optical isomerism

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8 Terms

1
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what is optical isomerism? when does it occur?

  • form of stereoisomerism

  • occurs as a result of chirality in molecules

  • limited to molecules w/ a single chiral centre

<ul><li><p>form of stereoisomerism </p></li><li><p>occurs as a result of chirality in molecules</p></li><li><p>limited to molecules w/ a single chiral centre </p></li></ul><p></p>
2
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what is a chiral C?

C with 4 diff groups attached

<p>C with 4 diff groups attached </p>
3
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what is an enantiomer?

  • isomers where groups are arranged around chiral Cs differently

  • are non superimposable mirror images of each other

<ul><li><p>isomers where groups are arranged around chiral Cs differently</p></li><li><p>are non superimposable mirror images of each other </p></li></ul><p></p>
4
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what is a racemic mixture/racemate?

mixture of equal amounts of enantiomers

5
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how are enantiomers similar and how do they differ?

  • have identical chemical and physical properties

  • but differ in their effect on plane polarised light (as they are optically active) and their reactions w/ other chiral molecules

6
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describe the effect of enantiomers on plane polarised light:

  • enantiomers are optically active - rotate plane polarised light

  • plane polarised light typically only vibrates in one direction

  • the 2 enantiomers will rotate the plane of polarised light in opposite directions (i.e. clockwise and anticlockwise)

<ul><li><p>enantiomers are optically active - rotate plane polarised light</p></li><li><p>plane polarised light typically only vibrates in one direction</p></li><li><p>the 2 enantiomers will rotate the plane of polarised light in opposite directions (i.e. clockwise and anticlockwise) </p></li></ul><p></p>
7
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give and explain the rotational effect on plane polarised light of a racemic mixture:

  • overall effect of zero

  • opposing rotations cancel out

  • so racemic mixture is optically inactive

8
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explain how reactions involving carbonyl groups often produce racemic mixtures:

  • carbonyl is planar around functional group

  • ∴ attack from either either side =lly likely

  • giving = amounts of both enantiomers

<ul><li><p>carbonyl is planar around functional group</p></li><li><p><span><span>∴ attack from either either side =lly likely</span></span></p></li><li><p><span><span>giving = amounts of both enantiomers</span></span></p></li></ul><p></p>