OrganicFallChpt7

OrganicFallChpt7 - Chapter 7 Homework All in-chapter...

Info iconThis preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Chapter 7 Homework All in-chapter problems End of chapter: 24, 26, 29, 36, 39, 41 Extra problems: For the following reactions, identify whether the products you get will be achiral, R, S, cis, or trans? H 3 CO H H 2 , Pt CH 3 H Br H KOC(CH 3 ) 3   HOC(CH 3 ) 3 BH 2 H 2 O 2 , NaOH HBr CH 3 H HO H 2 SO 4 , H 2 O
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Chapter 7: Stereochemistry Stereoisomers Molecules with the same molecular formula, the same connectivity, but different arrangement in space A more specific definition of arrangement in space Chirality Enantiomers • Mirror images of the same compound • Non-superimposable Molecule is chiral if its two mirror-image forms are not superimposable in 3D Achiral • A molecule which is superimposable upon its mirror image A chiral molecule can have only one mirror image
Background image of page 2
Here is 1-bromo-1-flouroethane and its mirror image How can we test for chirality? • Rotate the mirror image 180 degrees on the central carbon • The swivel carbon is the stereogenic center . It is the focal point of any chiral molecule. Easy way to recognize a stereogenic center • If all four groups around the center are different, then it is chiral • If there are two groups which are the same around the central carbon, it is achiral Examples H 3 C H Br F CH 3 H Br F mirror plane CH 3 H Br F 180 degrees H 3 C H Br F
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Moving slide Chirality is common in nature D and L amino acids You need an sp 3 center for chirality The other two hybrid centers cannot be chiral Ring carbons Chiral or achiral? Notice the 4 different groups on that one particular carbon Notice that point of difference counts in chirality. O Br H 1-bromohydrofuran cis-1,2-dimethylcyclohexane
Background image of page 4
Symmetry A plane of symmetry which bisects a molecule will invalidate it as a chiral molecule A plane of symmetry is a mirror plane within the molecule itself. Notice the plane of symmetry, even though it looks as though it has two chiral centers. The plane of symmetry cannot be used to prove chirality, but it can be used to rule out chirality. Properties of Chiral Molecules Optical activity • A pure enantiomer will rotate plane- polarized light Plane polarized light is light which is kept in one plane. Typical light oscillates in all planes, but a polarized light filter will only allow light of one oscillation through 1,2-cis-dimethylcyclobutane
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
• A light detector finds the magnitude of the angle shift of the light the compound rotates
Background image of page 6
Image of page 7
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/27/2008 for the course CHEM 3630 taught by Professor Ruane during the Spring '07 term at Wisc Platteville.

Page1 / 16

OrganicFallChpt7 - Chapter 7 Homework All in-chapter...

This preview shows document pages 1 - 7. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online