Chemistry- Unit 4- Nomenclature and isomerism in organic chemistry

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Name of the system for naming?
IUPAC
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What is a root?
root tells us the longest unbranched hydrocarbon chain or ring.
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what does the syllable after the root tell us?
If theres any double bonds eg: ane = none, ene= 2 and yne = triple bond.
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What do prefixs and suffixs indicate?
Changes made to the root molecule eg: addition of groups. Example of a prefix: methly (ch3) and suffix ethanol (alcohol).
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haloalkanes? carboxylic acids? anhydrides?
halo-ane (eg: chloromethane) , RCOOH (ethanoic acid) , RCOOCOR (ethanoic anhydride)
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esters? amides? nitriles? aldehydes? ketones?
RCOOR (propyl ethanoate) , RCONH2 (ethanamide) , RCT triple N ethanenitril , RCHO ethanal, RCOR propanone
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amines?
RNH2 (ethylamine)
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What are structural isomers? Examples?
Same molecular formula but a different structural formula. Posistional, functional, chain.
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What are steroisomers?
compounds with same structural formula but differ in the arrangement of the bonds in space.
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Examples? What is E-Z?
E-Z and optical isomerism. E-Z tells us about posistions of substituents at either side of a C-C double bond. If they are on the same side its Z while if on opposite sides its E.
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Why can these occur?
as theres no rotation around a double bond so they have fixed positions.
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What is optical isomerism?
can only occur when four diffrent substituents are attached to one carbon atom. This causes two isomers which are mirror images of each other but not identical. Is because of diffrent ways you can arrange 4 different groups around a C atom.
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Why are they not identical?
Because even when they are rotated to each substituent being in the same posistion, they are not the same, as they cannot be superimposed onto the other.
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Example with shoes?
left shoe and right shoe. They are mirror images but are not identical.
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What is diffrent between the two isomers?
they differ in the ways they rotate the plane of polarisaion of polarised light ; either clockwise (+ isomer or D ) or anticlockwise (-isomer or L) .
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what does a polaroid filter do?
Light consits of vibrating electrical and magnetic fields, occurring in all directions at right angles. The filter cuts all vibrations except for those in that plane, so they vibrate only in one direction.
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How can we measure optical rotation using a polarimeter?
Pass polarised light through 2 solutions of the same conc, each with a diffrent optical isomer of same substance. One will cause the plane of light to rotate clockwise (+ isomer) while the other anti-clockwise (- isomer)
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what does chiral mean? What are the two isomers called? The carbon bonded to the 4 diffrent groups is called? what always has a chiral center?
means handed. Pair of enantiomers. The chiral center (asymmetric carbon atom or *) . all alpha amino acids.
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What is a racemate?
A racemate is a 50:50 mixture of thw two optica
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negativly charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCN
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
56 of 127
How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
58 of 127
what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
59 of 127
Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed?
the chiral center has not been affected by the
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed? Is this usual?
the chiral center has not been affected by the hydrolysis reaction therefore we still have a racemate mixture. Within industry this is common but in nature it usually only exists as one of the optical isomers.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed? Is this usual?
the chiral center has not been affected by the hydrolysis reaction therefore we still have a racemate mixture. Within industry this is common but in nature it usually only exists as one of the optical isomers.
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the two optical isomers?
Diagrams- one with NC from the top, other from bottom (stage 1) and drawing, H
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
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what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed? Is this usual?
the chiral center has not been affected by the hydrolysis reaction therefore we still have a racemate mixture. Within industry this is common but in nature it usually only exists as one of the optical isomers.
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the two optical isomers?
Diagrams- one with NC from the top, other from bottom (stage 1).
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
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Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
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Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
96 of 127
what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
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Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
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Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed? Is this usual?
the chiral center has not been affected by the hydrolysis reaction therefore we still have a racemate mixture. Within industry this is common but in nature it usually only exists as one of the optical isomers.
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the two optical isomers?
Diagrams- one with NC from the top, other from bottom (stage 1).
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How can we get only one isomer in industry?
Use a receptor, molecule of active ingredient fitting an area of a cell thus because its 3 dimentisonal only one of a pai will fit.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
104 of 127
Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
105 of 127
How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
106 of 127
Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
107 of 127
what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
108 of 127
Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
109 of 127
Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed? Is this usual?
the chiral center has not been affected by the hydrolysis reaction therefore we still have a racemate mixture. Within industry this is common but in nature it usually only exists as one of the optical isomers.
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the two optical isomers?
Diagrams- one with NC from the top, other from bottom (stage 1).
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How can we get only one isomer in industry?
Use a receptor, molecule of active ingredient fitting an area of a cell thus because its 3 dimentisonal only one of a pai will fit.
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what is usual in drugs? How to fix?
One optical isomer will be effective while the other is simply imactive. We can either seperate them (expensie), sell the mixture (wasteful and expensive) or alternative to making just one of them.
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What is a racemate? What is it described as and why?
A racemate is a 50:50 mixture of thw two optical isomers. Described as not optically active because the two isomers, as they cause polarised light to rotate in opposite directions, cancel each other out.
116 of 127
Structure of 2-hydroxypropanoic acid?
C(chiral carbon) with a OH, CH3, COH2.
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How many stages in the synthesis? what is it made from? What reaction is it?
2 stages and ethanol and nucleophillic addition
118 of 127
Stage 1?
arrow from the electrons on the CN- to the negatively charged chiral carbon. Another arrow from the double bond between C and O to the oxygen atom.
119 of 127
what do we form? What is this usually?
2-hydroxypropanenitrile and its usually a racemate mixture because it has a chiral carbon which the reaction does not favor regarding which enantomer forms.
120 of 127
Stage 2?
Nitrile group gets converted to carboxylic group by reacting with water acidified with dilute HCL in a hydrolysis reaction.
121 of 127
Diagram?
3 lone pairs on the O atom, arrow from one of these to a H+.
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equations for stage 1 and 2?
CH3COH + HCN ---> CH3CHCNOH and CH3CHCNOH + HCL + 2H20 ---> CH£CHCOOHCH3
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what has however not changed? Is this usual?
the chiral center has not been affected by the hydrolysis reaction therefore we still have a racemate mixture. Within industry this is common but in nature it usually only exists as one of the optical isomers.
124 of 127
the two optical isomers?
Diagrams- one with NC from the top, other from bottom (stage 1).
125 of 127
How can we get only one isomer in industry?
Use a receptor, molecule of active ingredient fitting an area of a cell thus because its 3 dimentisonal only one of a pai will fit.
126 of 127
what is usual in drugs? How to fix?
One optical isomer will be effective while the other is simply imactive. We can either seperate them (expensie), sell the mixture (wasteful and expensive) or alternative to making just one of them.
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Card 2

Front

What is a root?

Back

root tells us the longest unbranched hydrocarbon chain or ring.

Card 3

Front

what does the syllable after the root tell us?

Back

Preview of the front of card 3

Card 4

Front

What do prefixs and suffixs indicate?

Back

Preview of the front of card 4

Card 5

Front

haloalkanes? carboxylic acids? anhydrides?

Back

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