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Chemistry II - Stereochemistry

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Section 1

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While arranging a molecule within three dimensional space to determine the stereochemistry, what should be done?

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Mar 1, 2020

Cards (13)

Section 1

(13 cards)

While arranging a molecule within three dimensional space to determine the stereochemistry, what should be done?

Front

The lowest priority should be placed in the back. Thus, the line of sight should be "down" this bond with it at the back of the molecule.

Back

In terms of isomers, stereoisomers are more similar. What distinction do stereoisomers have between each other?

Front

They have different orientation of atoms (wedges and dashes in space) around a single atom

Back

What do conformational isomers arise from? What are used to demonstrate these?

Front

Different varieties of rotation around a single bond (sigma) can create differing levels of strain Newman projections

Back

In a Newman projection, what does the gauche conformation arise from? What does the anti-gauche conformation arise from?

Front

Gauche arises from the largest groups are 60 degrees apart. Anti-gauche is when the largest groups are 180 degrees apart.

Back

T/F Achiral objects have mirror images that can be superimposed always

Front

T

Back

T/F Diasteromers have identical physical and chemical properties, much like enantiomers.

Front

F These do NOT have identical properties!

Back

What do structural isomers have in common? Are these the most or least similar isomers?

Front

They have the same molecular weight and the same formula These are the LEAST similar isomers

Back

T/F The two conformations of configurational isomers are diastereomers and enantiomers. Only enantiomers rotate plane polarized, though.

Front

F Both do since both are chiral, and the definition of chirality is the ability to rotate plane polarized light.

Back

Cyxlohexanes can be either fairly stable or unstable depending on ring strain. Angle, torsional, and non-bonding strain all contribute to this. What are these types of strain?

Front

Angle is when bond angles exceed optimal angles Torsional is when cyclic molecules adopt eclipsed conformations Non-bonding is when non-adjacent molecules sterically hinder each other (steric strain)

Back

A racemic mixture contains an equal mixture of (+) and (-) enantiomers. What would the half that rotates light clockwise be designated as? Counterclockwise?

Front

Clockwise (+) Counterclockwise (-)

Back

A molecule with 4 chiral centers has how many possible stereoisomers?

Front

2^4 16

Back

What is the only situation in which a molecule may have chiral centers but not rotate plane polarized light?

Front

It is a MESO compound, thus it has an internal plane of symmetry.

Back

How are chiral molecules related in their reactivity?

Front

They are identical in ALL ways except their ability to rotate plane polarized light. Thus, they may react differently in chiral environments.

Back