Organic Chemistry Unit 4 Revision Guide

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Questions and Answers

Which compound is known as methanoic acid?

  • Formic acid (correct)
  • Butanone
  • Propanone
  • Ethanol

Which distillation method is specifically used for separating components with significantly different boiling points?

  • Simple distillation
  • Fractional distillation (correct)
  • Vacuum filtration
  • Steam distillation

What is the primary structural classification of proteins that involves the overall three-dimensional shape?

  • Secondary structure
  • Tertiary structure (correct)
  • Quaternary structure
  • Primary structure

In spectroscopy, which type of NMR is commonly used to analyze the hydrogen environment in organic compounds?

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

Which acid is also referred to as acetic acid?

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

What type of amine is formed when nitrogen is bonded to three carbon atoms?

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

Which reaction condition is necessary to avoid the escape of ammonia during the formation of aliphatic amines?

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

What product is formed when propylamine reacts with excess halogenoalkane?

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

What is the effect of heating an ammonium salt with aqueous NaOH?

<p>Production of an amine (C)</p> Signup and view all the answers

In the reduction of nitrobenzene to form phenylamine, which is the reducing agent commonly used?

<p>Tin with conc HCl (D)</p> Signup and view all the answers

What defines the basic nature of amines compared to ammonia?

<p>Lone pair of electrons on nitrogen (A)</p> Signup and view all the answers

What is one method for producing aliphatic amines from nitriles?

<p>Reduction using LiAlH4 (C)</p> Signup and view all the answers

What happens when an amine reacts with HBr?

<p>Creation of an ammonium halide salt (A)</p> Signup and view all the answers

What does the ratio of peak heights in the NMR spectrum indicate?

<p>The number of hydrogen atoms in the environment. (B)</p> Signup and view all the answers

How many peaks would be seen for a hydrogen atom adjacent to three other hydrogen atoms?

<p>Four peaks. (B)</p> Signup and view all the answers

What is the splitting rule for hydrogen atoms in an NMR spectrum?

<p>The peak is split based on the number of hydrogen atoms adjacent to them plus one. (A)</p> Signup and view all the answers

In the spectrum described, how many peaks do the green protons have?

<p>One peak. (B)</p> Signup and view all the answers

What does an increasing number of peaks in an NMR spectrum typically indicate?

<p>More hydrogen atoms adjacent to the observed protons. (D)</p> Signup and view all the answers

What characteristic of the red protons is noted in the spectrum?

<p>They have four peaks. (C)</p> Signup and view all the answers

Which statement about the relationship between peak height and hydrogen atoms is accurate?

<p>Peak height correlates directly with the number of hydrogen atoms in the environment. (A)</p> Signup and view all the answers

How many peaks do the blue protons have in the NMR spectrum?

<p>Three peaks. (B)</p> Signup and view all the answers

What step is necessary if crystals do not form during cooling?

<p>Boil the solution again (C)</p> Signup and view all the answers

What is the purpose of dissolving crystals in a hot solvent during purification?

<p>To remove impurities (C)</p> Signup and view all the answers

What characterizes a compound that is impure based on melting point observation?

<p>Melting temperature is lower than anticipated (D)</p> Signup and view all the answers

What type of bonds are primarily formed in addition polymerisation?

<p>Single bonds between carbon atoms (B)</p> Signup and view all the answers

Which of the following characteristics distinguishes condensation polymerisation from addition polymerisation?

<p>Small molecules are released during condensation polymerisation (B)</p> Signup and view all the answers

What types of functional groups are typically involved in condensation polymerisation?

<p>-OH, -COOH, -NH2 (C)</p> Signup and view all the answers

What is a common use of polyesters formed by condensation polymerisation?

<p>Creating plastic bottles and clothing (A)</p> Signup and view all the answers

Which of the following statements is accurate regarding the products of addition polymerisation?

<p>Only the polymer is formed in addition polymerisation without by-products (D)</p> Signup and view all the answers

What is the most common method for producing esters?

<p>Refluxing reactants with concentrated H2SO4 (C)</p> Signup and view all the answers

Why are phenols considered stronger acids than alcohols?

<p>They can form stable phenoxide ions (D)</p> Signup and view all the answers

How does the presence of electron-attracting groups on the benzene ring affect the acidity of phenol?

<p>It increases the acidity by weakening the O-H bond (B)</p> Signup and view all the answers

What indicates that phenols are less acidic than carboxylic acids?

<p>Phenols do not produce CO2 gas with sodium carbonate (B)</p> Signup and view all the answers

What property of phenol makes it more susceptible to electrophilic attack compared to benzene?

<p>Lone pair overlap with π-electrons (C)</p> Signup and view all the answers

How is the stability of the phenoxide ion increased?

<p>Through the delocalization of the negative charge (D)</p> Signup and view all the answers

Which of the following correctly describes phenol's solubility properties?

