Organic Chem Basics

Organic 1 – the basics

What to expect from Organic 1

Click here for a glossary of terms used in Organic Chemistry

Having taken two semesters of General Chemistry you should have a firm grasp of the organization of the Periodic Table and how the trends found within help us to understand how and why atoms bond with each other. Organic Chemistry begins with a review of concepts such as electronegativity, hybridization, shape, and valence so students need to be happy with these ideas from the beginning. Much of this is discussed on the Preparation page.

Organic 1 then progresses with a more in-depth look and Acid-Base chemistry and how chemical concepts may be applied to predict products and the position of an equilibrium in a reaction. This serves as an introduction to reactivity and mechanism. The rest of Organic 1 is spent building towards Chemical Synthesis by studying ideas such as conformation and stereochemistry, which leads to in-depth study of the reactivity of alcohols, alkyl halides, alkynes and alkanes.

Below is a rough guide to the major ideas to be discussed and conquered in Organic Chemistry 1. The first tab in each block features a YouTube summary of the topic; the second tab contains a short quiz on the material discussed.

Shape and Structure

The models below represent examples of the three main geometries encountered in Organic Chemistry, namely tetrahedral (in methane, ethane, and propane), trigonal planar (in ethylene), and linear (in acetylene).

Methane (sp3 C, tetrahedral)

Ethane (sp3 C, tetrahedral)

Propane (sp3 C, tetrahedral)

Ethylene (sp2 C, trigonal planar)

Acetylene (sp C, linear)

Hybridization Quiz

Practice spotting hybridization patterns

1 / 10

What hybridization is Nitrogen here?

2 / 10

How many sp2 hybrid atoms in this molecule?

3 / 10

How many sp hybrid atoms here?

4 / 10

What hybridization patterns for the Oxygen atoms here?

5 / 10

How many sp2 Carbon atoms here?

6 / 10

What shape are sp atoms typically?

7 / 10

How many sp3 Carbon atoms here?

8 / 10

What shape is a typical sp2 atom?

9 / 10

What shape is a an sp3 atom typically?

10 / 10

How many sp2 Carbon atoms here?

Your score is

The average score is 81%

0%

Functional Groups

/10

Functional Group Quiz

Practice identifying Organic functional groups

1 / 10

Which functional groups are present here?

2 / 10

Name the functional groups present here.

3 / 10

Which functional groups are in this compound?

4 / 10

Name the functional groups present here.

5 / 10

What functional groups are contained here?

6 / 10

Which functional groups does this molecule feature?

7 / 10

Identify any functional groups.

8 / 10

Which functional groups?

9 / 10

Which functional groups are in this molecule?

10 / 10

Which functional groups are present?

Your score is

0%

Examples of alkyl halide functional groups are collected below as moveable models; green atoms = F or Cl, red = O, blue = N, orange = Br, purple = I, yellow = S.

1-Chorobutane (1o alkyl halide)

2-Fluorohexane (2o alkyl halide)

Iodocyclopentane (2o alkyl halide)

1-Bromo-1-methylcyclohexane (3o halide)

Examples of the alkene functional group are collected below as moveable models; green atoms = F or Cl, red = O, blue = N, orange = Br, purple = I, yellow = S.

trans-2-Butene (disubstituted)

Cyclohexene (disubstituted)

1,2-Dimethylcyclopentene (disubstituted)

2,3-Dimethylacrylonitrile (trisubstituted)

Examples of the alkyne functional group are collected below as moveable models; green atoms = F or Cl, red = O, blue = N, orange = Br, purple = I, yellow = S.

1-Hexyne (terminal)

2-Pentyne (internal)

Cyclononyne (internal)

Di-t-butylacetylene (internal)

Examples of the alcohol functional group are collected below as moveable models; green atoms = F or Cl, red = O, blue = N, orange = Br, purple = I, yellow = S.

Cyclopentanol (secondary)

1-Octanol (primary)

Glycerol (primary & secondary)

Isopropanol (secondary)

Examples of the ether functional group are collected below as moveable models; green atoms = F or Cl, red = O, blue = N, orange = Br, purple = I, yellow = S.

Diethyl ether (acyclic)

Tetrahydrofuran (cyclic)

Furan (acyclic)

Methylphenyl ether (acyclic)

Examples of the thiol functional group are collected below as moveable models; green atoms = F or Cl, red = O, blue = N, orange = Br, purple = I, yellow = S.

Butanethiol

Thiophenol

beta-Mercaptoethanol

Glutathione(H)

Dipropylsulfide

Tetrahydrothiophene

Thiopyran

Thietane

Benzene

Naphthalene

Aspirin

Phenylalanine

Acetaldehyde

Butyraldehyde

Benzaldehyde

(E)-Cinnamaldehyde

Acetone

Benzophenone

Cyclohexanone

Camphor

Acetic acid

Benzoic acid

Phthalic acid

Alanine

Propionyl chloride

Benzoyl chloride

Adipoyl chloride

Acetyl fluoride

Acetic anhydride

Benzoic anhydride

Maleic anhydride

Phthalic anhydride

Ethyl acetate

Methyl benzoate

Butyl propanoate

Glycerol decanoate

Acetamide

Caprolactam

N,N-Dimethylformamide

Penicillin G

Methylamine (primary)

Triethylamine (tertiary)

Cadaverine (primary)

Piperidine (secondary)

Resonance Structures

Resonance Quiz

Test your knowledge of resonance patterns

1 / 10

The following charge can delocalize.

