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Organic Chemistry > Exam Two > Flashcards

Exam Two Flashcards

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1
Q

Reactions of 2-Butene with HCl

A

Step 1: the C=C bond attacks partly positive H in HCl, The sec-butyl cation. A 2 degree carbocation intermediate is formed.

Step 2: Chloride ion attacks the sec-butyl cation to form the product, 2-chlorobutane.

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2
Q

What is a carbocation?

A

A species in which a carbon atom has only six electrons in its valence shell and has a positive charge.
They are electrophiles (electron loving)
They are lewis acids

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3
Q

Electrophile

A

A molecule or ion that accepts a pair of electrons to make a new covalent bond. Low electron density species so Electron loving since it seeks a region of high electron density. Lewis acid.

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4
Q

Nucleophile

A

A molecule or ion that donates a pair of electrons to form a new covalent bond. Nucleus loving because it seeks a region of low electron density since it is already a electron rich species. Lewis base

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5
Q

Alkylation of the Acetylide Ion

A

The addition of an alkyl group.

Acetylides ions react with alkyl halides to form internal alkynes. This is an example of alkylation.

KNOW THIS REACTION IN NOTES

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6
Q

Enantiomers

A

Enantiomers are chiral molecules that are mirror images of one another. Furthermore, the molecules are non-superimposable on one another. This means that the molecules cannot be placed on top of one another and give the same molecule.

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7
Q

Achiral

A

Without chirality. No stereocenter. must have one plane of symmetry.

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8
Q

Chiral

A

An object that is nonsuperposable on its mirror image.

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9
Q

Stereocenter

A

Carbon with four different groups bonded to it.

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10
Q

Achiral

A

An object that is superposable on its mirror image.

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11
Q

Transition state

A

Point on the reaction coordinate that the energy is at maximum

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12
Q

Reaction coordinate

A

Horizontal axis. Shows change in position of atoms.

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13
Q

Activation energy

A

The difference in energy between the reactants and the transition state

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14
Q

Reaction intermediate

A

In a two step reaction. unstable species that lies in an energy minimum between two transition states.

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15
Q

Rate determining step

A

The slowest step. the step that crosses the highest energy barrier.

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16
Q

What are some reaction mechanism patterns?

A

Add a proton. remove a proton. reaction of an electrophile and a nucleophile to form a new covalent bond. rearrangement of a bond. break a bond to form a stable ion or molecule.

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17
Q

Exothermic reaction

A

Energy of the products is lower than that of the reactants. Heat is released

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18
Q

Endothermic Reaction

A

Energy of the products is higher than that of the reactants. heat is absorbed.

19
Q

Addition of hydrogen halides ( HCl, HBr, HI)

A

.

20
Q

Markonikov’s Rule

A

The addition of HX to an alkene, hydrogen adds to the doubly bonded carbon that has the greater number of hydrogens already bonded to it.
Hydrogen goes towards the most hydrogens.

21
Q

Regioselective

A

Reaction in which one direction of bond forming or breaking occurs in preference to all other directions.

22
Q

Carbocation

A

A species containing a carbon atom with only three bonds to it and bearing a positive charge. All are lewis acids and electrophiles.

3 degree carbocation is more stable and requires a lower activation energy for its information than a 2 degree. a 2 degree in turn is more stable and requires a lower activation energy than a 1 degree.

23
Q

Alkene

A

Carbo carbon double bond. Unsaturated. Shape is 120 degree angle.

24
Q

Alkyne

A

Unsaturated hydrocarbon that contains a carbon-carbon triple bond.

25
Q

Arene

A

Compound containing one or more benzene rings. Benzene ring is not chemically reactive under any of the conditions in chapters 4-8.

26
Q

What kind of bond does a carbon-carbon double bond consist of?

A

One sigma and one pi bond formed by the overlap of sp^2 hybrid orbitals, and one pi bond formed by the overlap of parallel 2p atomic orbitals.

27
Q

Rotation about the carbon-carbon double bond in ethylene is restricted

A

Because there is such a large energy barrier.

28
Q

What is cis-trans isomerism

A

Isomers that have the same order of attachment of their atoms, but a different arrangement of their atoms in space due to the presence of either a ring or a carbon carbon double bond.

Remember that the two compounds cannot be converted into one another at room temperature because of the restricted rotation about the double bond. They are different compounds with different physical and chemical properties.

29
Q

Which is more stable: Cis or trans?

A

Trans

30
Q

What is Z?

A

groups of higher priority on the carbons of a double bond are on the same side

31
Q

What is E?

A

Groups of higher priority on the carbons of a double bond are on opposite sides

32
Q

What are the priority rules?

A

The higher the atomic number, the higher the priority.

33
Q

It is not possible to have ____ configuration in cycloalkenes of seven or fewer carbons because of angle strain.

A

Trans. So, all are cis.

34
Q

What are the physical properties of alkenes and alkynes?

A

They are nonpolar compounds. the only forces between them are dispersion forces.

Those that are liquid at room temperature are less dense than water. (less than 1.)

They dissolve in each other and in nonpolar organic solvents

They are insoluble in water

35
Q

Regioselectivity

A

A reaction that one direction of bond forming or bond breaking occurs in preference to all other directions.

36
Q

Meso Compounds

A

an achiral compound possessing two or more stereocenters.

37
Q

optical activity

A

ability to rotate the plane of polarized light. optically active if it has chiral centers and not enantiomers.

38
Q

plane polarized

A

light vibrating only in parallel planes

39
Q

dextrorotatory

A

rotating the plane of polarized light in a polarimeter to the right

40
Q

levorotatory

A

rotating the plane of polarized light in a polarimeter to the left.

41
Q

specific rotation

A

observed rotation of the plane of polarized light when a sample is placed in a tube 1 dm long at concentration of 1g/ml

42
Q

racemic mixture

A

equal amount mixture of two enantiomers.

43
Q

What are the properties of stereoisomers?

A

Enantiomers have identical physical and chemical properties in achiral environments.

Diastereomers have different physical and chemical properties.

44
Q

acidity of terminal alkynes?

A

weakly acidic

Organic Chemistry (3 decks)

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