<p>Phenol dissolves in sodium hydroxide due to its acidic nature (D)</p> Signup and view all the answers

What effect does the boiling temperature of ester have after production?

<p>It influences the method of separation from the mixture (A)</p> Signup and view all the answers

What is the chemical shift range for the blue compound (CH3CH2-O)?

<p>2.5 to 3.0 ppm (B)</p> Signup and view all the answers

How many peaks will the pink compound (CH3CH2) have in a NMR spectrum?

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

What is the stationary phase in thin layer chromatography?

<p>Silica or aluminum oxide (D)</p> Signup and view all the answers

Which of the following statements about Rf values in chromatography is correct?

<p>Rf must always be less than 1 (D)</p> Signup and view all the answers

What happens if you obtain an Rf value of 1 in thin layer chromatography?

<p>You need to try a different solvent (B)</p> Signup and view all the answers

What is the mobile phase in paper chromatography?

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

Which of these compounds would likely appear in the chemical shift range of 0.1 to 2.0 ppm?

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

In relation to peaks in NMR spectroscopy, what is the significance of having multiple peaks?

<p>It reflects the environment of hydrogens in the molecule (D)</p> Signup and view all the answers

Flashcards

Primary Amines

Amines where the nitrogen atom is bonded to one carbon atom.

Secondary Amines

Amines where the nitrogen atom is bonded to two carbon atoms.

Tertiary Amines

Amines where the nitrogen atom is bonded to three carbon atoms.

Aromatic Amines

Aromatic amines have their nitrogen atom directly bonded to the benzene ring.

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Formation of Aliphatic Amines - From Halogenoalkanes

In a sealed tube, a halogenoalkane reacts with excess ammonia to form an amine.

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Formation of Aliphatic Amines - From Nitriles

Nitriles can be reduced to amines using LiAlH4.

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Formation of Aromatic Amines

Nitrobenzene is reduced to phenylamine using tin and concentrated hydrochloric acid.

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Basic Nature of Amines

Amines are basic because the nitrogen atom has a lone pair of electrons that can accept a proton.

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Esterification

A reaction where an ester is formed by reacting a carboxylic acid and an alcohol in the presence of a strong acid catalyst (e.g., concentrated H2SO4).

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Ester

An organic compound with the general formula R-COOR', where R and R' are alkyl or aryl groups, formed by the reaction of a carboxylic acid and an alcohol.

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Phenol

A type of organic compound that contains a hydroxyl (-OH) group directly attached to a benzene ring.

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Acidity of Phenol

The ability of phenol to donate a proton (H+) to form a phenoxide ion, making it acidic.

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Reaction of Phenol with Bromine

The process of reacting a phenol with bromine to form halophenols, where one or more bromine atoms are substituted onto the benzene ring.

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Reaction of Phenol with Ethanoyl Chloride

The process of reacting a phenol with ethanoyl chloride to form an ester where the -OH group is replaced with an -OCOCH3 group.

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Reaction of Phenol with Iron(III) Chloride

The reaction of phenol with iron(III) chloride solution, which produces a violet-colored solution, indicating the presence of phenol.

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Effect of Substituents on Phenol Acidity

Substituents on the benzene ring in phenol can affect its acidity. Electron-withdrawing groups (e.g., Cl-) increase acidity by making the O-H bond weaker.

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Rf value

The distance a compound travels relative to the solvent front in chromatography.

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Silica or aluminum oxide

A stationary phase used in thin-layer chromatography (TLC). It's often a thin layer of silica gel or aluminum oxide on a glass plate.

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Chromatography

A technique used to separate substances based on their movement through a stationary phase. The substances are carried by a solvent.

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Mobile phase

The solvent in chromatography is the mobile phase and it moves up the stationary phase, separating the substances.

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Stationary phase

The substance or material that doesn’t move in chromatography. It's usually paper, silica gel, or aluminum oxide.

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Solvent front

It is the distance travelled by the solvent.

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Stop the process

When the solvent front reaches a certain height, the process is stopped. The paper or plate is dried and analyzed.

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Thin layer chromatography (TLC)

The technique uses a layer of silica or aluminum oxide coated on a glass plate as the stationary phase. Samples are spotted on the plate and placed in a jar with a solvent. The solvent moves up the plate, separating the mixture into different spots.

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NMR Peak Height

The relative height of an NMR peak is directly proportional to the number of hydrogen atoms in that chemical environment.

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NMR Signal Splitting

The number of peaks a signal is split into is determined by the number of neighboring hydrogen atoms. The signal will be split into (n+1) peaks, where 'n' is the number of neighboring hydrogens.

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NMR Signal: No Neighboring Hydrogens

If a hydrogen atom has no neighboring hydrogen atoms, its signal will appear as a single peak in the NMR spectrum. This is because there is no splitting caused by neighboring hydrogens.