2 / 10

Which resonance structure is more significant and why?

3 / 10

What, if anything, is wrong with the following structure?

4 / 10

Which, if either, resonance structure is more significant?

5 / 10

What is fundamentally wrong with this resonance structure?

6 / 10

Which resonance structure is more significant and why?

7 / 10

Can this charge delocalize? Why or why not?

8 / 10

Which structure is more significant and why?

9 / 10

Which structure is invalid and why?

10 / 10

Which structure is more significant and why?

Your score is

The average score is 70%

0%

Allyl carbocation

Acids and Bases

Acid-Base Quiz

Check your knowledge on Acid-Base chemistry

1 / 10

What is the approximate pKa for this molecule?

2 / 10

Which side of the equation is favoured and why?

3 / 10

What is the approximate pKa for this molecule?

4 / 10

Which side of the equation is favoured and why?

5 / 10

What is the approximate pKa for this molecule?

6 / 10

Which side of the equation is favoured and why?

7 / 10

What is the approximate pKa for this molecule?

8 / 10

Which side of the equation is favoured and why?

9 / 10

What is the approximate pKa for this molecule?

10 / 10

Which side of the equation is favoured and why?

Your score is

The average score is 70%

0%

Alkane Nomenclature

Alkane Names Quiz

Test how much you know about Alkane names

1 / 10

Which name matches the structure of this molecule?

2 / 10

Choose name that best matches this molecule.

3 / 10

Which name applies to this molecule?

4 / 10

Which name applies to this molecule?

5 / 10

Which name best matches this molecule?

6 / 10

Which is the proper name for this molecule?

7 / 10

The correct name for this molecule?

8 / 10

How would you name this molecule?

9 / 10

Which is the correct name for this molecule?

10 / 10

Which name matches this structure?

Your score is

The average score is 57%

0%

Conformational Analysis

An overview of Acyclic Conformation is linked here; Cyclohexane Conformation here.

Conformation Quiz

Check on what you know about Conformation

1 / 10

Which statement best describes this picture?

2 / 10

Which description matches this image?

3 / 10

Which statement best matches the structure?

4 / 10

Which name best matches this structure?

5 / 10

Which is the correct description of this structure?

6 / 10

Choose the best description for this conformation.

7 / 10

Choose the best description for this molecule.

8 / 10

Choose the best description for this molecule.

9 / 10

Which is the best description of this molecule?

10 / 10

Which is the correct description of this structure?

Your score is

The average score is 60%

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Chirality and Configuration

Configuration Quiz

Test yourself on Configuration basics

1 / 10

Which description matches this molecule best?

2 / 10

How are these molecules related?

3 / 10

The configurations of the chiral centres?

4 / 10

What is the relationship between these molecules?

5 / 10

Which description matches this molecule best?

6 / 10

What are the configurations of the chiral centres here?

7 / 10

What is the configuration of the chiral centre here?

8 / 10

What is the stereochemical identity of this molecule?

9 / 10

What is the configuration of this molecule?

10 / 10

The most appropriate name for this compound?

Your score is

The average score is 68%

0%

Reactivity Basics

Reactivity

Reactivity Quiz

Quiz your self on Reactivity basics

1 / 10

Which molecule is less stable and why?

2 / 10

Which species is more stable and why?

3 / 10

Which carbocation is more stable and why?

4 / 10

Which molecule is more favoured entropically and why

5 / 10

Which statement best matches the entropic change here and why?

6 / 10

Which of these isomers is more stable and why?

7 / 10

Which of these species is more reactive and why?

8 / 10

Which side of the equation is more stable and why?

9 / 10

Which isomer is more stable and why?

10 / 10

Which molecule is more stable and why?

Your score is

The average score is 65%

0%

Substitution and Elimination

SN/E Quiz

Quiz on Substitution and Elimination reactions.

1 / 10

Which of the following solvents is best for SN1 reactions? Choose one.

2 / 10

What is the expected major product of reaction with NaBr?

3 / 10

What major product is formed when this molecule reacts with KOt-Bu?

4 / 10

Which molecule reacts faster in E2 with a small base and why?

5 / 10

Which alkene is more stable and why?

6 / 10

Which molecule reacts faster in SN2 reactions and why?

7 / 10

Which solvent is most appropriate for fast SN2 reactions? Choose one option.

8 / 10

Which molecule reacts faster in SN1 reactions and why?

9 / 10

Which of the following is true of all SN2 reactions? Choose one.

10 / 10

Which molecule reacts faster in SN2 reactions and why?