic strength of amines**?
Availability of lone pair ## Footnote The more available the lone pair, the stronger the base.
53
Why do **primary aliphatic amines** act as stronger bases than **aromatic amines**?
Electron-donating alkyl groups ## Footnote Alkyl groups increase electron density on nitrogen.
54
Why are **amines** able to act as **nucleophiles in organic reactions**?
Lone pair on nitrogen ## Footnote The nitrogen atom can donate its lone pair to an electron-deficient carbon.
55
What type of **reaction** occurs when **ammonia reacts with a halogenoalkane**?
Nucleophilic substitution ## Footnote The nucleophile replaces the halogen atom in the molecule.
56
# Fill in the blank: In **nucleophilic substitution with halogenoalkanes**, ammonia acts as a _\_\_\_\_\_\_.
nucleophile ## Footnote It donates a pair of electrons to the carbon atom.
57
# True or False: **Ammonia reacting with a halogenoalkane** initially forms a **primary amine**.
True ## Footnote The halogen is replaced by an –NH2 group.
58
What **product** forms when a **primary amine reacts further with a halogenoalkane**?
Secondary amine ## Footnote The nitrogen becomes bonded to two alkyl groups.
59
# True or False: Reaction of **amines with halogenoalkanes** can lead to **quaternary ammonium salts**.
True ## Footnote Repeated substitution replaces all hydrogen atoms on nitrogen.
60
# Fill in the blank: A **nitrogen atom bonded to four alkyl groups** forms a _\_\_\_\_\_\_ ammonium ion.
quaternary ## Footnote These ions carry a permanent positive charge.
61
What **industrial application** commonly uses **quaternary ammonium salts**?
Cationic surfactants ## Footnote They are used in detergents, disinfectants and fabric softeners.
62
# True or False: **Ammonia** can react with **acyl chlorides to form amides**.
True ## Footnote The chlorine atom is replaced by an –NH2 group.
63
# Fill in the blank: The **reaction of ammonia with an acyl chloride** produces an _\_\_\_\_\_\_.
amide ## Footnote The product contains the –CONH2 functional group.
64
What type of **mechanism** occurs when **amines react with acyl chlorides**?
Nucleophilic addition–elimination ## Footnote The nucleophile adds to the carbonyl carbon then a leaving group is eliminated.
65
Why is the **carbonyl carbon in acyl chlorides** susceptible to **nucleophilic attack**?
Partial positive charge ## Footnote The electronegative oxygen withdraws electron density from the carbonyl carbon.
66
What **product** forms when a **secondary amine reacts further with a halogenoalkane**?
Tertiary amine
67
What **product** forms when a **tertiary amine reacts further with a halogenoalkane**?
Quaternary ammonium salt
68
What is the functional group of a **secondary amine**?
–NHR ## Footnote Two alkyl groups bonded to the nitrogen and one hydrogen bonded.
69
What is the functional group of a **tertiary amine**?
NR₂ ## Footnote Three alkyl groups attached to the nitrogen.
70
What is the functional group of a **quaternary ammonium salt**?
–NR₄⁺ ## Footnote Four alkyl or aryl groups attached to nitrogen, carrying a positive charge, usually paired with a counterion like Cl⁻.
71
What type of **polymer** forms when monomers join together with the **elimination of a small molecule**?
Condensation polymer ## Footnote Small molecules such as water or HCl are released during polymer formation.
72
What type of **monomers** react together to form **polyesters**?
Dicarboxylic acids and diols ## Footnote The reaction forms ester linkages between repeating units.
73
# Fill in the blank: The **linkage formed in polyesters** is called an _\_\_\_\_\_\_ linkage.
ester ## Footnote It has the functional group –COO–.
74
# True or False: **Polyamides** are formed by reactions between **dicarboxylic acids and diamines**.
True ## Footnote The reaction forms amide (–CONH–) linkages in the polymer chain.
75
What type of **linkage** is present in **polyamides such as nylon**?
Amide linkage ## Footnote The functional group is –CONH–.
76
# True or False: **Terylene** is an example of a **polyester**.
True ## Footnote It is formed from benzene-1,4-dicarboxylic acid and ethane-1,2-diol.
77
# Fill in the blank: **Nylon 6,6** is an example of a _\_\_\_\_\_\_ polymer.
polyamide ## Footnote Its repeating units are connected by amide bonds.
