Organic Chemistry: Amino Acids and Proteins
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Questions and Answers

What is a result of the decomposition of the benzenediazonium compound above 10°C?

  • Production of phenol (correct)
  • Creation of naphthalen-2-ol
  • Formation of azo dyes
  • Release of nitrogen gas

What is the purpose of the -OH or -NH2 group in benzenediazonium compounds?

  • It increases the electron density (correct)
  • It initiates decomposition
  • It decreases the electron density
  • It acts as a solvent

What is azo coupling characterized by?

  • Linking of two benzene rings (correct)
  • Absorption of UV light
  • Gain of a small molecule
  • Formation of an unstable complex

Which of the following best defines a chromophore?

<p>The structural unit responsible for color absorption (A)</p> Signup and view all the answers

If a compound absorbs light at a wavelength between 450nm and 490nm, what color will it appear?

<p>Orange (D)</p> Signup and view all the answers

What occurs when an α-amino acid is dissolved in a basic solution?

<p>It gains a proton. (A)</p> Signup and view all the answers

Which process leads to the formation of a dipeptide?

<p>Condensation reaction. (D)</p> Signup and view all the answers

What defines the primary structure of a protein?

<p>The sequence of amino acids in the polypeptide chain. (A)</p> Signup and view all the answers

Which of the following amino acids is considered essential in the human diet?

<p>Valine (A)</p> Signup and view all the answers

What type of bond is formed during the condensation reaction between two amino acids?

<p>Peptide bond. (A)</p> Signup and view all the answers

How many amino acids can the human body synthesize on its own?

<p>12 (B)</p> Signup and view all the answers

What property do zwitterions of amino acids exhibit due to their ionic nature?

<p>High melting points. (B)</p> Signup and view all the answers

When proteins undergo condensation reactions, what type of macromolecule is primarily formed?

<p>Polypeptides. (C)</p> Signup and view all the answers

What is required for a Friedel-Crafts reaction?

<p>A halogen carrier such as AlCl3 or FeCl3 (C)</p> Signup and view all the answers

What product is formed when compound C reacts with Tollen's reagent?

<p>A silver mirror (B)</p> Signup and view all the answers

Which statement accurately describes optical isomerism?

<p>It involves molecules with chiral carbon atoms (C)</p> Signup and view all the answers

In the conversion of compound C to a carboxylic acid, which oxidizing agent is used?

<p>Acidified potassium dichromate(VI) (B)</p> Signup and view all the answers

What result may occur due to unreacted products in a reversible chemical reaction?

<p>Introduction of additional contaminating substances (A)</p> Signup and view all the answers

What is a characteristic of miscible liquids in terms of their reactions?

<p>They do not form distinct layers (C)</p> Signup and view all the answers

Which of the following does NOT represent a common property of organic reactions?

<p>Guaranteed high purity of products (A)</p> Signup and view all the answers

Which condition is ideal for performing a Friedel-Crafts reaction?

<p>At room temperature and in the dark (C)</p> Signup and view all the answers

What type of reaction occurs when an alkyl group is added to a benzene ring?

<p>Electrophilic substitution (D)</p> Signup and view all the answers

Which catalyst is commonly used in the alkylation of benzene?

<p>Aluminium chloride (A)</p> Signup and view all the answers

What reaction mechanism do chloroalkanes undergo when reacting with NaOH?

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

Why is the C-Cl bond in chlorobenzene stronger than in chloroalkanes?

<p>The overlap of lone pairs with π-electrons (A)</p> Signup and view all the answers

What is needed to convert chlorobenzene to phenol?

<p>High temperatures and pressures (D)</p> Signup and view all the answers

Which types of alcohols are formed from the reduction of aldehydes?

<p>Primary alcohols only (C)</p> Signup and view all the answers

Which of the following statements about primary and secondary alcohols is true?

<p>Primary alcohols have -OH connected to a carbon attached to one or no other carbon (C)</p> Signup and view all the answers

What is the main characteristic that distinguishes stereoisomers from structural isomers?

