Organic Chemistry 1 Complete Set

This is the complete set of flashcards covering all of semester 1 of organic chemistry module. The flashcards are made from details on slides and edited to keep updated after lectures.

Structure determination

How to find out the structure of new compounds.

Theoretical Organic Chemistry

How to understand structures in terms of atoms and electrons that bind them together.

Reaction mechanisms

How to find out how molecules react with each other and how to predict their reactions.

Synthesis

How to design and make new molecules.

Biological Chemistry

How to find out what Nature does and how the structures of biologically active molecules are related to what they do.

Draw a methyl cation:

Draw a methyl anion:

Draw a methyl radical:

Draw n-butanol:

Draw sec-butanol:

Draw tert-butanol:

Draw 2,2-dimethylpropan-1-ol:

What is General Formula for propan-1-ol?

C_nH_2n+1OH

What is Empirical Formula for propan-1-ol?

C₃H₈O

What is Molecular Formula for propan-1-ol?

C₃H₇OH

What is the structural/condensed formula for propan-1-ol?

CH₃CH₂CH₂OH

Draw displayed formula for propan-1-ol:

Draw skeletal formula for propan-1-ol:

Draw Perspective projection Staggered, Ethane style:

Draw Perspective projection Eclipsed, Ethane style:

Draw Newman projection Staggered, Ethane style:

Draw Newman projection Eclipsed, Ethane style:

Draw Fischer projection, Ethane style:

Draw Sawhorse projection Staggered, Ethane style:

Draw Sawhorse projection Eclipsed, Ethane style:

List abbreviations for alkyl groups up to (including) butyl:

Me, Et, Pr, Bu

How can you form a propyl group from propane? Draw an example for the formation of an isopropyl group:

Remove a hydrogen from either a secondary or primary carbon on propane.

Draw isopropyl chloride:

Draw isopentyl alcohol:

Draw isobutylamine:

Draw isopropyl bromide:

Draw isobutyl group:

Draw sec-butyl group:

Draw tert-butyl group:

What is Ph an abbreviation of?

Phenyl

What is Bn an abbreviation of?

Benzyl

What is Ac an abbreviation of?

Acetyl

Draw Vinyl molecule:

Draw Allyl molecule:

What is R an abbreviation of?

Any group

What is Ar an abbreviation of?

Aromatic group

What is i-Pr an abbreviation of?

isopropyl

What is t-Bu an abbreviation of?

tert-butyl

What is X an abbreviation of?

Halide

Draw the 3D structures for CH₂BrCl with different perspectives:

Draw the 3D structures for CH₂ClCH₂Br with different perspectives:

Draw the standard tetrahedral 3D skeletal model, which has hash and wedge bonds:

Define Isomer

Compounds that have the same molecular formula but different structures

What is a constitutional isomer?

Has the same molecular formula, but differ in atom connectivity and possibly functional groups.

What is a configurational isomer?

Has the same molecular formula and atom connectivity, but differs in spatial arrangement of atoms.

What are geometric isomers?

Compounds that differ in how their substituents are arranged around the double bond. Geometric isomers can be separated,

What are cis isomers?

Cis isomers have the chain of the same side of the double bond/ring.

What are trans isomers?

Trans isomers have the chain on opposite sides of the double bond/ring.

What are the Cahn-Ingold-Prelog Rules?

1) Assign priority to substituents according to atomic number.

2) If two substituents have the same atomic number, go to the next set of atoms in line.

3) If the highest priority groups are on opposite sides, the isomer is E.

4) If the highest priority groups are on the same side, the isomer is Z.

How would a C-C triple bond be treated according to Cahn-Ingold Prelog rules?

Treated as CCC

Describe rotation around a single bond:

Electron density is in the middle of two atoms. The overlap of orbitals is undisturbed by rotation around the bond. This allows for a variety of conformations of a molecule.

Why is the Newman projection useful?

The best way to judge the stability of the different conformations of a molecule.

Describe the difference in energy between staggered and eclipsed conformations:

• The steric hinderance and therefore steric strain is greater when the electron clouds of large substituents overlap with each other.

• Greater repulsion means more energy is required to keep the molecule stable, so the molecule is generally more stable when staggered and less stable when eclipsed.

What is the meaning of syn-periplanar, synclinal, gauche, anticlinal and anti-periplanar?

• Syn-periplanar (eclipsed) = both of the bulkiest substiuents are eclipsing each other.

• Synclinal/gauche (staggered) = both of the bulkiest groups are 60 degrees apart from each other.

• Anti-clinal (eclipsed) = both of the bulkiest groups are 120 degrees apart from each other.

• Anti-periplanar (staggered) = both of the bulkiest groups are 180 degrees apart (staggered formation)

Draw the anticlinal conformation for butane in Newman projection:

Draw the anti-periplanar conformation of butane as a Newman projection:

Draw the syn-periplanar conformation of butane as a Newman projection:

Draw the synclinal/gauche conformation of butane as a Newman projection:

Draw the butane conformations on an energy diagram showing the positions and Newman projections of each conformation:

Can conformers be separated?

Pure conformers can be observed and predicted, but cannot be isolated in most cases, because the molecules are constantly rotating through all the possible conformations.

Name this structure:

2-methylpentane

Draw the structure 3-ethyl-3-methylhexane:

Name the structure:

3,3-dimethylhexane

Draw the structure 4-ethyl-3,3-dimethylheptane

Name this structure:

4-ethyl-5-isopropyloct-2-ene

Draw this molecule 6-(1,2-dimethylpropyl)-4-propyldecane:

Name this structure:

2,3-dimethyl-5-(2-methylbutyl)decane

Name this structure:

1-cyclobutylpentane

Draw the molecule 1-methyl-2-propylcyclopentane:

Name this molecule:

1,1,2-trimethylcyclopentane

Draw the molecule 4-ethyl-2-methyl-1-propylcyclohexane:

Name this molecule:

trans-cyclodecane

Draw the molecule cyclooctene:

Name this molecule:

phenylmethanol

Name this functional group:

Alcohol

Name this functional group:

Ether

Name this functional group:

1,1-diol

Name this functional group:

hemiacetal

Name this functional group:

acetal

Name this functional group:

Aldehyde

Name this functional group:

Ketone

Name this functional group:

Carboxylic acid

Name this functional group:

Acid chloride

Name this functional group:

Acid anhydride

Name this functional group:

Ester

Name this functional group:

Amide

Name this functional group:

Lactone (cyclic ester)

Name this functional group:

Lactam (cyclic amide)

Name this functional group:

Imide

Name this functional group:

Carbamate (urethane)

Name this functional group:

Urea

Name this functional group:

Amines

Name this functional group:

Imine

Name this functional group:

Oxime

Name this functional group:

Hydrazone