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Test Bank for Organic Chemistry 4th Edition by David Klein Chapter 1
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Test Bank for Organic Chemistry 4th Edition by David Klein Chapter 1
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Test Bank for Organic Chemistry 4th Edition by DavidKlein Chapter 1-27
Alkanes - ANSWER - First four alkanes are methane (CH4), Ethane (C2H6),
Propane (C3H8), and Butane (C4H10)
- single Bonded
Alkenes and Alkynes - ANSWER - Contain double and triple bonds respectively.
Alcohols - ANSWER - contain Hydroxyl group (OH)
- suffix ol or hydroxy if a higher priority group is present
- Diols contain two hydroxyl groups.
* Geminal: 2 Hydroxyl groups on the same carbon
* Vicinal: on adjacent carbons
Carbonyl group - ANSWER
Common Names of Aldehydes - ANSWER - suffix al
- Common names include
* formaldehyde for methanal (R = H)
* Acetyldehyde for ethanal ( R = CH3)
* Propionaldehyde for propanal (R = CH3CH2)
Aldehyde vs. Ketones Terminal group - ANSWER - An aldehyde has a terminal
functional group due to the one hydrogen
- Ketone has two alkyl groups so it's never a terminal group.
Naming cyclic Aldehydes - ANSWER
Aldehyde Nomenclature: Methanal - ANSWER Formaldehyde
Aldehyde Nomenclature: Ethanal - ANSWER Acetaldehyde
Aldehyde Nomenclature: Propanal - ANSWER Propionaldehyde
Aldehyde Nomenclature: Butanal - ANSWER Butyraldehyde
Aldehyde Nomenclature: Pentanal - ANSWER Valeraldehyde
Naming Ketones: 2-propanone - ANSWER - Dimethyl ketone
- Acetone
Naming Ketones: 2-butanone - ANSWER - ethylmethylketone
Naming Ketones: 3-oxobutanoic Acid - ANSWER
Naming Ketones: Cyclopentanone - ANSWER
,Common Names for Ketones - ANSWER - suffix one
- Acetone (dimethylketone; 2- propanone) ; smallest ketone; similar as the figure
- 2 pentanone (R= CH3CH2CH2)
3-butene-2-one - ANSWER - Naming ketones
- methylvinylketone
Carboxylic Acids and Derivatives - ANSWER - Contain both carbonyl group C=O and
hydroxyl group (OH)
- most oxidized group that appear on the MCAT
- Suffix: Oic acid
- Methanoic acid (Formic Acid)
- Ethanoic acid (acetic acid)
- Propanoic Acid (Propanoic Acid)
Ester - ANSWER - Carboxylic acid derivative
- OH is replaced with OR, an alkoxy group
Amides - ANSWER - Carboxylic acid derivative
- OH is replaced with an amino group
Anhydrides - ANSWER - Carboxylic acid derivative
- formed by dehydration of 2 carboxylic acids
* Symmetric = same acid
* asymmetric = two different acids
* cyclic = intramolecular reaction of a dicarboxylic acid
Summary of Functional Groups - ANSWER Carboxylic acid > anhydride > Ester >
Amide > Aldehyde > Ketone > Alcohol > alkene or alkyne > alkane
Structural Isomer - ANSWER - Share only a molecular formula
- They have different physical and chemical properties
Conformational Isomer - ANSWER - Same molecule, differ in rotation around single
pi bonds.
Newman's Projection - ANSWER - Anti staggered isomer has the lowest energy
- Staggered isomer has the highest energy
Configurational Isomer - ANSWER - Can be interconverted only by breaking bonds.
- consist of two categories:
* Enantiomers: nonsuperimposable mirror image and thus have opposite
stereochemistry at every chiral carbon.
* Diasteromer: non- mirror image stereoisomers; differ at some but not all chiral
centers. Ex) cis - trans isomers
Diastereomers - ANSWER - non- mirror image configurational isomer.
- differ at some but not all chiral centers. Ex) cis - trans isomers
, Enantiomer - ANSWER - Nearly identical physical properties and chemical
properties
- They rotate plane polarized light in opposite directions and react differently in chiral
environment
Chiral center - ANSWER - 4 different group attach to the central carbon
- lack a plane of symmetry
- not superimposable
Achiral - ANSWER - Superimposable
- line of symmetry
Racemix Mixture - ANSWER - Displays no optical activity
- when both (+) and (-) enantiomers are present in equal concentrations.
- Ex) A solution containing 2M (R)-2-butanol and 2 M (S)-2-butanol
Meso Compound - ANSWER - are essentially the molecular equivalent of a racemic
mixture.
- Racemix: when both (+) and (-) enantiomers are present in equal concentrations,
no optical activity
- Has a plane of symmetry = no optical activity
- overall achiral ( mirror images that can be superimposed) and will not rotate plane
polarized light.
(E) and (Z) Designations of Alkenes - ANSWER - Z : same side
- E: Opposite side
- used for compounds with polysubstituded double bonds.
- Part of relative configuration
(R) and (S) Nomenclature - ANSWER - Used for chiral (stereogenic: 4 different
groups bound to it in a non superimposable image) centers in molecules.
- (R) rotates to the right; clockwise
- (S) rotates to the left; counterclockwise
- Part of relative configuration
Maximum number of stereoisomer - ANSWER
Equation for specific rotation - ANSWER
Single Bonds - ANSWER - Sigma bonds, contains two electrons.
* Permit free rotation
Double Bonds - ANSWER - Contain one sigma bond and one pi bond.
- Pi bonds are created by sharing of electrons between two unhybridized p-orbitals
that align side by side.
- Pi bonds do not permit rotations
Triple Bonds - ANSWER - Contain one sigma bond and two pi bonds.
- Pi bonds do not permit rotations
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