<p>Stereoisomers have the same arrangement of atoms but different spatial arrangements. (C)</p> Signup and view all the answers

What is NOT a method for the formation of alcohols?

<p>Substitution reaction from alcohols (C)</p> Signup and view all the answers

Which type of isomerism is characterized by the inability of atoms or groups to rotate around a double bond?

<p>E/Z isomerism (A)</p> Signup and view all the answers

In E/Z isomerism, what does the 'E' designation indicate?

<p>Atoms or groups are opposite each other. (B)</p> Signup and view all the answers

What effect do optical isomers have on plane polarized light?

<p>They rotate the plane of polarized light in different directions. (A)</p> Signup and view all the answers

Which of the following is an example of E/Z isomerism?

<p>2-chloro,4-methylpent-2-ene (B)</p> Signup and view all the answers

Which statement regarding optical isomers is incorrect?

<p>They have identical physical properties. (A)</p> Signup and view all the answers

What is required for a compound to exhibit E/Z isomerism?

<p>Presence of a double bond (C)</p> Signup and view all the answers

Which of the following examples represents an E isomer?

<p>(E)-2-chloro,4-methylpent-2-ene (D)</p> Signup and view all the answers

Which isomer has a straight chain structure consisting of five carbon atoms?

<p>Isomer P (B)</p> Signup and view all the answers

Which isomer features a chiral center with four different groups on a carbon atom?

<p>Isomer Q (C)</p> Signup and view all the answers

Which characteristic describes the NMR spectrum of Isomer R?

<p>Two peaks, both singlets (A)</p> Signup and view all the answers

What is likely the environment of the protons in Isomer T that corresponds to the yellow highlights?

<p>CH3-CO (C)</p> Signup and view all the answers

In the NMR spectrum of Isomer T, what is the splitting pattern expected for the green proton environment?

<p>Singlet (A)</p> Signup and view all the answers

Which structure represents Isomer S?

<p>Methyl group on third carbon (C)</p> Signup and view all the answers

What would the chemical shift (ppm) for the CH3-CO environment in Isomer T be approximately?

<p>2.0 to 2.5 ppm (B)</p> Signup and view all the answers

Which of the following accurately describes the molecular formula of Isomer P?

<p>C5H10O2 (C)</p> Signup and view all the answers

Flashcards

Stereoisomerism

A type of isomer where compounds have the same arrangement of atoms, but different spatial arrangements of their bonds. There are two forms: E/Z isomerism and optical isomerism.

E/Z Isomerism

A type of stereoisomerism where different atoms or groups are bonded to the carbon atoms of a double bond. The E-isomer has atoms or groups opposite each other, while the Z-isomer has them on the same side of the double bond.

Chirality

A molecule that contains a center of chirality, commonly a carbon atom bonded to four different atoms or groups. The molecule's mirror image cannot be superimposed on the original.

Enantiomers

Optical isomers that rotate the plane of polarized light in opposite directions. One isomer rotates the plane to the left (levo-rotatory) and the other to the right (dextrorotatory).

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Optical Activity

The ability of a molecule to rotate the plane of polarized light. This property is exhibited by molecules with a chiral center.

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Geometric Isomerism

A type of stereoisomerism where molecules have the same molecular formula and the same sequence of atoms but differ in the spatial arrangement of their atoms due to restricted rotation around a double bond. E/Z isomerism is a subcategory of this type.

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Chiral Center

A compound that contains a carbon atom bonded to four different atoms or groups. These compounds exhibit optical isomerism.

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Optical Rotation

The ability of a substance to rotate the plane of polarized light. This is observed in molecules that contain a chiral center.

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Chromophore

A group of atoms that are responsible for absorbing light at a specific wavelength, and that is essential for color in molecules.

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Azo Coupling

A chemical reaction that occurs when a benzenediazonium ion reacts with an aromatic compound containing an electron-rich group like -OH or -NH2. The resulting molecule has a -N=N- (azo) group linking two benzene rings.

