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Flashcards in Organic Chemistry Deck (39):
1

carbon-carbon sigma bonds

list all possibilities strong to weak (6)

identify hybridisation (ie how many p)

identify shortest bond length

draw examples

 

 

strongest has most s character and least p

(similar to why sigma bonds are stronger than pi bonds)

       137 Angstroms

sp-sp               2p

sp-sp2          3p

sp-sp3              4p

sp2-sp2           4p

sp2-sp3           5p

sp3-sp3            6p

154 Angstroms

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2

Structural formulae

List and describe possible structural formulae (7) 

1. Lewis dot structure

2. Dash formula - shows the bonds between atoms but not their 3D structure H-C-C..

3. Condensed formula - CH3CH2...

4. Bond line formula - intersections, corners and endings are assumed to be C unless other drawn in. H not drawn

5. Fischer projection - vertical lines into page, horizontal out of page

6. Newman projection - view straight down axis of one of the sigma bonds. Circle and intersecting lines are C

7. Dash-line-wedge model  - wedge out of page, dashed into

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3

Structures

Draw

n-propyl

isopropyl

n-butyl

isobutyl

sec-butyl

tert-butyl

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4

Straight carbon chain naming

The general formula for a alkane is ...

 

The general formula for an alkene is ...

 

The general formula for an alkyne is ...

The general formula for an alkane is Cn H2n+2

 

The general formula for an alkene is Cn H2n

 

The general formula for an alkene is Cn H2n-2

 

 

5

In organic chemistry, a saturated compound has ....

In organic chemistry, a saturated compound has no double or triple bonds

6

Saturated compounds

Describe saturated and unsaturated carbon compounds

Full complement of hydrogens = saturated.

In organic chemistry, a saturated compound is a chemical compound that has a chain of carbon atoms linked together by single bonds. Alkanes are an example of saturated compounds.

An unsaturated compound is a chemical compound that contains carbon-carbon double bonds or triple bonds, such as those found in alkenes or alkynes, respectively. Saturated and unsaturated compounds need not consist only of a carbon atom chain. They can form straight chain, branched chain, or ring arrangements. They can have functional groups, as well.

 

In other unsaturated hydrocarbons, the double bond between two carbons prevents rotation of the atoms about the bond, locking them into specific structural formations. When attached atoms occupy similar positions on each carbon, they are referred to as "cis", and when they are on opposite sides, they are called "trans". Most natural hydrocarbons exist in the cis state, but artificially manufactured hydrocarbons are trans. The body lacks the enzymes to properly break down the trans configuration. This is why trans fats are viewed as dangerous and unhealthy, as they tend to build up. Unsaturated compounds of the two formations are classified as geometric isomers of one another.

7

Electron pushing arrows

1. What are they and where are used?

2. What are the parts of the arrow and what do they mean?

3. Between two atoms what are the three possible combinations for an electron?

4. How can you move between these combinations?

1. They show electron movement from one atom to another.

2. Electron moves from tail to head(>)

3. Own eg a lone pair completely owned by an atom

Share eg a covalent bond

Lack eg a lone pair on a completely different atom

4. One step at a time

Own Share Lack

 

8

Functional groups - nomenclature

Give the prefix and suffix of the

1. Ether

 

1. Ether   - alkoxy - ane

2. Aldehyde  -formyl   -al (-carbaldehyde)

3. Ketone     -oxo   -one

4. Ester      (R)-oxycarbonyl  -oate

5. Anhydride     -oic **             -anhydride

6. Epoxide  -epoxy              -oxide

** eg propanoic anhydride (for symmetrical) or propanoic ehtanoic anhydride

9

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

1. Benzene ring

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Benzene ring  -phenyl  -benzene

2. Enol   -??          (E) ... -ol

3. Enoloate  

10

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine     -amino     -amine

2. Nitro    -nitro   -(always substituent)

3. Nitrile    -cyano    -nitrile

4. Imine     -??     -imine

5. Amide   -carbonyl      -carboxamide(amide)

6. Enamine   -??   -??

11

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

 

4. Acyl halide

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

3. Alkyl halide   -haloalkyl   -ane

 

4. Acyl halide          -n/a    -oyl halide

(2-methylpropanoyl chloride)

 

 

 

12

Electron pushing arrows

1. What is the most important thing in organic chemistry?

 

2. What are the valid charges in organic chemistry (at least in org 1 and 2)?

 

3. How do electron pushing arrows tell us to break a bond?

1. The charges

 

2.   -1  0  +1

 

3. The tail is on the bond

13

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

6. Epoxide

1. Ether   - alkoxy - ane

2. Aldehyde  -formyl   -al (-carbaldehyde)

3. Ketone     -oxo   -one

4. Ester      (R)-oxycarbonyl  -oate

5. Anhydride     -oic **             -anhydride

6. Epoxide  -epoxy              -oxide

** eg propanoic anhydride (for symmetrical) or propanoic ehtanoic anhydride

14

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

5. Anhydride

 

