Topic 10: Organic Chemistry: Halogenoalkanes, Alcohols and Spectra

Be able to classify reactions (including those in Unit 1) as addition, elimination, substitution, oxidation, reduction, hydrolysis or polymerisation.

Use —classify reactions (including those in unit 1) as addition, elimination, substitution, oxidation, reduction, hydrolysis or to connect the rule to the data and decision in the question.

This matters because —classify reactions (including those in unit 1) as addition, elimination, substitution, oxidation, reduction, hydrolysis or determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —classify reactions (including those in unit 1) as addition, elimination, substitution, oxidation, reduction, hydrolysis or to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Classify reactions (including those in Unit 1) as addition, elimination, substitution, oxidation, reduction, hydrolysis or is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the concept of a reaction mechanism.

Use —the concept of a reaction mechanism to connect the rule to the data and decision in the question.

This matters because —the concept of a reaction mechanism determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the concept of a reaction mechanism to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The concept of a reaction mechanism is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that heterolytic bond breaking results in species that are electrophiles or nucleophiles.

Use —heterolytic bond breaking results in species that are electrophiles or nucleophiles to connect the rule to the data and decision in the question.

This matters because —heterolytic bond breaking results in species that are electrophiles or nucleophiles determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —heterolytic bond breaking results in species that are electrophiles or nucleophiles to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Heterolytic bond breaking results in species that are electrophiles or nucleophiles is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Know the definition of the term ‘nucleophile’.

Use —the definition of the term ‘nucleophile’ to connect the rule to the data and decision in the question.

This matters because —the definition of the term ‘nucleophile’ determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the definition of the term ‘nucleophile’ to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The definition of the term ‘nucleophile’ is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the link between bond polarity and the type of reaction mechanism a compound will undergo 10B: Halogenoalkanes Students will be assessed on their ability to:.

Use —the link between bond polarity and the type of reaction mechanism a compound will undergo 10b: halogenoalkanes students will to connect the rule to the data and decision in the question.

This matters because —the link between bond polarity and the type of reaction mechanism a compound will undergo 10b: halogenoalkanes students will determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the link between bond polarity and the type of reaction mechanism a compound will undergo 10b: halogenoalkanes students will to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The link between bond polarity and the type of reaction mechanism a compound will undergo 10B: Halogenoalkanes Students will is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the nomenclature of halogenoalkanes and be able to draw their structural, displayed and skeletal formulae.

Use —the nomenclature of halogenoalkanes to connect the rule to the data and decision in the question.

This matters because —the nomenclature of halogenoalkanes determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the nomenclature of halogenoalkanes to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The nomenclature of halogenoalkanes is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the distinction between primary, secondary and tertiary halogenoalkanes.

Use —the distinction between primary, secondary and tertiary halogenoalkanes to connect the rule to the data and decision in the question.

This matters because —the distinction between primary, secondary and tertiary halogenoalkanes determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the distinction between primary, secondary and tertiary halogenoalkanes to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The distinction between primary, secondary and tertiary halogenoalkanes is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the reactions of halogenoalkanes with: i aqueous alkali, including KOH(aq) to produce alcohols (where the hydroxide ion acts as a nucleophile) ii ethanolic potassium hydroxide to produce alkenes by an elimination reaction (where the hydroxide ion acts as a base) iii aqueous silver nitrate in ethanol (where water acts as a nucleophile) iv alcoholic ammonia under pressure to produce amines (where the ammonia acts as a nucleophile) v alcoholic potassium cyanide to produce nitriles (where the cyanide ion acts as a nucleophile) Students should know this is an example of increasing the length of the carbon chain.

Use —the reactions of halogenoalkanes with: i aqueous alkali to connect the rule to the data and decision in the question.

This matters because —the reactions of halogenoalkanes with: i aqueous alkali determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the reactions of halogenoalkanes with: i aqueous alkali to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The reactions of halogenoalkanes with: i aqueous alkali is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and: i aqueous potassium hydroxide ii ammonia SN1 and SN2 substitution mechanisms will be tested in Unit 4.

Use —the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and: i aqueous potassium hydroxide to connect the rule to the data and decision in the question.

