Chemistry of Alkyl Halides and Alcohols

Question 1

C-O bonds and C-X bonds are considered

Answer 1

polar covelant

Question 2

Which tend to have higher boiling points? Alkyl halides or alcohols? Why?

Answer 2

Alcohols; capable of hydrogen bonding

Question 3

Which can more easily dissolve in water? Alkyl halides or alcohols?

Answer 3

Alcohols. Alkyl Halides cannot dissolve in water.

Question 4

( ) + ( ) -> Alkyl Halide + Water

Answer 4

Alcohol + Hydrogen Halide

Question 5

Order of Reactivity of Hydrogen Halides

Answer 5

HI>HBr>HCl»HF

Question 6

HCl reaction with classes of alcohols

Answer 6

cannot react with primary or secondary alcohols

Question 7

Reaction of an alcohol with a hydrogen halide is called a ___ reaction.

Answer 7

substitution

Question 8

Formation of tert-Butyl Chloride from tert-Butyl Alcohol & Hydrogen Chloride [[Step 1]]

Answer 8

Protonation of tert-Butyl alcohol to give alkyloxonium ion.

Question 9

Formation of tert-Butyl Chloride from tert-Butyl Alcohol & Hydrogen Chloride [[Step 2]]

Answer 9

Dissociaton of tert-butyloxonium ion to give carbocation.

Question 10

Formation of tert-Butyl Chloride from tert-Butyl Alcohol & Hydrogen Chloride [[Step 3]]

Answer 10

Capture of tert-butyl cation by chloride ion.

Question 11

Formation of tert-Butyl Chloride from tert-Butyl Alcohol & Hydrogen Chloride “What is the slow step?”

Answer 11

Step 2: Dissociation of tert-butyloxonium ion to give carbocation.

Question 12

Common functional groups for hydrogen bonding

Answer 12

Alcohols and amines

Question 13

Protic: Formic Acid

Answer 13

H-(C=O)OH

Question 14

Protic: Acetic Acid

Answer 14

Me(C=O)OH

Question 15

Nonpolar Aprotic: Methylene Chloride

Answer 15

CH2Cl2

Question 16

Nonpolar Aprotic: Chloroform

Answer 16

HCCl3

Question 17

Aprotic: THF

Answer 17

(Tetrahydrofuran)5 membered ring with one carbon switched for an oxygen

Question 18

Aromatic Solvents: Toluene

Answer 18

Me-Benzene

Question 19

Aromatic Solvents: Mesitylene

Answer 19

Benzene ring with 3 equidistant methyl groups

Question 20

Aromatic Solvents: Para, Meta, and Ortho Xylene

Answer 20

Sets of 2 methyl substituents off a benzene ring

Question 21

Dipolar Aprotic Solvents: DMF

Answer 21

Dimethyl formamide: H(C=O)N-Me2

Question 22

Dipolar Aprotic Solvents solvate ____ ions better than ___ ions because…

Answer 22

Dipolar Aprotic Solvents solvate “positive” ions better than “negative” ions because the negative side of the dipolar solvents is more accessible and able to surround the cations.

Question 23

Dipolar Aprotic Solvents: Acetone

Answer 23

Me-(C=O)-Me

Question 24

Dipolar Aprotic Solvents: DMSO

Answer 24

Dimethyl sulfoxide: Me-(S=O)-Me

Question 25

_____ tend to be left more ____ in dipolar solvents

Answer 25

Anions tend to be left more naked in dipolar solvents.

Question 26

Reactions with ____ intermediates will go faster in polar solvents

Answer 26

Reactions with ionic intermediates will go faster in polar solvents.

Question 27

Crown Ethers: Naming system

Answer 27

(# of members in ring)-C-(# of non-Carbon members in ring)

Question 28

The ideal usage of crown ethers, is that they can allow ____ solvation of cations.

Answer 28

The ideal usage of crown ethers, is that they can allow differential solvation of cations.

Question 29

Coordinating solvents are considered (polar/nonpolar)

Answer 29

Coordinating solvents are considered polar.

Question 30

In organometallic reagents, the carbon is (electrophilic/nucleophilic)

Answer 30

In organometallic reagents, the carbon is nucleophilic.

Question 31

SN1 Reaction of an Alkyl Halide (name, structure of R-X, Mechanism, Kinetics, Solvent, condition, stereochemistry)

Answer 31

• substitution nucleophilic unimolecular:
• occurs with tertiary halides, and occasionally secondary halides.
• stepwise
• rate=k[R-X]
• polar, protic is okay
• Acidic/Neutral
• No stereochemical inversion

Question 32

SN2 Reaction of an Alkyl Halide

Answer 32

substitution nucleophilic bimolecular:

• occurs with methyl and primary halides, and occasionally secondary halides.
• concerted
• rate=k[R-X][Nu]
• dipolar, aprotic
• basic/neutral
• stereochemical inversion

Question 33

Walden Inversions

Answer 33

If there is stereochemistry in the alkyl halide, the SN2 mechanism will invert the stereochemistry for the product.

Question 34

Alkyl chlorides have _______ boiling point compared to an alkane of the same mass.

Answer 34

Alkyl chlorides have about the same boiling point compared to an alkane of the same mass.

Question 35

Alkyl bromides and alkyl iodides have _______ boiling point compared to an alkane of the same mass.

Answer 35

Alkyl bromides and alkyl iodides have a lower boiling point compared to an alkane of the same mass.

Question 36

The trends between an alkyl halide and an alkane of its same mass boiling point can be described due to:

Answer 36

The trends between an alkl halide and an alkane of its same mass boiling point can be described due to the more powerful Van der Waals forces between large alkanes.

Question 37

The boiling points of alcohols are ______ when compared to other organic compounds due to _____.

Answer 37

The boiling points of alcohols are unusually high when compared to other organic compounds due to hydrogen bonding.

Question 38

(More spherical/more extended) molecules tend to have a higher boiling point.

Answer 38

More extended molecules tend to have a higher boiling point.

Question 39

When determining polar or non polar:

Answer 39

look at the dielectric constant

Question 40

Gringnard Reagent

Answer 40

Form R-Mg-X