78
What type of **molecules** can polymerise by condensation to form **polyamides directly**?
Amino acids ## Footnote Each molecule contains both amine and carboxylic acid groups.
79
# True or False: **Condensation polymers** usually form by eliminating molecules such as **water**.
True ## Footnote The loss of a small molecule occurs during bond formation.
80
# Fill in the blank: Strong **intermolecular forces** between polyamide chains include _\_\_\_\_\_\_ bonding.
hydrogen ## Footnote The –CONH– groups allow hydrogen bonds to form.
81
What type of **intermolecular forces** mainly hold **polyester chains** together?
Dipole–dipole interactions ## Footnote These arise from the polar ester groups in the chain.
82
Why do **condensation polymers** such as **Kevlar** have high strength?
Strong intermolecular forces ## Footnote Hydrogen bonding and rigid structures increase mechanical strength.
83
What type of **polymers** are formed from **alkene monomers** and are generally non-biodegradable?
Polyalkenes ## Footnote Examples include poly(ethene) and poly(propene).
84
Why are **polyalkenes** resistant to **biodegradation**?
Chemically inert backbone ## Footnote Their chains contain only strong C–C and C–H bonds.
85
# Fill in the blank: **Polyalkenes** are difficult to break down because their polymer chains lack _\_\_\_\_\_\_ groups.
functional ## Footnote Functional groups are needed for hydrolysis reactions.
86
# True or False: **Polyesters** can be broken down by **hydrolysis**.
True ## Footnote Water can break the ester linkage in the polymer chain.
87
What type of **polymers** contain **ester linkages** that allow hydrolysis to occur?
Polyesters ## Footnote The –COO– linkage can react with water.
88
# True or False: **Polyamides** are biodegradable because their **amide bonds can be hydrolysed**.
True ## Footnote Water can break the –CONH– linkage under suitable conditions.
89
# Fill in the blank: The **linkage present in polyamides** that can be hydrolysed is the _\_\_\_\_\_\_ bond.
amide ## Footnote This bond can be broken by hydrolysis.
90
Why can **condensation polymers** be broken down by **hydrolysis**?
Reactive linkages ## Footnote Ester and amide bonds react with water.
91
# True or False: **Recycling polymers** reduces the need for **new raw materials**.
True ## Footnote It conserves fossil fuels and reduces waste.
92
# Fill in the blank: Breaking polymers down by heating in the **absence of oxygen** is called _\_\_\_\_\_\_.
pyrolysis ## Footnote This process can produce smaller hydrocarbons.
93
What is one **disadvantage of burning polymers** as a disposal method?
Toxic gases ## Footnote Combustion can release harmful gases such as CO or HCl.
94
Why are **biodegradable polymers** environmentally beneficial?
They break down naturally into less harmful substances. ## Footnote Microorganisms can degrade them.
95
What type of **organic compound** contains both an **amine group** and a **carboxylic acid group**?
Amino acid ## Footnote Amino acids contain –NH₂ and –COOH functional groups.
96
Why do amino acids show both **acidic and basic behaviour**?
Two functional groups: * a basic amine group (–NH₂) * an acidic carboxyl group (–COOH) ## Footnote This dual functionality allows amino acids to act as both acids and bases, contributing to their role in biological systems.
97
# Fill in the blank: A molecule containing **both positive and negative charges** is called a _\_\_\_\_\_.
zwitterion ## Footnote Amino acids commonly exist in this form in solution.
98
# True or False: In a **zwitterion**, the amino group is protonated and the carboxyl group is deprotonated.
True ## Footnote The structure contains –NH₃⁺ and –COO⁻ groups.
99
What form does an amino acid mainly exist in at neutral pH?
Zwitterion ## Footnote The molecule has both positive and negative charges but overall neutrality.
100
# True or False: In acidic solution, the **carboxyl group** of an amino acid exists as –COO⁻.
False ## Footnote In acidic conditions it becomes –COOH.
101
# Fill in the blank: In acidic solution, the amino group of an amino acid exists as _\_\_\_\_\_.
–NH₃⁺ ## Footnote The nitrogen atom becomes protonated.
102
What happens to the **carboxyl group** of an amino acid in **alkaline solution**?
Deprotonated ## Footnote It exists as the carboxylate ion –COO⁻.
