Mcat Organic Chemistry

Front 1

Name the three IUPAC Rules for nomenclature.

Back 1

1) Longest carbon chain with the most substituents determines the base name
2) The end carbon closest to a carbon with a substituent is the first carbon
3) Order substituents alphabetically

Front 2

How do you calculate hybridization?

Back 2

= # of lone pairs of electrons + # of sigma bonds
-divide the number above over the s (max 1), p (max 3) and d(max 5) orbitals

Front 3

What shape(s) is(are) affliated with an sp hybridization?

Back 3

Linear

Front 4

What shape(s) is(are) affliated with an sp2 hybridization?

Back 4

Trigonal Planar

Front 5

What shape(s) is(are) affliated with an sp3 hybridization?

Back 5

Tetrahedral (4 bonds), Pyramidal (3 bonds), Bent (2 bonds)

Front 6

What shape(s) is(are) affliated with an dsp3 hybridization?

Back 6

Trigonal bypyramidal (5 bonds), Seesaw, T shaped, Linear

Front 7

What shape(s) is(are) affliated with an d2sp3 hybridization?

Back 7

Octahedral, Square Pyramidal, Square Planar

Front 8

What is the number of stereoisomers that a compound can have?

Back 8

=2^n
n= # of chiral carbons

Front 9

What are the rules for determining absolute configuration?

Back 9

Atoms numbers from highest to lowest priority
1) Largest Atomic Weight given precedence (of first atom of substituent)
-if two substituents have same element, look to the next element on the chain
-double and triple bonds are counted twice and thrice, respectively
2) Face lowest priority group away
3) Look to see which direction takes the atoms from highest priority to lowest
-R= clockwise
-S= counterclockwise

Front 10

For observed rotation, what two symbols indicate that the compound rotates clockwise?

Back 10

+ and d

Front 11

For observed rotation, what symbols indicate that the compound has rotated counterclockwise?

Back 11

"-" and l

Front 12

What is a Meso Compound?

Back 12

A compound that is a mirror image of itself (and thus has no observed rotation)

Front 13

What is an Enantiomer?

Back 13

Two molecules possessing the same molecular formula, same bond to bond configuration and are mirror images

Front 14

What are diastereomers? Give one example.

Back 14

Two molecules possessing the same molecular formula, same bond to bond configurations but are not mirror images.
Example: Geometric Isomers (Cis, Trans Isomers)

Front 15

Name the four reactions involving the creation of an Alkene.

Back 15

1) Elimination
2) Wittig Reaction
3) Condensation of Amine with Ketone
3)Hofmann Elimination

Front 16

Distinguish the conditions required for Elimination via an E1 mechanism opposed to an E2 mechanism.

Back 16

E1: Weak base or hot concentrated acid
E2: Strong, Bulky base
-bulkiness prevents Sn2

Front 17

What is Saytzeff's Rule?

Back 17

The major product of an elimination will be the most substituted alkene.

Front 18

Name the reactants of the Wittig Reaction.

Back 18

Phosphorous Ylide
Ketone or Aldehyde

Front 19

Name the products of the Wittig Reaction.

Back 19

An alkene with cis/trans isomerism.

Front 20

Name the products of Amine Condensation with Aldehyde/Ketone if:
1) A primary amine is used
2) A secondary amine is used.

Back 20

1) Imine (has C with N double bonded to an R group)
2) Enamine (has C double bonded to adjacent C. The first C is also bonded to a secondary amine).

Front 21

What are the reactants and conditions involved in the Hofmann Elimination?

Back 21

Quaternary Amine
Heat + OH-

Front 22

What is a Hofmann product?

Back 22

When the alkene forms on the less substituted carbon (least stable alkene).

Front 23

What is the order of carbocation stability?

Back 23

3 > 2 > 1 > methyl

Front 24

How do you reduce an alkene?

Back 24

Add H2 in the presence of a heterogenous catalyst.

Front 25

What is a heterogenous catalyst? (3)

Back 25

A catalyst that is in a different phase from its substrate.
Ni
Pd
Pt

Front 26

How do you oxidize an alkene? What is the product if you use an alkene? Alkyne?

Back 26

Ozone (O3) with Zn and H2O
Product: carbonyl group (alkene), carboxilic acid (alkyne)

Front 27

Name the four major types of reaction where an alkene is the reactant.

Back 27

1) Reduction
2) Oxidation
3) Addition
4) Halogenation (of an alkene)

Front 28

Oxymercuration/Demercuration, Hydroboration and Hydration of an Alkene are all examples of what?

Back 28

Addition

Front 29

What is the purpose of an addition reaction?

Back 29

To transform an Alkene into an Alkane, and add a substituent.

Front 30

What type of reactant is required for an Addition to occur?

Back 30

Electrophile

Front 31

What is an electrophile?

Back 31

A compound containing either a full or partial positive charge. Attacks a double bond in Addition reactions.

