What’s New in Chemical Education?

Camilo Castrillon-Toro & Jason Sonnenberg
Wolfram|Alpha Chemistry Team

(RowDefault[, (Spacer1), , (Spacer1), ])  #WolframTechConf

Abstract

Recent and upcoming features of Wolfram|Alpha (W|A), Wolfram|Alpha Notebook Edition (WANE) and the Wolfram Language (WL) related to chemical education are discussed. These features include expanded Step-by-Step support, improved free form input, new built-in functions for chemical conversion and new Wolfram Function Repository submissions. Example activities and educator resources are highlighted.

Tools for Chemical Education

Wolfram|Alpha - Named Chemical Reactions

TabView[#->WolframAlpha[#]&/@{
"Friedel-Crafts Alkylation",
"Diels-Alder Reaction"
},ImageSize->Automatic
]

Wolfram|Alpha - Step-by-Step Content

TabView[Replace[#,Rule[x_,y_]:>x->WolframAlpha[y]]&/@{
"Ionic Reactions"->"total ionic equation BaCl2(aq) + Na2SO4(aq) -> BaSO4(s) + NaCl(aq)",
"Property Comparisons"->Sequence["Lithium chemical, technetium fluoride, tritium deuteride, SMILES [2H]O(H)[H+] molar mass",IncludePods->{"Input","Result"},AppearanceElements->{"Pods"}],
"Quantity Arithmetic"->Sequence["1.355 kJ/mol + 300 J/mol",IncludePods->{"Input","Result","UnitConversion","ComparisonAsActivationEnergy"},AppearanceElements->{"Pods"}]
},ImageSize->Automatic
]

Wolfram|Alpha - Biochemistry Calculators

TabView[Replace[#,Rule[x_,y_]:>x->WolframAlpha[y]]&/@{
"DNA Mass to Moles"->"DNA mass to moles",
"DNA Concentration to Mass Fraction"->"DNA concentration to mass fraction"
},ImageSize->Automatic]

Wolfram|Alpha - Error Propagation Preview

TabView[{
"Isotopic Mass"->,
"Chemical Quantities"->WolframAlpha["5.125 +- 0.0005 g of S8"],
"Chemical Conversions"->WolframAlpha["convert 5 +- 0.01 mL of 1.5 +- 0.005 mM potassium hydroxide to mg of potassium hydroxide"]
},ImageSize->Automatic]

Wolfram|Alpha Notebook Edition

New Functions

Chemical formulas

Chemical conversion with error propagation

Wolfram Function Repository Support

IUPAC names

Molecule value plots

Improved Natural Language

Two-dimensional plots

Three-dimensional plots

Exploring Atomic Electron Representations

Prerequisite Concepts

Atomic electron configurations, the Aufbau principle, the periodic table, atomic orbital diagrams, Lewis symbols

Learning Objectives

Predict which orbitals contain the outermost electrons with the highest energy using the periodic table

Check that electron configurations have accounted for all electrons

Relate atomic electron configurations to the corresponding Lewis symbol

Relate atomic orbital energy to electron configurations and orbital diagrams

Identify and explain how electron configurations and atomic orbital energy are communicated in various text and graphical forms

American Chemical Society Committee on Professional Training Standards

4.3 - Computational Capabilities and Software

5.2 - Introductory or General Chemistry (atomic structure, electron configurations, Lewis symbols)

7.4 Communication Skills (chemical representations)

Academic Integrity

By typing my name below, I acknowledge awareness of and adherence to the policies on academic integrity. Furthermore, I certify that the submitted work is entirely my own. I pledge to neither give nor receive any unauthorized assistance on this activity.

Enter full name here.

Activity

Let's explore the various ways information about the electrons in an atom are communicated. Start by locating your periodic table:

Look up the atomic symbol for tin and the number of electrons in one tin atom. What is another name for the number of electrons in a neutral atom?

Type your answer here using full sentences with correct grammar and spelling.

Based on the block of the periodic table containing tin, predict where the outermost electrons with the highest energy are located in a tin atom.

Type your answer here using full sentences with correct grammar and spelling.

Determine if your previous prediction was correct using the full electron configuration for tin. Describe one mathematical way to check that all the electrons in tin were assigned to atomic orbitals.

Type your answer here using full sentences with correct grammar and spelling.

Electron configurations are more commonly written in an abbreviated form using the atomic symbol of a noble gas in square brackets. The Lewis symbol for an atom is a graphical presentation of information about the electrons. Compare the full electron configuration, abbreviated electron configuration and Lewis symbol for tin. What information is lost or gained in each representation?

Type your answer here using full sentences with correct grammar and spelling.

Orbital diagrams are another way to communicate atomic electron information graphically. Use the query “show steps tin orbital diagram” to learn how to construct an orbital diagram for tin. What is the best graphical representation of the abbreviated electron configuration: a Lewis symbol or the atomic orbital diagram? Explain your reasoning.