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Color and Wavelength Absorption

The color of a compound is determined by the wavelength of light it absorbs. The color we see is the complementary color to the one absorbed. For example, if a compound absorbs blue light, it will appear orange.

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Benzenediazonium Compound Decomposition

Phenol is produced when benzenediazonium compounds decompose above 10 degrees Celsius. This reaction resembles the decomposition of aliphatic amines.

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Reactions of Benzenediazonium Salts

Benzenediazonium salts are highly reactive and react with phenols and aromatic amines below 10 degrees Celsius. This reaction forms azo dyes, which have the -N=N- (azo) group linking two benzene rings.

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Alkylation of Benzene (Friedel-Crafts)

A type of reaction where an alkyl group (like methyl or ethyl) is added to a benzene ring by replacing a hydrogen atom. It uses a halogenoalkane and a catalyst like aluminium chloride.

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Nucleophilic Substitution

A reaction where a nucleophile (like OH-) replaces a halogen atom in a molecule. This is common for chloroalkanes.

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Reduction of Aldehydes, Ketones, or Carboxylic Acids

A reaction where electrons are added to a molecule, like an aldehyde or ketone, to form an alcohol. It's a chemical reduction process.

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Primary Alcohol

Alcohols with their -OH group attached to a carbon that's connected to only one other carbon atom.

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Secondary Alcohol

Alcohols with their -OH group attached to a carbon that's connected to two other carbon atoms.

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Tertiary Alcohol

Alcohols with their -OH group attached to a carbon that's connected to three other carbon atoms.

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C-Cl bond in Chlorobenzene vs. Chloroalkanes

The strength of the bond between the carbon and chlorine atom in chlorobenzene is greater than in chloroalkanes. This makes chlorobenzene more stable and less reactive with nucleophiles.

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Overlap of Electrons in Chlorobenzene

The reason for the stronger C-Cl bond in chlorobenzene is that the lone pairs on the chlorine atom overlap with the pi electrons in the benzene ring. This makes the bond stronger and less likely to break.

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Zwitterion

A molecule with both positive and negative charges, typically in a stable, neutral form. It arises when a proton moves from the carboxyl group (-COOH) to the amino group (-NH2) in an amino acid.

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Amphoteric

The ability of a substance to act as both an acid and a base. Amino acids can donate a proton (acting as an acid) or accept a proton (acting as a base), depending on the pH of the surrounding environment.

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Dipeptide Formation

A process where two amino acids combine to form a larger molecule, a dipeptide. This involves the removal of a water molecule (condensation reaction).

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Peptide Bond

The repeating link between amino acids in polypeptides and proteins. It's formed by a condensation reaction between the carboxyl group of one amino acid and the amino group of another.

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Polypeptide

A chain of amino acids linked by peptide bonds. These chains can be short (oligopeptides) or long (polypeptides).

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Primary Structure

The order of amino acids in a polypeptide chain. This sequence determines the protein's unique shape and function.

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Essential Amino Acids

Amino acids that the human body can make or obtain from the diet, contributing to the various proteins we need.

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Protein Structure

The three-dimensional structure of a protein, influencing its biological function. It's determined by the interactions between the amino acid side chains.

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Friedel-Crafts Reaction

A chemical reaction where a carbon chain is added to a benzene ring. Requires a specific carbon chain and a halogen carrier (like AlCl3 or FeCl3) for the reaction to occur.

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Separation and Purification

The process of separating and purifying desired products from a mixture by taking advantage of their different properties, like boiling points or solubility.

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Optical Isomerism

A type of isomerism where molecules have the same arrangement of atoms but different spatial arrangements. Their mirror images cannot be superimposed.

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Chiral Carbon

A carbon atom bonded to four different groups. This creates a chiral center, leading to optical isomerism.

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Hydrolysis of a Nitrile

A chemical reaction where a nitrile is heated with dilute acid to produce a carboxylic acid.