Front 32

What is Markovnikov's Rule?

Back 32

Hydrogen (electrophile) will attach to the least substituted carbon.

Front 33

When this acid is used, Anti Markovnikov addition occurs. What is the acid and what is anti-markovnikov addition?

Back 33

HBr in the presence of peroxides.
Br adds to the least substituted carbon (instead of H)

Front 34

What is the Hydration of an Alkene? What type of reaction is it? What conditions must be present?
What kind of Addition is this?

Back 34

1) The transformation of an alkene into an alcohol
2) Addition
3) Hot, concentrated acid
4) Markovnikov

Front 35

What conditions are required to dehydrate an alcohol? What is the product?

Back 35

1) Cold, dilute acid
2) Alkene

Front 36

When will Anti-Markovnikov Addition occur?

Back 36

If HBr used in presence of peroxides.

Front 37

What is the purpose of an Oxymercuration/Demercuration?

Back 37

To make an alcohol out of an alkene

Front 38

What are the reactants used in Oxymercuration/Demercuration?

Back 38

1) Alkene
2) Hg(OAc)
3) H2O
4) NaBH4 (get one alcohol for each hydrogen)

Front 39

What is the product of an Oxymercuration Demercuration? What type of addition is it?

Back 39

An Alcohol in accordance with Markovnikov's Rule.
Anti-addition

Front 40

What is Anti addition?

Back 40

When the different parts of the molecule being added in an addition reaction are added to opposite sides of the compound.

Front 41

What is the purpose of Hydroboration?

Back 41

To make an alcohol out of an alkene

Front 42

What are the reactants and conditions used in Hydroboration (4)?

Back 42

1)Alkene
2) Hydrogen Peroxide (H2O2)
3) BH3
4) Basic conditions

Front 43

What kind of addition occurs in Hydroboration?

Back 43

Anti Markovnikov
Syn Addition

Front 44

What is the product of an Halogenation of an Alkene? What kind of addition is this?

Back 44

Vic Dihalide (halides side by side)
Anti Addition/ Markovnikov

Front 45

What is the difference in the type of nucleophile used in Sn1 and Sn2 reactions

Back 45

Sn1= no effect
Sn2= strong nucleophile

Front 46

What is the difference in the substrate used by Sn1 and Sn2

Back 46

Sn1= tertiary
Sn2= methyl, primary, secondary

Front 47

What is the difference in the solvent used in Sn1 and Sn2

Back 47

Sn1= polar protic (hydrogen bonding)
Sn2= polar, aprotic (non hydrogen bonding)

Front 48

What is the difference in the reaction rate of Sn1 and Sn2?

Back 48

Sn1= dependant only on substrate
Sn2= dependant on nucleophile and substrate

Front 49

What is the difference in the stereochemistry of the products formed from Sn1 and Sn2?

Back 49

Sn1- racemic mixture
Sn2- inversion of configuration

Front 50

The products of Sn1 are capable of ____ and _______

Back 50

Skeleton Rearrangement
E1 elimination

Front 51

A base is a stronger nucleophile that ___________

Back 51

its conjugate acid

Front 52

How can you avoid having an elimination occur when you want a substitution?

Back 52

Use a less bulky nucleophile

Front 53

What are two factors that add to nucleophilicity?

Back 53

Negative Charge
Polarizability

Front 54

What makes a good leaving group?

Back 54

The weaker the base, the better the leaving group

Front 55

Name three ways that one can make an alcohol without using an alkene.

Back 55

1) Grignard Synthesis
2) Reduction Synthesis of a Carbonyl
3) Oxidation of an Alkane

Front 56

How is the Grignard Reagent made?

Back 56

RX + Mg ----> RXMG

Front 57

What are the reagents and conditions involved in the Grignard synthesis?

Back 57

RXMg
H3O (Acid)

Front 58

What is the purpose of the Grignard Synthesis?

Back 58

To make a carbonyl into an alcohol and add an alkyl group to the new molecule.

Front 59

What reagents can one use to reduce an aldehyde or a ketone to an alcohol.

Back 59

NaBH4
LiBH4

Front 60

What reagent can one use to reduce a carboxylic acid or an ester into an alcohol?

Back 60

LiH4 only

Front 61

What type of condition must be present for the reduction synthesis of an alcohol?

Back 61

Acidic

Front 62

An alcohol (protonated) is a good _______.

Back 62

Nucleophile.

Front 63

A deprontonated alcohol (O-) is a good
________.

Back 63

Leaving group

Front 64

K2Cr2O7
KMnO4
H2CrO4
O2
Br2
Are all good examples of?

Back 64

Oxidizing Agents

Front 65

LiH4
NaH4
H2 + pressure
Are all good examples of what?

Back 65

Reducing agents

Front 66

The oxidation of an alkane produces what?

Back 66

An alcohol

Front 67

The oxidation of an alcohol produces what?

