Intro to OC
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Why is sp bond stronger than sp2 and sp3
sp orbitals have the highest % of s character, which forms the shortest and strongest bond, effective orb overlap is the highest, thus strength of bond is highest
define isomerism, types of isomerism
same molecular structure, different structural formula(chain, positional, fn grp, cis-trans,enantiomerism)
criteria for cis trans
1) C-C bond must have restriction rotation of bond 2) 2 diff grps/atoms bonded to each C atom 3) rings: must have 8 or more carbon atoms to avoid ring strain
compare BP of cis and trans isomers
cis has ↑ BP than trans -both molecules have SMS -↑energy is req to overcome the pdpd int b/w polar cis molecules than the weaker idid b/w non polar trans molecules
compare MP of cis and trans isomers
trans has ↑ MP than cis -both molecules have SMS -trans molecule has a higher symmetry, can pack ↑ closely in its lattice structure than cis -↑energy is req to overcome the ↑extensive idid int in trans molecule
calc max no. of stereoisomers(CT+enan)
2^(m+n), m= no. of C=C that fulfils CT n= no. of chiral centres
define enantiomerism
stereoisomers that are mirror images of eo and are non superimposable on eo
criteria for enantiomerism
1) has a non superimposable mirror image(do not give the same structure when placed on top of eo) 2) has no internal plane of symmetry 3) has a chiral centre
why is racemic mixture optically inactive
-equal proportions of + and - enantiomers -both enantiomers rotate PPL in opposite directions by the same extent -no net rotation of PPL -optically inactive
what is meso compound
has more than 1 chiral centre and an internal plane of symmetry
total number of stereoisomers for meso compound
2^m -1
why is meso compound optically inactive
-internal plane of symmetry present -each chiral carbon will rotate PPL by the same angle in different directions -no net rotation of PPL - optically inactive
Describe the bonding in C=C bond(sp2)
The σ bond is formed by the head-on overlap of the sp2 hybrid orbitals on each C atom The π bond is formed by side-on overlap of the unhybridised p-orbital on each C atom
Explain why compounds with -OH groups in close proximity w/ one another have lower BP
-proximity of -OH groups allow for the formation of intramolecular hydrogen bonds -thus compound has less extensive intermolecular hydrogen bonding -hence BP is lower since less energy is required to overcome the less extensive intermolecular hydrogen bonding
Explain how cis trans isomerism arises
There is restricted rotation at C=C bond and each C of the C=C bond is bonded to 2 different groups. Hence there are 2 different compounds
Why do stereoisomers of a drug have different pharmacological activities
-Have diff arrangement of atoms in 3D space → have diff binding properties to chiral binding sites in the body such as enzymes and receptors
Define stereoisomers
Molecules that have same structural formula but different spatial arrangements
Compare stability of trans-alkene vs cis-alkene
It has 2 bulky groups far from each other, making it ↑ stable due to ↓steric hindrance
Compare MP of meso compound vs typical enantiomers
Meso compound has ↓MP as its molecules are ↓closely packed compared to enantiomers where only 1 enantiomer is present