103
# True or False: In alkaline solution, the **amino group** of an amino acid exists mainly as –NH₂.
True ## Footnote The proton is removed under basic conditions.
104
# Fill in the blank: In alkaline conditions, **amino acids** form ions containing _\_\_\_\_\_ and –NH₂ groups.
–COO⁻ ## Footnote The molecule becomes negatively charged overall.
105
Why are amino acids described as **amphoteric**?
React with acids and bases ## Footnote They can donate or accept protons.
106
What property allows amino acids to form **zwitterions**?
Internal proton transfer ## Footnote The –COOH group donates H⁺ to the –NH₂ group.
107
What type of **biological macromolecules** are formed from **amino acids** joined together?
Proteins ## Footnote Proteins are long chains of amino acids linked by peptide bonds.
108
What type of **bond** links amino acids together in proteins?
Peptide bond ## Footnote A peptide bond forms between the –COOH of one amino acid and –NH₂ of another.
109
# Fill in the blank: The **linkage** formed between amino acids in proteins is called a _\_\_\_\_\_ bond.
peptide ## Footnote This bond forms through a condensation reaction.
110
# True or False: Formation of a **peptide bond** involves the removal of a molecule of water.
True ## Footnote It is a condensation reaction between the carboxyl and amine groups.
111
What level of **protein structure** refers to the sequence of amino acids in the chain?
Primary structure ## Footnote This is determined by the order of amino acids in the polypeptide.
112
# True or False: The **α-helix** and **β-pleated sheet** are examples of secondary protein structure.
True ## Footnote These structures arise from hydrogen bonding in the backbone.
113
# Fill in the blank: Hydrogen bonding stabilises the _\_\_\_\_\_ structure of proteins.
secondary ## Footnote These bonds form between the C=O and N–H groups in the chain.
114
What type of **bond** can form between sulfur atoms in certain amino acids?
Disulfide bond ## Footnote These S–S bonds help stabilise protein structure.
115
# True or False: **Disulfide** bonds help maintain the **tertiary structure** of proteins.
True ## Footnote They form cross-links within the folded protein molecule.
116
# Fill in the blank: The **three-dimensional folding** of a protein molecule is called its _\_\_\_\_\_ structure.
tertiary ## Footnote This structure results from interactions between side chains.
117
What **process** breaks peptide bonds to release individual amino acids?
Hydrolysis ## Footnote Water reacts with the peptide bond to split it.
118
What chromatographic **technique** is used to separate amino acids in the laboratory?
Thin-layer chromatography ## Footnote Amino acids are identified using their Rf values.
119
What type of **biological molecules** act as catalysts in living organisms?
Enzymes ## Footnote Enzymes speed up biochemical reactions without being used up.
120
What type of **macromolecules** are enzymes made from?
Proteins ## Footnote Their structure is formed from folded polypeptide chains.
121
# Fill in the blank: The **region** of an enzyme where the **substrate binds** is called the _\_\_\_\_\_ site.
active ## Footnote This site has a specific shape complementary to the substrate.
122
# True or False: Enzymes act as **biological catalysts**.
True ## Footnote They increase reaction rate by lowering activation energy.
123
What molecule binds to the **active site** of an enzyme during a reaction?
Substrate ## Footnote The substrate fits into the enzyme’s active site.
124
# True or False: Enzyme active sites are **stereospecific**.
True ## Footnote They can only bind molecules with the correct three-dimensional shape.
125
# Fill in the blank: Enzymes are able to recognise specific molecules due to the _\_\_\_\_\_ of the **active site**.
shape ## Footnote The active site is complementary to the substrate.
126
Why can an enzyme bind only one **enantiomer** of a molecule?
Enzyme's active site is **stereospecific**. ## Footnote Only one mirror-image form fits the active site correctly.
127
# True or False: Enzyme inhibitors work by blocking the **active site** of an enzyme.
True ## Footnote This prevents the substrate from binding.
128
# Fill in the blank: A drug that prevents **substrate binding** by occupying the active site acts as an enzyme _\_\_\_\_\_.
inhibitor ## Footnote It reduces or stops enzyme activity.
129
What concept describes the matching **shapes** of enzyme active sites and substrates?
Lock-and-key model ## Footnote The substrate fits precisely into the active site.
