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IC / Chemistry / CHEM 22100 / How would you define an enantiomers?

How would you define an enantiomers?

How would you define an enantiomers?

Description

School: Ithaca College
Department: Chemistry
Course: Organic Chemistry 1
Professor: Steven russo
Term: Spring 2016
Tags: Organic Chemistry Notes Stereochemistry
Cost: 25
Name: Organic chemistry Week 3
Description: Notes for week 3
Uploaded: 02/14/2016
6 Pages 211 Views 0 Unlocks
Reviews


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"}ol.lst-kix_oxrb6e94ggth-6.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-6 0}.lst-kix_aa3han1mim08-4 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-4,lower-latin) ". "}.lst-kix_rw5fh2ni62l1-3 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-3}.lst-kix_aa3han1mim08-2 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-2,lower-roman) ". "}.lst-kix_aa3han1mim08-3 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-3,decimal) ". "}.lst-kix_aa3han1mim08-1 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-1,lower-latin) ". "}ol.lst-kix_oxrb6e94ggth-0.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-0 0}ol.lst-kix_rw5fh2ni62l1-5.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-5 0}.lst-kix_aa3han1mim08-0 > li{counter-increment:lst-ctn-kix_aa3han1mim08-0}.lst-kix_aa3han1mim08-0 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-0,decimal) ". "}.lst-kix_oxrb6e94ggth-5 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-5}ol.lst-kix_oxrb6e94ggth-7.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-7 0}.lst-kix_u9vdz4df1v91-4 > li:before{content:"- "}.lst-kix_u9vdz4df1v91-3 > li:before{content:"- "}.lst-kix_u312u9mo6d7n-6 > li:before{content:"- "}.lst-kix_oxrb6e94ggth-2 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-2}.lst-kix_u9vdz4df1v91-2 > li:before{content:"- "}ol.lst-kix_aa3han1mim08-1.start{counter-reset:lst-ctn-kix_aa3han1mim08-1 0}.lst-kix_u312u9mo6d7n-7 > li:before{content:"- "}.lst-kix_u9vdz4df1v91-0 > li:before{content:"- "}.lst-kix_aa3han1mim08-6 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-6,decimal) ". "}.lst-kix_u9vdz4df1v91-1 > li:before{content:"- "}.lst-kix_aa3han1mim08-7 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-7,lower-latin) ". "}.lst-kix_u312u9mo6d7n-8 > li:before{content:"- "}.lst-kix_aa3han1mim08-8 > li:before{content:"" counter(lst-ctn-kix_aa3han1mim08-8,lower-roman) ". "}.lst-kix_oxrb6e94ggth-4 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-4}ol.lst-kix_oxrb6e94ggth-8.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-8 0}.lst-kix_u312u9mo6d7n-5 > li:before{content:"- "}.lst-kix_u9vdz4df1v91-5 > li:before{content:"- "}.lst-kix_u312u9mo6d7n-3 > li:before{content:"- "}.lst-kix_u312u9mo6d7n-1 > li:before{content:"- "}.lst-kix_u9vdz4df1v91-7 > li:before{content:"- "}ol.lst-kix_rw5fh2ni62l1-2.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-2 0}.lst-kix_aa3han1mim08-2 > li{counter-increment:lst-ctn-kix_aa3han1mim08-2}.lst-kix_rw5fh2ni62l1-5 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-5}.lst-kix_oxrb6e94ggth-3 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-3}ul.lst-kix_dx7fxv8t1cyq-7{list-style-type:none}.lst-kix_kit7ea8zzmax-8 > li:before{content:"- "}ul.lst-kix_dx7fxv8t1cyq-6{list-style-type:none}ul.lst-kix_dx7fxv8t1cyq-8{list-style-type:none}ul.lst-kix_dx7fxv8t1cyq-3{list-style-type:none}.lst-kix_kit7ea8zzmax-6 > li:before{content:"- "}ul.lst-kix_dx7fxv8t1cyq-2{list-style-type:none}ul.lst-kix_dx7fxv8t1cyq-5{list-style-type:none}ul.lst-kix_dx7fxv8t1cyq-4{list-style-type:none}.lst-kix_aa3han1mim08-1 > li{counter-increment:lst-ctn-kix_aa3han1mim08-1}.lst-kix_kit7ea8zzmax-4 > li:before{content:"- "}ul.lst-kix_dx7fxv8t1cyq-1{list-style-type:none}ul.lst-kix_dx7fxv8t1cyq-0{list-style-type:none}.lst-kix_aa3han1mim08-7 > li{counter-increment:lst-ctn-kix_aa3han1mim08-7}.lst-kix_kit7ea8zzmax-0 > li:before{content:"- "}.lst-kix_rw5fh2ni62l1-4 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-4}.lst-kix_kit7ea8zzmax-2 > li:before{content:"- "}.lst-kix_oxrb6e94ggth-2 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-2,lower-roman) ". "}.lst-kix_oxrb6e94ggth-0 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-0,decimal) ". "}.lst-kix_oxrb6e94ggth-4 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-4,lower-latin) ". "}ol.lst-kix_aa3han1mim08-6{list-style-type:none}ol.lst-kix_aa3han1mim08-5{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-1.