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Oxidation of an Aldehyde

A chemical reaction where an aldehyde is oxidized to a carboxylic acid using an oxidizing agent like acidified potassium dichromate(VI).

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Pentanoic Acid (Isomer P)

A compound with the same molecular formula as another compound but a different arrangement of atoms. It has all five carbon atoms in a straight chain.

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Isomer Q

A molecule with a chiral center, meaning it has four different atoms or groups bonded to a carbon atom. The molecule and its mirror image cannot be superimposed.

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Isomer R

A molecule that has only two different hydrogen environments, as indicated by its NMR spectrum. The two peaks in the spectrum are singlets, meaning each hydrogen environment is not next to another hydrogen.

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Isomer S

An isomer with the same structural formula as isomer Q but with the methyl group on the third carbon atom instead of the second.

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What is NMR spectroscopy?

A spectral technique analyzing the magnetic properties of atomic nuclei, particularly hydrogen nuclei. Its peaks indicate the presence of different hydrogen environments within a molecule, providing information about the structure and bonding of the molecule.

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How many signals does NMR give?

The number of signals in an NMR spectrum corresponds to the number of different hydrogen environments in a molecule.

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What is the splitting pattern in NMR?

The splitting pattern of signals in NMR spectroscopy is determined by the number of neighboring hydrogen atoms. For example, a singlet indicates no neighboring hydrogens, a doublet indicates one neighboring hydrogen, a triplet indicates two neighboring hydrogens, and so on.

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What is chemical shift in NMR?

The chemical shift in NMR spectroscopy refers to the specific position of a signal in the spectrum. Different functional groups and environments influence the chemical shift values. For example, hydrogens attached to a carbonyl group (C=O) typically have a higher chemical shift value than hydrogens attached to an alkyl group (C-H).

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Study Notes

Organic Chemistry - Unit 4

  • This revision guide is for GCE A Level WJEC Chemistry Unit 4, focusing on organic chemistry and analysis.
  • The notes were authored by experienced teachers to support student revision for their GCE A Level exams.
  • The notes aim to be comprehensive but may not cover all aspects of the specification.
  • The notes do not represent the full depth of knowledge required for the unit.

Content Outline

  • 4.1 - Stereoisomerism: Covers E/Z isomerism and optical isomerism.
  • 4.2 - Aromaticity: Discusses the structure and reactions of benzene.
  • 4.3 - Alcohols and phenols: Delves into the formation and reactions of alcohols and phenols.
  • 4.4 - Aldehydes and ketones: Details the structure, nomenclature, and reactions of aldehydes and ketones.
  • 4.5 - Carboxylic acids: Covers the structure, nomenclature, and reactions of carboxylic acids, including comparing their acidity to other compounds.
  • **4.6 - Amines:**Explores the formation, reactions, properties, and nomenclature of amines.
  • 4.7 - Amino acids, peptides, and proteins: Covers the formation of dipeptides and polypeptides, and the amphoteric nature of amino acids.
  • 4.8 - Organic synthesis and analysis: Details the synthesis of organic compounds and different experimental techniques.

4.1 - Stereoisomerism (E/Z)

  • E/Z isomers have the same atoms/groups but differ in their spatial arrangement.
  • E/Z isomerism is centred on C=C double bonds.
  • The E isomer has opposite groups on either side of the double bond.
  • The Z isomer has identical groups on the same side of the double bond.
  • The ability of atoms or groups to rotate around the double bond is limited.

4.1 - Stereoisomerism (Optical)

  • Optical isomers are mirror images of each other that cannot be superimposed.
  • A chiral center has four different groups bonded to it.
  • Optical isomers rotate the plane of plane-polarized light in opposite directions.
  • A racemic mixture contains equal amounts of both optical isomers, resulting in no net rotation of plane-polarized light.

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Test your knowledge on organic chemistry concepts related to amino acids, proteins, and their reactions. This quiz covers topics such as dipeptide formation, essential amino acids, and the structural properties of proteins. Perfect for students studying organic chemistry.

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