A-LEVEL CHEMISTRY, ORGANIC CHEMISTRY II. Flashcards
OPTICAL ISOMERISM.
OPTICAL ISOMERISM IS A FORM OF STEREIOSOMERISM, THEY HAVE THE SAME STRUCTURAL FORMULA BUT DIFFERENT ARRANGMENT OF ATOMS IN SPACE.
OPTICAL ISOMERS ARE MIRROR IMAGES OF EACH OTHER AND HAVE A CHIRAL CARBON CHAIN.
CHIRAL MOLECULE.
A CHIRAL MOLECULE HAS FOUR,4, DIFFERENT GROUPS ATTACHED TO A CARBON ATOM.
WE CAN ARRANGE THESE GROUPS IN TWO,2, DIFFERENT WAYS WHICH FORM TWO,2, DIFFERENT MOLECULES.
WE CALL THESE ENANTIOMERS.
ENANTIOMERS.
ENANTIOMERS ARE MIRRO IMAGES OF EACH OTHER AND ARE NON-SUPERIMPOSABLE.
NO MATTER WHICH WAY YOU TURN THEM THEY WILL NOT OVERLAP.
ENANTIOMERS, SHOWOING THEM.
FIRST WE NEED TO FIND THE CHIRAL CENTRE THEN DRAW THEM IN A TETRAHEDRAL 3D SHAPE TO SHOW THEM AS ENANTIOMERS.
OPTICALLY ACTIVE ISOMERS.
OPTICALLY ACTIVE ISOMERS WILL ROTATE PLANE POLARISED LIGHT.
THIS IS A METHOD OF DETECTING AN OPTICALLY ACTIVE COMPOUND.
STANDARD LIGHT OSCILLATES IN ALL DIRECTIONS.
WE PASS THE LIGHT THROUGH A POLAROID FILTER TO PRODUCE PLAIN POLARISED LIGHT.
THIS LIGHT ONLY OSCILLATES IN ONE,1, DIRECTION.
OPTICALLY ACTIVE COMPOUNDS WILL ROTATE PLANE POLARISED LIGHT.
ONE ENANTIOMER ROTATES LIGHT CLOCKWISE, THE OTHER WILL ROTATE IT ANTICLOCKWISE.
THEY WILL BOTH ROTATE TO THE SAME DEGREE, SUCH AS THEY WILL BOTH ROATE FIVE,5, DEGREES.
RACEMATES.
WHEN WE HAVE AN EQUAL AMOUNT OF EACH ENANTIOMER WE HAVE A RACEMIC MIXTURE.
RACEMATES, PLANE POLARISED LIGHT.
RACEMATES DO NOT ROTATE PLANE POLARISED LIGHT.
THE TWO,2, ENANTIOMERS ROTATE LIGHT IN OPPOSITE DIRECTIONS AND THEY CANCEL EACH OTHER OUT.
RACEMIC MIXTURE.
A RAECEMIC MIXTURE OF A CHRIAL PRODUCT IS OFTEN MADE BY REACTING ACHRIAL SUBSTANCES TOGETHER.
ACHIRAL.
A CARBON WITH TWO,2, GROUPS THAT ARE DIFFERENT.
ACHIRAL FORMING CHIRAL.
WHEN THE MOLECULES REACT THERE IS AN EVEN CHANCES OF FORMING AN ENANTIOMER.
YOU WILL FOR A CHIRAL.
AS WE SEE EITHER OF THE TWO,2, HYDROGEN ATOMS CAN BE REPLACED PRODUCING A MIXTURE OF TWO,2, ENANTIOMERS.
THRE IS A 50/50 CHANCE OF EITHER HYDROGEN BEING REPLACED SO THE ISOMERS ARE MADE IN EQUAL QUANTITIES.
PRODUCING ONE,1, ENANTIOMER FROM ACHIRAL.
IT IS VERY DIFFICULT TO ADAPT A REACTION TO ONLY PRODUCE ONE,1, ENANTIOMER AND IT CAN BE EXPENSIVE.
MOLECULES WITH PLANAR PROFILES RELATIONSHIP WITH RACEMIC PRODUCTS.
MOLECULES WITH PLANAR PROFILES CAN MAKE RACEMIC PRODUCTS.
FOR EXAMPLE IN SN1 MECHANISMS.
THESE REACTIOSN OCCUR WHEN WE HAVE AN ATTACK ON THE CARBOCATION OF A COMPOUND WHERE A GROUP BREAKS.