Back 67

An aldehyde

Front 68

What type of reaction is the formation of an alkyl halide from an alcohol?

Back 68

Substitution
Alcohol= leaving group

Front 69

What is a Pinacol Rearrangement?

Back 69

The dehydration of an alcohol resulting in an unexpected product.

Front 70

When does a pinacol rearrangement occur?

Back 70

When a vinicial alcohol (two OH groups side by side) is treated with hot acid

Front 71

What is the expected product of a pinacol rearrangement?

Back 71

An alkene (dehydration of alcohol).

Front 72

What is the actual product of a pinacol rearrangement?

Back 72

A ketone.
Methyl group shifts overy from carbonyl (carbocation stability).

Front 73

What is an epoxide?

Back 73

A highly reactive ether ring. Reactivity due to ring strain.

Front 74

How can one cleave an ether?

Back 74

Using a halogen in the presence of acid.

Front 75

What are the products of ether cleavage by a halogen?

Back 75

An alcohol and an alkyl halide

Front 76

What type of reactions do Aldehydes and Ketones undergo?

Back 76

Nucleophilic Addition

Front 77

Name the five reactions involving an aldehyde or a ketone as a reactant.

Back 77

1) Aldol Condensation
2) Formation of Acetals
3) Halogenation of Ketone
4) Haloform Reaction
5) Wittig Reaction

Front 78

How are acetals and ketals formed?

Back 78

By placing an aldehyde/ketone in an alcoholic solvent.

Front 79

What is an acetal/ketal?

Back 79

Ethers formed by the placement of aldehydes and ketones in alcohol

Front 80

If an aldehyde or ketone is placed in water, what is the result?

Back 80

A vicinial alcohol

Front 81

What are hemiacetal rings used for?

Back 81

To protect aldehydes from nucleophilic attack.

Front 82

What is an aldol?

Back 82

Aldehyde + Alcohol

Front 83

From what reagents is an aldol created?

Back 83

Two aldehydes.

Front 84

When a ketone is halogenated, to which carbon atom does the halogen attach? What happens to the carbonyl.

Back 84

alpha-carbon
carbonyl stays put

Front 85

If a carbonyl is part of a conjugated system, where does the halogen attach in aldehyde/ketone halogenation

Back 85

beta carbon

Front 86

During aldehyde/ketone halogenation for many halogen atoms add to the aldehyde/ketone?

Back 86

One

Front 87

What is the purpose of the Haloform reaction?

Back 87

To transform a ketone into a carboxylic acid + haloform.

Front 88

What conditions are required for the Haloform reaction?

Back 88

Halogen
Base

Front 89

What are the differences in conditions between the haloform reaction and ketone/aldehyde halogenation?

Back 89

A base is used in the haloform reaction

Front 90

Can aldehydes undergo haloform? Why?

Back 90

No
Decarboxylation of methyl group next to carbonyl occurs

Front 91

How many moles of halogen are required for haloform?

Back 91

3

Front 92

What is the purpose of the Wittig Reaction?

Back 92

To turn a ketone into an alkene while adding an R group.

Front 93

What is Decarboxylation? For what type of molecule does it work?

Back 93

The removal of a CO2.
Works well for molecules where the beta carbon is a carbonyl (ketone, carboxylic acid).

Front 94

What reagents can be used to form an Acyl Chloride?

Back 94

SOCl2
PCl3
PCl5

Front 95

What is made when an alcohol is added to an acyl chloride?

Back 95

Ester

Front 96

What is made when a primary amine is added to an acyl chloride?

Back 96

An Amide

Front 97

What is made what a carboxylic acid is added to an acyl chloride?

Back 97

Anhydride

Front 98

What happens when water is added to an acyl chloride?

Back 98

The acyl chloride reconverts to a carboxylic acid

Front 99

What happens when water is added to an ester, an amide or an anhydride?

Back 99

They all reconvert to a carboxylic acid.

Front 100

What type of reaction do carboxylic acids undergo most frequently?

Back 100

Nucleophilic Substitution

Front 101

What is Transesterification? Under what conditions does it occur?

Back 101

Using an alcohol to change the R group attached to the ether-oxygen of an ester.
Acidic conditions.

Front 102

What is the purpose of the Wolff-Kishner Reduction?

Back 102

To reduce a ketone/aldehyde to an alkane without destroying it.

Front 103

What reagents and conditions are used in the Wolff-Kishner Reduction?

Back 103

Reagent= hydrazine
Conditions: Acid, Base + heat

Front 104

What is the purpose of the alkylation of an amine? What reagent is used?

Back 104

To add an alkyl group to an amine
An alkyl halide is used.

Front 105

What is the purpose of diazotization of an amine?

Back 105

To add a diazonium ion to a primary amine/ aromatic amine using nitrous acid

Front 106

What is a diazonium ion?

Back 106

Two triple bonded nitrogens.