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NMR Signal: Two Neighboring Hydrogens

When a hydrogen atom has two neighboring hydrogen atoms, its NMR signal will be split into three peaks due to the interaction between the neighboring hydrogens.

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NMR Signal: Three Neighboring Hydrogens

When a hydrogen atom has three neighboring hydrogen atoms, its NMR signal will be split into four peaks due to the interaction between the neighboring hydrogens.

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NMR Peak Height Ratio

In a molecule with several different types of hydrogens, the relative heights of the peaks in the NMR spectrum reflect the number of hydrogens in each environment.

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Isomers

Isomers are molecules with the same molecular formula but different structural formulas, leading to different arrangements of atoms and functional groups within the molecule.

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Functional Groups

In organic chemistry, functional groups are specific groups of atoms within a molecule that have characteristic chemical properties and behaviors.

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Aldehyde

An organic compound containing a carbonyl group (C=O) bonded to a hydrogen atom and an alkyl or aryl group. Example: Ethanal (CH3CHO).

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Ketone

An organic compound containing a carbonyl group (C=O) bonded to two alkyl or aryl groups. Example: Propanone (CH3COCH3).

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Carboxylic acid

An organic compound containing a carboxyl group (-COOH) attached to an alkyl or aryl group. Example: Ethanoic acid (CH3COOH).

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Proton NMR (Nuclear Magnetic Resonance)

A type of spectroscopy that uses the absorption of radio waves by atomic nuclei to determine the structure of molecules.

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Recrystallization

A method for purifying a solid, involving dissolving the crystals in the minimum amount of hot solvent, filtering to remove impurities, cooling the solution, filtering again, washing the crystals with a small amount of solvent, and finally drying them between filter paper.

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Melting Point Determination

A technique used to test the purity of a solid by observing the temperature at which it transitions from a solid to a liquid. Pure compounds have a narrow melting point range, while impure ones melt over a wider range and at a lower temperature.

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Condensation Polymerization

The process of forming a polymer by joining monomers together with the loss of a small molecule, typically water or HCl.

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Addition Polymerization

The process of forming a polymer by joining monomers together without the loss of any atoms, typically by opening a double bond (usually in alkene monomers).

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Polyester

A type of condensation polymer formed from the reaction of a dicarboxylic acid and a dialcohol (diol), with the loss of water molecules. Common examples include PET (polyethylene terephthalate) used for plastic bottles and polyester clothing.

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Polyamide

A type of condensation polymer formed from the reaction of a diamine and a diacid, with the loss of water molecules. These polymers are typically strong and durable, used in materials such as nylon and Kevlar.

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Alkene

A monomer commonly used in addition polymerization that contains a double bond between carbon atoms. The double bond breaks during polymerization, forming single bonds and allowing monomers to join together.

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Small Molecule Loss

A small molecule, typically water (H2O) or hydrochloric acid (HCl), that is lost during condensation polymerization. These molecules are removed from the functional groups of the monomers as they link together.

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Study Notes

Organic Chemistry Unit 4 - Revision Guide

  • This revision guide covers GCE A Level WJEC Chemistry Unit 4, Organic Chemistry and Analysis.
  • It's intended as a supplementary resource and may not cover every aspect of the specification.
  • The guide includes content on topics like stereoisomerism, aromaticity, alcohols, phenols, aldehydes, ketones, carboxylic acids, amines, amino acids, peptides, proteins, organic synthesis, and analysis.
  • Specific sections cover topics like stereoisomerism (E/Z isomers), optical isomerism, aromaticity (benzene structure and reactions like nitration and halogenation), alcohols (primary, secondary, tertiary), making alcohols, reactions of alcohols, carboxylic acids (acidity and oxidation reactions), alkylbenzenes, phenol's acidity and reaction with bromine, amines (formation and types), and amide and nitrile formation, reaction, and hydrolysis.
  • The guide also mentions different tests for the identification of different organic compounds, including tests for carbonyl compounds, such as the Tollens' and Fehling's tests, and the iodoform test, hydrolysis reactions, and separation techniques like chromatography (paper, thin-layer, gas), distillation, and crystallization.
  • Formation and reactions of esters and polyesters are addressed, as well as methods for making carboxylic acids.
  • This guide includes practical details, including reaction conditions, reagents used, and observed changes during experiments on organic synthesis and analysis.

Content Outline (by Page Number)

  • Page 3: Stereoisomerism
  • Page 5: Aromaticity
  • Page 9: Alcohols and phenols
  • Page 13: Aldehydes and ketones
  • Page 17: Carboxylic acids
  • Page 21: Amines
  • Page 27: Amino acids, peptides, and proteins
  • Page 31: Organic synthesis and analysis
  • Page 43: Acknowledgments

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