1. Ether   - alkoxy - ane

2. Aldehyde  -formyl   -al (-carbaldehyde)

3. Ketone     -oxo   -one

4. Ester      (R)-oxycarbonyl  -oate

5. Anhydride     -oic **             -anhydride

6. Epoxide  -epoxy              -oxide

** eg propanoic anhydride (for symmetrical) or propanoic ehtanoic anhydride

15

Functional groups - nomenclature

Give the prefix and suffix of the functional group

 

4. Ester

 

1. Ether   - alkoxy - ane

2. Aldehyde  -formyl   -al (-carbaldehyde)

3. Ketone     -oxo   -one

4. Ester      (R)-oxycarbonyl  -oate

5. Anhydride     -oic **             -anhydride

6. Epoxide  -epoxy              -oxide

** eg propanoic anhydride (for symmetrical) or propanoic ehtanoic anhydride

16

Functional groups - nomenclature

Give the prefix and suffix of  functional groups

 

3. Ketone

 

1. Ether   - alkoxy - ane

2. Aldehyde  -formyl   -al (-carbaldehyde)

3. Ketone     -oxo   -one

4. Ester      (R)-oxycarbonyl  -oate

5. Anhydride     -oic **             -anhydride

6. Epoxide  -epoxy              -oxide

** eg propanoic anhydride (for symmetrical) or propanoic ehtanoic anhydride

17

Functional groups - nomenclature

Give the prefix and suffix of

2. Aldehyde

 

1. Ether   - alkoxy - ane

2. Aldehyde  -formyl   -al (-carbaldehyde)

3. Ketone     -oxo   -one

4. Ester      (R)-oxycarbonyl  -oate

5. Anhydride     -oic **             -anhydride

6. Epoxide  -epoxy              -oxide

** eg propanoic anhydride (for symmetrical) or propanoic ehtanoic anhydride

18

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

1. Alcohol

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Alcohol    -hydroxy   -ol

2. Carboxylic acid  -carboxy    -carboxylic acid(-oic acid)

3. Alkane  -alkyl    -ane

4. Alkene   -alkenyl  -ene

5. Alkyne   -alkynyl   -yne

19

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

 

2. Carboxylic acid

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Alcohol    -hydroxy   -ol

2. Carboxylic acid  -carboxy    -carboxylic acid(-oic acid)

3. Alkane  -alkyl    -ane

4. Alkene   -alkenyl  -ene

5. Alkyne   -alkynyl   -yne

20

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

 

3. Alkane

4. Alkene

5. Alkyne

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Alcohol    -hydroxy   -ol

2. Carboxylic acid  -carboxy    -carboxylic acid(-oic acid)

3. Alkane  -alkyl    -ane

4. Alkene   -alkenyl  -ene

5. Alkyne   -alkynyl   -yne

21

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

6. Enamine (not yet)

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine     -amino     -amine

2. Nitro    -nitro   -(always substituent)

3. Nitrile    -cyano    -nitrile

4. Imine     -??     -imine

5. Amide   -carbonyl      -carboxamide(amide)

6. Enamine   -??   -??

22

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

5. Amide

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine     -amino     -amine

2. Nitro    -nitro   -(always substituent)

3. Nitrile    -cyano    -nitrile

4. Imine     -??     -imine

5. Amide   -carbonyl      -carboxamide(amide)

6. Enamine   -??   -??

23

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

2. Nitro

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine     -amino     -amine

2. Nitro    -nitro   -(always substituent)

3. Nitrile    -cyano    -nitrile

4. Imine     -??     -imine

5. Amide   -carbonyl      -carboxamide(amide)

6. Enamine   -??   -??

24

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

3. Nitrile

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine     -amino     -amine

2. Nitro    -nitro   -(always substituent)

3. Nitrile    -cyano    -nitrile

4. Imine     -??     -imine

5. Amide   -carbonyl      -carboxamide(amide)

6. Enamine   -??   -??

25

Functional groups - nomenclature

Give the prefix and suffix of the following functional group

 

2. Enol  (just suffix)

3. Enoloate  (not yet)

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Benzene ring  -phenyl  -benzene

2. Enol   -??          (E) ... -ol

3. Enoloate  

26

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

4. Imine  (suffix only)

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Amine     -amino     -amine

2. Nitro    -nitro   -(always substituent)

3. Nitrile    -cyano    -nitrile

4. Imine     -??     -imine

5. Amide   -carbonyl      -carboxamide(amide)

6. Enamine   -??   -??

27

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

1. Sulfide

 

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

 

 

1. Sulfide  -n/a         -sulfide (eg 2-butyl methyl sulfide )

 

28

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

2. Thiol

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

2. Thiol  -mercapto   -thiol

29

Organic chemistry

What is a carbonyl group?