Type your answer here using full sentences with correct grammar and spelling.

Use the Electron Configuration Browser to investigate the electron configurations of lithium, technetium and thorium. Compare the orbital diagram for tin to the orbital diagrams in the Electron Configuration Browser. If the information contained in the diagrams differs, explain what is lost or gained. Which diagram is the best representation? Defend your choice using chemical concepts and terminology.

Type your answer here using full sentences with correct grammar and spelling.

Wolfram Language - New Functions

chemFunc={{ApplyReaction,13.1},{Atom,12},{AtomCount,12},{AtomLabels,13},{AtomLabelStyle,13},{AtomList,12},{Bond,12},{BondCount,12},{BondLabels,13},{BondList,12},{BondQ,12},{ChemicalConvert,13.1},{ChemicalFormula,13},{ChemicalInstance,13.1},{ChemicalReaction,13},{ConnectedMoleculeComponents,12},{ConnectedMoleculeQ,12},{FindIsomers,13},{FindMoleculeSubstructure,12},{Molecule,12},{MoleculeAlign,12.3},{MoleculeContainsQ,12},{MoleculeDraw,12.2},{MoleculeEquivalentQ,12},{MoleculeFreeQ,13},{MoleculeGraph,12},{MoleculeMatchQ,13},{MoleculeMaximumCommonSubstructure,12.3},{MoleculeModify,12},{MoleculeName,12.3},{MoleculePattern,12},{MoleculePlot,12},{MoleculePlot3D,12},{MoleculeProperty,12},{MoleculeQ,12},{MoleculeRecognize,12.1},{MoleculeSubstructureCount,12.3},{MoleculeValue,12},{PatternReaction,13.1},{ReactionBalance,13},{ReactionBalancedQ,13}};
GraphicsRow[{
WordCloud[{{AtomLabels,2},{AtomLabelStyle,1},{BondLabels,2},{ChemicalFormula,3},{ChemicalReaction,3},{FindIsomers,4},{MoleculeFreeQ,1},{MoleculeMatchQ,1},{ReactionBalance,3},{ReactionBalancedQ,1},{ApplyReaction,5},{ChemicalConvert,5},{ChemicalInstance,4},{PatternReaction,4}}],
With[{version=Length/@GroupBy[SortBy[chemFunc,Last],Last]},
BarChart[Accumulate[Values[version]],ChartLabels->Keys@version,ChartStyle->"DarkRainbow",PlotLabel->Style["Total Chemistry Functions",Bold,FontSize->20]]
]
}, ImageSize->1100]

Wolfram Language - New Functions

Chemical Formulas

ChemicalFormula["UO2(H2O)+2"]

Chemical Conversions with Error Propagation

chem=ChemicalInstance[(Entity["barium sulfate", Entity["Chemical","BariumSulfate"], "Entity[\"Chemical\", \"BariumSulfate\"]", "chemical"]),(Quantity[((Around[1.6700, 0.0005])), "g", grams, "Grams"])];
ChemicalConvert[chem,"Millimoles"]

Chemical Reactions with Balancing

rxn=ChemicalReaction["Fe^2+ + [Cr2O7]^2- + H+ -> Fe+3 + Cr+3 + H2O"];
ReactionBalance[rxn]["EquationDisplay"]