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-1 0}ol.lst-kix_aa3han1mim08-8{list-style-type:none}ol.lst-kix_aa3han1mim08-7{list-style-type:none}.lst-kix_oxrb6e94ggth-8 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-8,lower-roman) ". "}.lst-kix_oxrb6e94ggth-6 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-6,decimal) ". "}ol.lst-kix_aa3han1mim08-0{list-style-type:none}ol.lst-kix_aa3han1mim08-2{list-style-type:none}ol.lst-kix_aa3han1mim08-1{list-style-type:none}ol.lst-kix_aa3han1mim08-4{list-style-type:none}ol.lst-kix_aa3han1mim08-3{list-style-type:none}.lst-kix_rw5fh2ni62l1-0 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-0}ul.lst-kix_u312u9mo6d7n-5{list-style-type:none}ul.lst-kix_u312u9mo6d7n-6{list-style-type:none}ul.lst-kix_u312u9mo6d7n-3{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-3.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-3 0}ul.lst-kix_u312u9mo6d7n-4{list-style-type:none}ul.lst-kix_u312u9mo6d7n-1{list-style-type:none}ul.lst-kix_u312u9mo6d7n-2{list-style-type:none}ul.lst-kix_u312u9mo6d7n-0{list-style-type:none}.lst-kix_66jhpt25xna6-0 > li:before{content:"- "}.lst-kix_66jhpt25xna6-1 > li:before{content:"- "}.lst-kix_66jhpt25xna6-2 > li:before{content:"- "}.lst-kix_rw5fh2ni62l1-8 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-8,lower-roman) ". "}ul.lst-kix_u312u9mo6d7n-7{list-style-type:none}ul.lst-kix_u312u9mo6d7n-8{list-style-type:none}.lst-kix_66jhpt25xna6-4 > li:before{content:"- "}.lst-kix_66jhpt25xna6-3 > li:before{content:"- "}.lst-kix_66jhpt25xna6-5 > li:before{content:"- "}ol.lst-kix_aa3han1mim08-3.start{counter-reset:lst-ctn-kix_aa3han1mim08-3 0}ul.lst-kix_66jhpt25xna6-0{list-style-type:none}ul.lst-kix_66jhpt25xna6-5{list-style-type:none}ul.lst-kix_66jhpt25xna6-6{list-style-type:none}.lst-kix_rw5fh2ni62l1-2 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-2}ul.lst-kix_66jhpt25xna6-7{list-style-type:none}ul.lst-kix_66jhpt25xna6-8{list-style-type:none}ul.lst-kix_66jhpt25xna6-1{list-style-type:none}ul.lst-kix_66jhpt25xna6-2{list-style-type:none}.lst-kix_aa3han1mim08-8 > li{counter-increment:lst-ctn-kix_aa3han1mim08-8}ul.lst-kix_66jhpt25xna6-3{list-style-type:none}ul.lst-kix_66jhpt25xna6-4{list-style-type:none}ol.lst-kix_aa3han1mim08-2.start{counter-reset:lst-ctn-kix_aa3han1mim08-2 0}ol.lst-kix_rw5fh2ni62l1-7{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-8{list-style-type:none}.lst-kix_dx7fxv8t1cyq-8 > li:before{content:"- "}ol.lst-kix_rw5fh2ni62l1-3{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-4{list-style-type:none}.lst-kix_oxrb6e94ggth-8 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-8}.lst-kix_dx7fxv8t1cyq-7 > li:before{content:"- "}ol.lst-kix_rw5fh2ni62l1-5{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-6{list-style-type:none}.lst-kix_dx7fxv8t1cyq-6 > li:before{content:"- "}ol.lst-kix_rw5fh2ni62l1-0{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-1{list-style-type:none}ol.lst-kix_rw5fh2ni62l1-2{list-style-type:none}.lst-kix_dx7fxv8t1cyq-5 > li:before{content:"- "}ul.lst-kix_u9vdz4df1v91-6{list-style-type:none}.lst-kix_dx7fxv8t1cyq-2 > li:before{content:"- "}.lst-kix_rw5fh2ni62l1-1 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-1,lower-latin) ". "}.lst-kix_66jhpt25xna6-8 > li:before{content:"- "}ul.lst-kix_u9vdz4df1v91-7{list-style-type:none}ul.lst-kix_u9vdz4df1v91-8{list-style-type:none}.lst-kix_66jhpt25xna6-7 > li:before{content:"- "}ol.lst-kix_rw5fh2ni62l1-4.