Chapter 4

Chapter 4 - Chapter 4: Stereochemistry Introduction To...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Chapter 4: Stereochemistry
Background image of page 1

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

View Full DocumentRight Arrow Icon
Introduction To Stereochemistry Consider two of the compounds we produced while finding all the isomers of C 7 H 16 : 2-methylhexane is superimposable with its mirror image CH 3 CH 3 2-methylhexane 3-methylhexane Me C Me 2-methylhexane Me Me H Bu Me Me H Bu mirror rotate Me Me H Bu H
Background image of page 2
Introduction To Stereochemistry CH 3 CH 3 2-methylhexane 3-methylhexane Et Me H Pr Et Me H Pr mirror rotate C Me 3-methylhexane H Et Me Pr H Consider two of the compounds we produced while finding all the isomers of C 7 H 16 : 3-methylhexane is NOT superimposable with its mirror image
Background image of page 3

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

View Full DocumentRight Arrow Icon
Introduction To Stereochemistry Compounds that are not superimposable with their mirror image are called chiral (in Greek, chiral means "handed") 3-methylhexane is a chiral molecule. Compounds that are superimposable with their mirror image are called achiral . 2-methylhexane is an achiral molecule. An atom (usually carbon) with 4 different substituents is called a stereogenic center or stereocenter . CH 3 CH 3 2-methylhexane 3-methylhexane Consider two of the compounds we produced while finding all the isomers of C 7 H 16 :
Background image of page 4
Enantiomers Two compounds that are non-superimposable mirror images (the two "hands") are called enantiomers . CH 3 Et Me H Pr Et Me H Pr mirror 3-methylhexane Et Me H Pr Et Me H Pr Me H H Me enantiomers
Background image of page 5

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

View Full DocumentRight Arrow Icon
Introduction To Stereochemistry Structural (constitutional) Isomers - Compounds of the same molecular formula with different connectivity (structure, constitution) Conformational Isomer s - Compounds of the same structure that differ in rotation around one or more single bonds Configurational Isomers or Stereoisomers - Compounds of the same structure that differ in one or more aspects of stereochemistry (how groups are oriented in space - enantiomers or diastereomers) 2-methylpentane 3-methylpentane Me H H H H Me Me H H Me H H Me H H Me 3-methylhexane 3-methylhexane We need a a way to describe the stereochemistry!
Background image of page 6
The CIP System Revisited Me H H Me 1 2 3 4 1 2 3 4 1. Rank each substituent attached to the stereocenter according to the CIP priority system (1 = highest, 4 = lowest) 2. "View" the compound with the lowest priority substituent pointing away from you Et Pr Me H 1 2 3 4 Pr Et Me H 1 2 3 4 Me H 1 2 3 4 3. Draw a circular arrow from connecting substituents 1–3 from highest to lowest priority. If the arrow moves clockwise, the sterocenter is labeled ( R ) [this stands for rectus ]. If the arrow moves counterclockwise, then the
Background image of page 7

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

View Full DocumentRight Arrow Icon
Image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Page1 / 30

Chapter 4 - Chapter 4: Stereochemistry Introduction To...

This preview shows document pages 1 - 8. Sign up to view the full document.

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