This matters because —the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and: i aqueous potassium hydroxide determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and: i aqueous potassium hydroxide to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The mechanisms of the nucleophilic substitution reactions between primary halogenoalkanes and: i aqueous potassium hydroxide is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that experimental observations and data can be used to compare the relative rates of hydrolysis of: i primary, secondary and tertiary structural isomers of a halogenoalkane ii primary chloro-, bromo- and iodoalkanes using aqueous silver nitrate in ethanol.

Use —experimental observations and data can be used to compare the relative rates of hydrolysis of: i primary, secondary to connect the rule to the data and decision in the question.

This matters because —experimental observations and data can be used to compare the relative rates of hydrolysis of: i primary, secondary determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —experimental observations and data can be used to compare the relative rates of hydrolysis of: i primary, secondary to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Experimental observations and data can be used to compare the relative rates of hydrolysis of: i primary, secondary is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

CORE PRACTICAL 5 Investigation of the rates of hydrolysis of some halogenoalkanes.

Use —core practical 5 investigation of the rates of hydrolysis of some halogenoalkanes to connect the rule to the data and decision in the question.

This matters because —core practical 5 investigation of the rates of hydrolysis of some halogenoalkanes determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —core practical 5 investigation of the rates of hydrolysis of some halogenoalkanes to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —CORE PRACTICAL 5 Investigation of the rates of hydrolysis of some halogenoalkanes is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Know the trend in reactivity of primary, secondary and tertiary halogenoalkanes.

Use —the trend in reactivity of primary, secondary and tertiary halogenoalkanes to connect the rule to the data and decision in the question.

This matters because —the trend in reactivity of primary, secondary and tertiary halogenoalkanes determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the trend in reactivity of primary, secondary and tertiary halogenoalkanes to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The trend in reactivity of primary, secondary and tertiary halogenoalkanes is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand, in terms of bond enthalpy, the trend in reactivity of chloro-, bromo- and iodoalkanes.

Use —understand, in terms of bond enthalpy, the trend in reactivity of chloro-, bromo- and iodoalkanes to connect the rule to the data and decision in the question.

This matters because —understand, in terms of bond enthalpy, the trend in reactivity of chloro-, bromo- and iodoalkanes determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —understand, in terms of bond enthalpy, the trend in reactivity of chloro-, bromo- and iodoalkanes to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Understand, in terms of bond enthalpy, the trend in reactivity of chloro-, bromo- and iodoalkanes is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

CORE PRACTICAL 6 Chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid.

Use —core practical 6 chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid to connect the rule to the data and decision in the question.

This matters because —core practical 6 chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —core practical 6 chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —CORE PRACTICAL 6 Chlorination of 2-methylpropan-2-ol with concentrated hydrochloric acid is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the nomenclature of alcohols and be able to draw their structural, displayed and skeletal formulae.

Use —the nomenclature of alcohols to connect the rule to the data and decision in the question.

This matters because —the nomenclature of alcohols determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the nomenclature of alcohols to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The nomenclature of alcohols is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the distinction between primary, secondary and tertiary alcohols.

Use —the distinction between primary, secondary and tertiary alcohols to connect the rule to the data and decision in the question.

This matters because —the distinction between primary, secondary and tertiary alcohols determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the distinction between primary, secondary and tertiary alcohols to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The distinction between primary, secondary and tertiary alcohols is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand the reactions of alcohols with: i oxygen in air (combustion) ii halogenating agents PCl5 to produce chloroalkanes (including its use as a qualitative test for the presence of the –OH group) 50% concentrated sulfuric acid and potassium bromide to produce bromoalkanes red phosphorus and iodine to produce iodoalkanes iii concentrated phosphoric acid to form alkenes by elimination Descriptions of the mechanisms of these reactions are not required.

Use —the reactions of alcohols with: i oxygen in air (combustion) ii halogenating agents • pcl5 to produce chloroalkanes to connect the rule to the data and decision in the question.