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-4 0}.lst-kix_dx7fxv8t1cyq-0 > li:before{content:"- "}.lst-kix_dx7fxv8t1cyq-4 > li:before{content:"- "}.lst-kix_66jhpt25xna6-6 > li:before{content:"- "}.lst-kix_dx7fxv8t1cyq-3 > li:before{content:"- "}.lst-kix_aa3han1mim08-6 > li{counter-increment:lst-ctn-kix_aa3han1mim08-6}.lst-kix_rw5fh2ni62l1-0 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-0,decimal) ". "}.lst-kix_rw5fh2ni62l1-4 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-4,lower-latin) ". "}ol.lst-kix_aa3han1mim08-8.start{counter-reset:lst-ctn-kix_aa3han1mim08-8 0}.lst-kix_rw5fh2ni62l1-5 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-5,lower-roman) ". "}.lst-kix_rw5fh2ni62l1-7 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-7,lower-latin) ". "}.lst-kix_dx7fxv8t1cyq-1 > li:before{content:"- "}.lst-kix_rw5fh2ni62l1-6 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-6,decimal) ". "}ul.lst-kix_u9vdz4df1v91-0{list-style-type:none}ul.lst-kix_u9vdz4df1v91-1{list-style-type:none}ul.lst-kix_u9vdz4df1v91-2{list-style-type:none}.lst-kix_rw5fh2ni62l1-3 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-3,decimal) ". "}ul.lst-kix_u9vdz4df1v91-3{list-style-type:none}ul.lst-kix_u9vdz4df1v91-4{list-style-type:none}.lst-kix_rw5fh2ni62l1-2 > li:before{content:"" counter(lst-ctn-kix_rw5fh2ni62l1-2,lower-roman) ". "}ul.lst-kix_u9vdz4df1v91-5{list-style-type:none}ul.lst-kix_kit7ea8zzmax-8{list-style-type:none}.lst-kix_rw5fh2ni62l1-6 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-6}ol.lst-kix_aa3han1mim08-4.start{counter-reset:lst-ctn-kix_aa3han1mim08-4 0}.lst-kix_aa3han1mim08-4 > li{counter-increment:lst-ctn-kix_aa3han1mim08-4}ol.lst-kix_aa3han1mim08-7.start{counter-reset:lst-ctn-kix_aa3han1mim08-7 0}.lst-kix_u312u9mo6d7n-4 > li:before{content:"- "}ol.lst-kix_oxrb6e94ggth-5.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-5 0}.lst-kix_u9vdz4df1v91-6 > li:before{content:"- "}.lst-kix_u9vdz4df1v91-8 > li:before{content:"- "}ul.lst-kix_kit7ea8zzmax-1{list-style-type:none}ul.lst-kix_kit7ea8zzmax-0{list-style-type:none}.lst-kix_u312u9mo6d7n-0 > li:before{content:"- "}.lst-kix_u312u9mo6d7n-2 > li:before{content:"- "}ul.lst-kix_kit7ea8zzmax-3{list-style-type:none}ul.lst-kix_kit7ea8zzmax-2{list-style-type:none}.lst-kix_aa3han1mim08-3 > li{counter-increment:lst-ctn-kix_aa3han1mim08-3}ul.lst-kix_kit7ea8zzmax-5{list-style-type:none}ul.lst-kix_kit7ea8zzmax-4{list-style-type:none}ul.lst-kix_kit7ea8zzmax-7{list-style-type:none}.lst-kix_rw5fh2ni62l1-7 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-7}ul.lst-kix_kit7ea8zzmax-6{list-style-type:none}.lst-kix_rw5fh2ni62l1-8 > li{counter-increment:lst-ctn-kix_rw5fh2ni62l1-8}ol.lst-kix_oxrb6e94ggth-2.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-2 0}.lst-kix_aa3han1mim08-5 > li{counter-increment:lst-ctn-kix_aa3han1mim08-5}.lst-kix_oxrb6e94ggth-6 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-6}.lst-kix_oxrb6e94ggth-7 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-7}.lst-kix_kit7ea8zzmax-5 > li:before{content:"- "}ol.lst-kix_oxrb6e94ggth-3.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-3 0}.lst-kix_kit7ea8zzmax-3 > li:before{content:"- "}.lst-kix_kit7ea8zzmax-1 > li:before{content:"- "}ol.lst-kix_rw5fh2ni62l1-8.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-8 0}ol.lst-kix_aa3han1mim08-5.start{counter-reset:lst-ctn-kix_aa3han1mim08-5 0}.lst-kix_oxrb6e94ggth-1 > li{counter-increment:lst-ctn-kix_oxrb6e94ggth-1}.lst-kix_oxrb6e94ggth-3 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-3,decimal) ". "}.lst-kix_oxrb6e94ggth-1 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-1,lower-latin) ". "}ol.lst-kix_rw5fh2ni62l1-7.start{counter-reset:lst-ctn-kix_rw5fh2ni62l1-7 0}.lst-kix_oxrb6e94ggth-7 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-7,lower-latin) ". "}ol.lst-kix_oxrb6e94ggth-4.start{counter-reset:lst-ctn-kix_oxrb6e94ggth-4 0}.lst-kix_kit7ea8zzmax-7 > li:before{content:"- "}.lst-kix_oxrb6e94ggth-5 > li:before{content:"" counter(lst-ctn-kix_oxrb6e94ggth-5,lower-roman) ". "}