130
How can computers assist in **modern drug development** targeting enzymes?
Molecular modelling ## Footnote Computer simulations help design molecules that fit enzyme active sites.
131
What large **biological molecule** carries **genetic information** in living organisms?
DNA ## Footnote DNA stands for deoxyribonucleic acid.
132
What are the **repeating units** that make up **DNA** called?
Nucleotides ## Footnote DNA is a polymer formed from many nucleotide monomers.
133
# Fill in the blank: Each **nucleotide** contains a phosphate group, a pentose sugar and a _\_\_\_\_\_.
base ## Footnote The base can be adenine, thymine, cytosine or guanine.
134
# True or False: The sugar present in DNA nucleotides is **2-deoxyribose**.
True ## Footnote It is a five-carbon sugar lacking one oxygen atom compared with ribose.
135
What are the **four nitrogen-containing bases** found in DNA?
* Adenine * Cytosine * Guanine * Thymine ## Footnote These bases attach to the sugar component of the nucleotide.
136
# True or False: DNA consists of a **single long chain** of nucleotides only.
False ## Footnote DNA forms two complementary strands.
137
# Fill in the blank: The **backbone of a DNA** strand consists of alternating _\_\_\_\_\_ and sugar units.
phosphate ## Footnote These form the sugar–phosphate backbone of the molecule.
138
What **shape** is formed when two DNA strands wind around each other?
Double helix ## Footnote The two strands twist together in a helical structure.
139
# True or False: **Hydrogen bonds** hold the **two strands of DNA** together.
True ## Footnote These bonds form between complementary bases.
140
# Fill in the blank: Adenine pairs with _\_\_\_\_\_ in DNA.
thymine ## Footnote These bases are connected by hydrogen bonds.
141
Which base pairs with **guanine** in DNA?
Cytosine ## Footnote G–C pairs are also held together by hydrogen bonds.
142
Why are the two strands of DNA described as **complementary**?
Specific base pairing ## Footnote Each base forms hydrogen bonds with only one specific partner.
143
What **platinum(II) complex** is commonly used as an anticancer drug?
Cisplatin ## Footnote Cisplatin contains Pt(II) coordinated to two chloride and two ammonia ligands in a cis configuration.
144
How does cisplatin interfere with cancer cell **DNA**?
Ligand replacement with guanine ## Footnote Cisplatin forms covalent bonds between platinum and nitrogen atoms on guanine bases.
145
# Fill in the blanks: By binding to DNA, cisplatin prevents _\_\_\_\_\_ _\_\_\_\_\_ of cancer cells.
DNA replication ## Footnote Cross-links distort the DNA structure, stopping replication.
146
# True or False: Cisplatin forms bonds with **adenine** in DNA to inhibit replication.
False ## Footnote Cisplatin primarily binds to guanine nitrogen atoms.
147
What type of **chemical reaction** occurs between cisplatin and DNA?
Ligand substitution ## Footnote Chloride ligands are replaced by nitrogen atoms in DNA.
148
# True or False: The **cis configuration** of cisplatin is important for its activity.
True ## Footnote The cis arrangement allows cross-linking of adjacent guanine bases.
149
# Fill in the blank: Drugs like **cisplatin** can have adverse effects because they also affect _\_\_\_\_\_ cells.
healthy ## Footnote Rapidly dividing normal cells can be damaged, causing side effects.
150
Why must the benefits and risks of **cisplatin** be carefully assessed?
Balance of therapeutic effect vs toxicity. ## Footnote It can kill cancer cells but also harm normal cells.
151
# True or False: Cisplatin is selective only for **cancer cells** and does not affect normal cells.
False ## Footnote Some normal rapidly dividing cells are also affected.
152
# Fill in the blank: **Cisplatin** prevents DNA replication by forming covalent cross-links between _\_\_\_\_\_ bases on DNA.
guanine ## Footnote Cross-linking distorts the double helix and blocks replication.
153
What is the **primary target of cisplatin** inside a cell?
DNA ## Footnote Binding to guanine bases disrupts replication and transcription.
154
Why does **cisplatin** cause side effects such as nausea and kidney damage?
Non-specific toxicity ## Footnote Healthy cells that divide rapidly or process the drug can be affected.
155
How can you visualise **amino acids** on a **TLC plate**?
Spray with ninhydrin or view under UV light.