This matters because —the reactions of alcohols with: i oxygen in air (combustion) ii halogenating agents • pcl5 to produce chloroalkanes determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —the reactions of alcohols with: i oxygen in air (combustion) ii halogenating agents • pcl5 to produce chloroalkanes to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —The reactions of alcohols with: i oxygen in air (combustion) ii halogenating agents • PCl5 to produce chloroalkanes is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand that potassium dichromate(VI) in dilute sulfuric acid can oxidise: i primary alcohols to produce aldehydes (which give a positive result with Benedict’s or Fehling’s solution) if the product is distilled as it forms ii primary alcohols to produce carboxylic acids (which give a positive result with sodium carbonate or sodium hydrogencarbonate) if the reagents are heated under reflux iii secondary alcohols to produce ketones In equations, the oxidising agent can be represented by [O].

Use —potassium dichromate(vi) in dilute sulfuric acid can oxidise: i primary alcohols to produce aldehydes (which give a positive to connect the rule to the data and decision in the question.

This matters because —potassium dichromate(vi) in dilute sulfuric acid can oxidise: i primary alcohols to produce aldehydes (which give a positive determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —potassium dichromate(vi) in dilute sulfuric acid can oxidise: i primary alcohols to produce aldehydes (which give a positive to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Potassium dichromate(VI) in dilute sulfuric acid can oxidise: i primary alcohols to produce aldehydes (which give a positive is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Understand, the following techniques in the preparation and purification of a liquid organic compound: i heating under reflux ii extraction with a solvent using a separating funnel iii distillation iv drying with an anhydrous salt v boiling temperature determination.

Use —understand, the following techniques in the preparation and purification of a liquid organic compound: i heating under to connect the rule to the data and decision in the question.

This matters because —understand, the following techniques in the preparation and purification of a liquid organic compound: i heating under determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —understand, the following techniques in the preparation and purification of a liquid organic compound: i heating under to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Understand, the following techniques in the preparation and purification of a liquid organic compound: i heating under is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

CORE PRACTICAL 7 The oxidation of propan-1-ol to produce propanal and propanoic acid.

Use —core practical 7 the oxidation of propan-1-ol to produce propanal and propanoic acid to connect the rule to the data and decision in the question.

This matters because —core practical 7 the oxidation of propan-1-ol to produce propanal and propanoic acid determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —core practical 7 the oxidation of propan-1-ol to produce propanal and propanoic acid to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —CORE PRACTICAL 7 The oxidation of propan-1-ol to produce propanal and propanoic acid is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular ion and fragmentation patterns.

Use —interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular to connect the rule to the data and decision in the question.

This matters because —interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Interpret data from mass spectra to suggest possible structures of simple organic compounds using the m/z of the molecular is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

Be able to use infrared spectra, or data from infrared spectra, to deduce functional groups present in organic compounds, and predict infrared absorptions, given wavenumber data, due to familiar functional groups including: i C–H stretching absorptions in alkanes, alkenes and aldehydes ii C=C stretching absorption in alkenes iii O–H stretching absorptions in alcohols and carboxylic acids iv C=O stretching absorptions in aldehydes, ketones and carboxylic acids v C–X stretching absorption in halogenoalkanes vi N-H stretching absorption in amines.

Use —infrared spectra, or data from infrared spectra, to deduce functional groups present in organic compounds, and predict to connect the rule to the data and decision in the question.

This matters because —infrared spectra, or data from infrared spectra, to deduce functional groups present in organic compounds, and predict determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —infrared spectra, or data from infrared spectra, to deduce functional groups present in organic compounds, and predict to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —Infrared spectra, or data from infrared spectra, to deduce functional groups present in organic compounds, and predict is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.

CORE PRACTICAL 8 Analysis of some inorganic and organic unknowns.

Use —core practical 8 analysis of some inorganic and organic unknowns to connect the rule to the data and decision in the question.

This matters because —core practical 8 analysis of some inorganic and organic unknowns determines what can be inferred or chosen; begin with the stated conditions and keep the conclusion tied to the evidence.

Example: apply —core practical 8 analysis of some inorganic and organic unknowns to one small, clearly defined case, show the key step or comparison, and explain the result in words.

Boundary: —CORE PRACTICAL 8 Analysis of some inorganic and organic unknowns is not a universal recommendation. Check the syllabus scope, assumptions, units and the limits of the evidence before generalising.