Example:Don't forget about the age old question of What are the uses of bone markings?

If you want to learn more check out What leads to a child's development of secure attachment?

Transdecalin

CIS decalin

We also discuss several other topics like What is a load effective address?

Quiz ReviewDon't forget about the age old question of 132 psi to mmhg

ResonanceDon't forget about the age old question of Organization: a group of individuals who want to achieve the same objectives (?

Example:

Non bonding e- pairDon't forget about the age old question of What is Kruskal's Algorithm?

Adjacent to bond

Example:

Polar bond

Why would the structure “want” to be like this?

So it can react with other molecules at the carbon!!

Enantiomers

  • Stereoisomers that are superimposable mirror images
  • Same formula, same connectivity (same flat structure), but different in 3D

“Handedness” in Chemistry, Chiral - handed

Chiral molecules have an enantiomer

Achiral molecules don’t have enantiomers

Stereoisomers

  • Enantiomers
  • Some physical properties (except for optical rotation)
  • Diastereomers
  • Different physical properties

Example:

Stereoisomers, but NOT enantiomers

Molecules with < 1 stereogenic carbons…

        Number of stereoisomers = 2n

        Where n = number of stereogenic C’s

But remember, any molecule has one enantiomer

Some molecules are chiral without a stereogenic C

                                                                Rotations - not same as R

Chapter 5 - stereochemistry

Stereoisomers - same formula, same connectivity different in 3D

“Stereogenic” carbons

  • SP3 hybridized carbon with 4 different groups attached

Enantiomers: stereoisomers that are non superimposable mirror images

Diastereomers: stereoisomers that are not enantiomers

RPS designation of stereogenic carbons

  1. Assign “Priority” to each group according to atomic number (increase number = highest priority) of the main atom
  • If there a tie, go one molecule out,

Example: both have Cs, but number 2 has “0” after!!

  1. Rotate molecule to have lowest group in back (as dashed group) rip molecule!!

The SS and RR are enantiomers

How do we know? Draw mirror images

Mirror image of RR:

When mirror image, but is super imposable: not enantiomers

  1. Connect molecules with arrows 1 → 4. If arrows spin molecules,...

        Left = S isomer

        Right = R isomer

Example:

Name: S - 3 methyl hexane

**Remember priority is based on next individual atom out, NOT size of group or overall atomic weight of group**

Acknowledging that the double bonded carbons bonded TWICE

How to redraw!!                        R - isomer!!

  1. “Hold” the non - wedgeldash group that is NOT the 4th priority
  2. Rotate until 4th group is at the back

**As long as 4 is in back (dashed line), the direction is based on 1, 2, and 3s order

“R and S” designation only in alkanes over hexane

Chirality without stereogenic C

Compared, are they super imposable? No! Molecule is chiral both have enantiomers

Diastereomers: stereoisomers that are not enantiomers

  1. Compounds with > 1 stereogenic C, 2n stereoisomers where n = number of stereogenic C’s

Example:

22 = 4 stereoisomers

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