A carbonyl group is a chemically organic functional group composed of a carbon atom double-bonded to an oxygen atom --> [C=O]

The simplest carbonyl groups are aldehydes and ketones usually attached to another carbon compound.

These structures can be found in many aromatic compounds contributing to smell and taste.

30

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

 

3. Alkyl halide

Functional groups - nomenclature

Give the prefix and suffix of the following functional groups

3. Alkyl halide             -haloalkyl   -ane

 

4. Acyl halide   -n/a    -oyl halide 

(2-methylpropanoyl chloride)

31

Two functional groups containing sulfur

Sulfide     R-S-R

 

Thiol   R-SH

32

Two functional groups containing Halogens

 

 

Alkyl Halide  R-X   

 

 

 

Acyl halide   sim ketone

33

Six functional groups containing Nitrogen

Amine

Nitro

Nitrile

Imine

Amide

Enamine

google doc for functional groups

34

Carbon double bonds

1. A C=C bond is a ..?...?...?..  in a molecule.

It should be the site of a lot of .?...?..

1. A C=C bond is a reaction hot spot in a molecule. 

It should be the site of a lot of chemical action

35

nucleophilic substitution

A nucleophile is an ..?.. rich species that will react with an electron ..?.. species
A substitution implies that one group ..?.. another.

 

What does the term "nucleophilic substitution" imply ?

A nucleophile is an electron rich species that will react with an electron poor species
A substitution implies that one group replaces another.

Nucleophilic substitution reactions occur when an electron rich species, the nucleophile, reacts at an electrophilic saturated C atom attached to an electronegative group (important), the leaving group


The electrophilic C can be recognised by looking for the polar σ bond due to the presence of an electronegative substituent (esp. C-Cl, C-Br, C-I and C-O)

Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups.

Of particular importance are the reactions of alkyl halides (R-X) and alcohols (R-OH)

For alcohols, the range of substitution reactions possible can be increased by utilising the tosylates (R-OTs), an alternative method of converting the -OH to a better leaving group.

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36

nucleophilic substitution

 

1. What are the three conditions for Nucleophilic substitution reactions to occur?

 

What does the term "nucleophilic substitution" imply ?

A nucleophile is an electron rich species that will react with an electron poor species
A substitution implies that one group replaces another.

Nucleophilic substitution reactions occur when an

electron rich species, the nucleophile,

reacts at an electrophilic saturated C atom attached to

an electronegative group (important), the leaving group


The electrophilic C can be recognised by looking for the polar σ bond due to the presence of an electronegative substituent (esp. C-Cl, C-Br, C-I and C-O)

Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups.

Of particular importance are the reactions of alkyl halides (R-X) and alcohols (R-OH)

For alcohols, the range of substitution reactions possible can be increased by utilising the tosylates (R-OTs), an alternative method of converting the -OH to a better leaving group.

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37

nucleophilic substitution


1. How can an electrophilic saturated C atom can be recognised?

 

What does the term "nucleophilic substitution" imply ?

A nucleophile is an electron rich species that will react with an electron poor species
A substitution implies that one group replaces another.

Nucleophilic substitution reactions occur when an electron rich species, the nucleophile, reacts at an electrophilic saturated C atom attached to an electronegative group (important), the leaving group


The electrophilic C can be recognised by looking for the polar σ bond due to the presence of an electronegative substituent (esp. C-Cl, C-Br, C-I and C-O)

Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups.

Of particular importance are the reactions of alkyl halides (R-X) and alcohols (R-OH)

For alcohols, the range of substitution reactions possible can be increased by utilising the tosylates (R-OTs), an alternative method of converting the -OH to a better leaving group.

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38

nucleophilic substitution

 

1. Nucleophilic substitution reactions are an important class of reactions that allow the ..?..   of  functional groups

 

What does the term "nucleophilic substitution" imply ?

 

Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups.

Of particular importance are the reactions of alkyl halides (R-X) and alcohols (R-OH)

For alcohols, the range of substitution reactions possible can be increased by utilising the tosylates (R-OTs), an alternative method of converting the -OH to a better leaving group.

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39

nucleophilic substitution

 

Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups.

1. Of particular importance are the reactions of ..?....?.. and ..?..

 

What does the term "nucleophilic substitution" imply ?

 

 

Of particular importance are the reactions of alkyl halides (R-X) and alcohols (R-OH)

For alcohols, the range of substitution reactions possible can be increased by utilising the tosylates (R-OTs), an alternative method of converting the -OH to a better leaving group.

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