Wolfram Language - New Functions

Chemical Synthesis using PatternReaction & ApplyReaction

Options[ReactionView]=Join[{ChemicalFormula->True,MoleculePlot->True},Options[Graph]];
ReactionView[rxn_PatternReaction,{limiting_Molecule,excess_Molecule},n_Integer:1,opts:OptionsPattern[]]:=Module[
{mkArrow,button,edges,products,rxnGraph,rxnStep,tool},
{button,tool}=If[OptionValue[MoleculePlot],{MoleculePlot,MoleculePlot3D},{MoleculePlot3D,MoleculePlot}];
mkArrow=Function[e,Labeled[e,Tooltip[Button[excess["HillFormula"],CopyToClipboard[excess]],tool[excess]]],Listable];
rxnStep=Function[reactant,Flatten[ApplyReaction[rxn,{reactant,excess},All]],Listable];
edges=EdgeList[NestGraph[rxnStep[#]&,limiting,n]];
If[MatchQ[edges,{}],Return[Missing["NoReaction"],Module]];
rxnGraph=Graph[
If[OptionValue[ChemicalFormula],mkArrow[edges],edges],
VertexShape->Map[#->Tooltip[Button[button[#],CopyToClipboard[#]],tool[#]]&,DeleteDuplicates[Flatten[List@@@edges]]],
GraphLayout->If[Length[edges]==1,{"LayeredDigraphEmbedding","Orientation"->Left}, Automatic],VertexSize->Large
];
vl=Transpose[{Range[VertexCount[rxnGraph]],VertexList[rxnGraph]}];
rxnGraph=IndexGraph[rxnGraph];
products=Select[Gather[vl,MoleculeMatchQ[Last[#1],Last[#2]]&][[All,All,1]],Length[#]>1&];
SimpleGraph[VertexContract[rxnGraph,products],FilterRules[{opts},Options[Graph]]]
]
patternAlkene=MoleculePattern[{"C", "C"},{Bond[{1,2},"Double"]}];
patternHX=MoleculePattern[{"H",Alternatives["Cl","Br","I"]},{Bond[{1,2},"Single"]}];
patternHalogenatedAlkane=MoleculePattern[{"C","C",Alternatives["Cl","Br","I"],"H"},{Bond[{1,2},"Single"],Bond[{1,3},"Single"],Bond[{2,4},"Single"]}];
atomMapping={
{1,1}->{1,1}, (* atom one in the first reactant (C=C) becomes the first atom in the product *)
{1,2}->{1,2}, (* atom two in the first reactant (C=C) becomes the second atom in the product *)
{2,1}->{1,4}, (* atom one in the second reactant (HBr) becomes the fourth atom in the product *)
{2,2}->{1,3}  (* atom two in the second reactant (HBr) becomes the third atom in the product *)
};
hydrohalogenation=PatternReaction[{patternAlkene,patternHX}->{patternHalogenatedAlkane},atomMapping];
Manipulate[
ReactionView[
hydrohalogenation,{alkene,halide},n,ChemicalFormula->formula,ImageSize->Full
],
Row[
{
Control[{
{alkene,Molecule[(Entity["ethylene", Entity["Chemical","Ethylene"], "Entity[\"Chemical\", \"Ethylene\"]", "chemical"])],"Alkene:"},
{
Molecule[(Entity["ethylene", Entity["Chemical","Ethylene"], "Entity[\"Chemical\", \"Ethylene\"]", "chemical"])]-> "ethene",
Molecule[(Entity["propylene", Entity["Chemical","Propylene"], "Entity[\"Chemical\", \"Propylene\"]", "chemical"])]->"propylene",Molecule[(Entity["1,4-hexadiene", Entity["Chemical","1,4Hexadiene"], "Entity[\"Chemical\", \"1,4Hexadiene\"]", "chemical"])]->"1,4-hexadiene"
},
ControlType->PopupMenu
}],
Control[{
{halide,Molecule[(Entity["hydrogen iodide", Entity["Chemical","HydrogenIodide"], "Entity[\"Chemical\", \"HydrogenIodide\"]", "chemical"])],"Hydrogen halide:"},
{
Molecule[(Entity["hydrogen chloride", Entity["Chemical","HydrogenChloride"], "Entity[\"Chemical\", \"HydrogenChloride\"]", "chemical"])]->"hydrogen chloride",Molecule[(Entity["hydrogen bromide", Entity["Chemical","HydrogenBromide"], "Entity[\"Chemical\", \"HydrogenBromide\"]", "chemical"])]->"hydrogen bromide",Molecule[(Entity["hydrogen iodide", Entity["Chemical","HydrogenIodide"], "Entity[\"Chemical\", \"HydrogenIodide\"]", "chemical"])]->"hydrogen iodide"
},
ControlType->PopupMenu
}],
Control[{{n,1,"Reaction Step:"},Range[2]}],
Control[{{formula,True,"Chemical Formulas:"},{True,False}}]
},Spacer[10]
],
SaveDefinitions->True
]

Mathematica & Wolfram Language
Fast Introduction for Chemistry Students

Getting Started

Electronic Notebooks

Entering Input

Fractions & Decimals

Variables & Functions

Chemistry 101

Chemical Representations

Atoms

Chemical Formulas

Molecules

DNA, RNA & Peptides

Chemical Entities

Data Love

Measured Data

Quantities & Units

Topical Survey

Visualizing Molecules

Chemical Conversions

Quantum Chemistry

Chemical Reactions

Stoichiometry

Chemical Synthesis

Group Theory

Chemical Informatics

Further Explorations

The Wolfie Stone

Continue Reacting

Useful Links

Grid[
Replace[
#,
{label_,address_}:>{ImageResize[BarcodeImage[address,"QR"],100],Spacer[10],Style[Hyperlink[label,address],FontSize->30]}
]&/@
{
{
"Wolfram Core Areas - Chemistry",
"https://www.wolfram.com/language/core-areas/chemistry/"
},
{
"Online Dilution Calculator: Chemistry Solvers",
"https://www.wolframalpha.com/calculators/dilution-calculator"
},
{
"Fast Introduction for Chemistry Students","https://www.wolframcloud.com/obj/WolframChemistryTeam/Published/FastIntro/FastIntro.nb"
},
{
"Wolfram Chemistry Resources",
"https://www.wolframcloud.com/obj/WolframChemistryTeam/Published/ChemistryResources.nb"
}
},
Alignment->Left,Spacings->{Automatic, 3}
]