IN SN1 REACTIONS THE HALOGEN BREAKS OFF AND A CARBOCATION INTERMEDIATE IS FORMED.
THE REACTION BETWEEN Y- IONAND THE INTERMEDIATE INVOLVES ATTACKING THE PLANAR MOLECULE, PARTICULARLY THE C.
AS THIS IS PLANAR THE Y- ION CAN ATTACK FROM EITH ABOVE OR BELOW FORMING TWO,2, DIFFERENY ENANTIOMER.
PLANAR.
SOMETHING THAT IS FLAT.
TYPE OF ENANTIOMER FORMED.
THE TYPE OF THE ENANTIOMER FORMED WILL DEPEND ON IF THE Y- IONS ATTACKS FROM THE TOP OR BOTTOM OF THE PLANAR MOLECULE.
DUE TO THE PLANAR NATURE OF THE CARBOCATION THERE IS AN EVEN CHANCE OF THE NUCLEOPHILE ATTACKING FROM THE TOP AND THE BOTTOM.
THIS MEANS THAT WE ARE LIKELY TO GET A 50/50 MIXTURE OF BOTH ENANTIOMERS AND HENCE WE PRODUCE A RACEMIC MIXTURE OF PRODUCTS.
AS WITH ALL RACEMIX MIXTURES, THEY DO NOT ROTATE PLANE POLARISED LIGHT.
THE ROTATION OF PLANE POLARISED LIGHT BY EITHER ENANTIOMER CANCEL OUT.
OPTICAL ACTIVITY SN2 REACTIONS.
WITH AN SN2 REACTION WE HAVE A SINGLE ENATIOER PRODUCING ONE ENANTIOMER UNLIKE THE TWO,2, PRODUCED UNDER SN1 MECHANISMS.
IN AN SN2 REACTION BOTH Y- IONS AND THE HALOGENAOLKANE ARE REACTING IN ONE STEP AND THE NUCLEOPHILE A;WAYS ATTACK THE OPPOSITE SIDE OF THE LEAVING GROUP.
THIS MEANS WE ONLY PRODUCE ONE,1, PRODUCT AND THIS PRODUCT WILL ROTATE PLANE POLARISE DLIHT DIFFERENTLY TO THE REACTANT.
ALDEHYDES AND KETONES, FUNCTIONAL GROUP.
ALDEHYDES AND KETONES HAVE THE CARBONYL FUNCTIONAL GROUP, C=O.
ALDEHYDE AND KETONE DIFFERENCE.
THE DIFFERENCE BETWEEN AN ALDEHYDE AND A KETONE IS THE POSITION OF THE CARBONYL, C=O, GROUP,
ALDEYDES,
THEY HAVE THE CARBONYL, C=O, GROUP ON AN END CARBON.
KETONES,
THEY HAVE THE CARBONYL, C=O, GROUP ON AN INNER CARBON.
NAMING ALDEHYDES.
ALL ALDEYHYDES HAVE THE ENDING -al.
PROPANAL, ETHANAL.
NAMING KETONES.
ALL KETONES HAVE THE ENDING -one.
PROPANONE, PETAN-2-ONE.
ALDEHYDES AND KETONES BOILING POINTS.
ALDEHYDES AND KETONES HAVE RELATIVELY LOW BOILING POIRNTS IN COMPARISION TO ALCOHOLS, THIS IS ALL DOWN TO INTERMOLECULAR FORCES.
ALDEHYDES AND KETONES INTERACT WITH EACH OTHER VIA LONDON FORCES AND PERMANENT DIPOLE-PERMANENT DIPOLE BONDS AS THERE IS POLARITY WITHIN THE MOLECULES.
HOWEVER UNLIKE ALCOHOLS THEY DO NO HAVE AN O-H GROUP SO DO NOT HAVE INTERACT VIA THE STRONGEST INTERMOLECULAR FORCE, HYDROGEN BONDING.
THIS MEANS ALDEHYDED AND KETONES GENERALLY HAVE LOWER BOILING POINTS THAN THEIR ALCOHOL COUNTERPARTS.
ALDEHYDES AND KETONES, HYDROGEN BONDS.
ALDEHYDES AND KETONES CAN HYDROGEN BOND WITH WATER AND SO SOME HAVE TJHE ABILITY TO DISSOLVE IN WATER.
THE LONE PAIR OF ELECTRONS ON THE OXYGEN ON THE C=O CAN FORM HYDROGEN BONDS WITH THE DELTA POSITIVE HYDROGEN ATOMS ON WATER MOLECULES.