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MCAT Organic Chemistry Exam Questions And Correct Answers

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©THEBRIGHT EXAM STUDY SOLUTIONS 8/22/2024 12:54 PM MCAT Organic Chemistry Exam Questions And Correct Answers Electrostatic Forces - answerThe attractive force between electrons and the nuclei that is responsible for all molecular bonds. Coordinate Covalent Bond - answerOne nucleus donates bot...

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mcat organic chemistry exam questions and correct

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©THEBRIGHT EXAM STUDY SOLUTIONS 8/22/2024 12:54 PM

MCAT Organic Chemistry Exam Questions
And Correct Answers

Electrostatic Forces - answer✔✔The attractive force between electrons and the nuclei that is
responsible for all molecular bonds.

Coordinate Covalent Bond - answer✔✔One nucleus donates both of the electrons in the bond.

Hybridization - answer✔✔sp - 180° - linear

sp2 - 120° - trigonal planar

sp3 - 109.5° - tetrahedral, pyramidal, or bent

dsp3 - 90°, 120° - trigonal-bipyramidal, seesaw, t-shaped, linear

d2sp3 - 90° - octahedral, square pyramidal, square planar

When one or more shape is possible, it is determined by the number and position of the lone
pairs of electrons.

Instantaneous Dipole Moment - answer✔✔Exists in an otherwise nonpolar molecule. Occurs
because the electrons in a bond move about the orbital and at any moment may not be distributed
exactly between the two bonding atoms, even when the atoms are identical.

London Dispersion Forces - answer✔✔Occur between two instantaneous dipoles; the weakest
dipole-dipole force (vs. hydrogen bonds which are the strongest dipole-dipole forces).

Zwitterion - answer✔✔A neutral molecule with a positive and negative electrical charge at
different locations within the molecule at a pH of 7.

, ©THEBRIGHT EXAM STUDY SOLUTIONS 8/22/2024 12:54 PM

Ex: amino acids -> amine group deprotonates the carboxylic acid group.

Isomers - answer✔✔Molecules that have the same molecular formula but are different
compounds.

Conformational Isomers (Conformers) - answer✔✔Not true isomers - different spatial
orientations of the same molecule. At low temperatures, the anti-conformation is the most
common.

Structural Isomers - answer✔✔Have the same molecular formula but different bond-to-bond
connectivity; simplest form of isomer.

Stereoisomers - answer✔✔Two molecules with the same molecular formula and same bond-to-
bond connectivity that are not the same compound. Like conformational isomers but contain at
least one *chiral/stereo center (C bonded to 4 different substituents).

2 types:
- Enantiomers
- Diastereomers

Enantiomers - answer✔✔Stereoisomers that have opposite absolute configurations at EACH
chiral center (mirror images). Cannot be separated by physical means.

When in equal concentrations -> racemic mix.

Resolution = the separation of enantiomers.

Same physical and chemical characteristics except in 2 cases:
1) Reactions with other chiral compounds.
2) Reactions with polarized light.

Diastereomers - answer✔✔Stereoisomers that are not mirror images (are not the same
compound). Can be separated by physical means (crystallization).

Geometric isomer: special type of diastereomer, have different physical properties.

, ©THEBRIGHT EXAM STUDY SOLUTIONS 8/22/2024 12:54 PM

- Cis: has dipole moment -> strong intermolecular forces so has high boiling point; lower
symmetry does not form crystals as easily so has lower melting point; has steric hindrance so has
higher heats of combustion.
- Trans: no dipole moment - lower boiling point, higher melting point, lower heats of
combustion.

--> better to use E (Opposite) and Z (same)

Epimer - answer✔✔Diastereomers that differ at only one chiral center.

Anomers - answer✔✔Two diastereomers formed from a ring closure at an epimeric C.

Anomeric carbon: the chiral carbon of the anomer.

Ex: glucose - anomeric C determines if it's α-glucose or β-glucose.

Meso Compounds - answer✔✔Optically inactive (achiral) molecule with two chiral centers;
have a plane of symmetry between their centers which divides the molecule into halves that are
mirror images of each other.

Absolute Configuration - answer✔✔The only way to absolutely describe a chiral molecule.

R = rectus: right (clockwise)
S = sinister: left (counterclockwise)
*for when H (or any other 4th priority substituent) is on DASHES.

Mirror images of chiral molecules always have opposite absolute configurations.

*Note: retention of configuration does not mean that absolute configuration is retained; it means
that there is no inversion.

# stereoisomers of a chiral molecule = 2^n where n = # of chiral Cs

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MCAT Organic Chemistry Exam Questions And Correct Answers

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