Chapter 6

Question 1

alkyl halide

Answer 1

halogen is directly bonded to an sp3 carbon

Question 2

vinyl halide

Answer 2

halogen is bonded to an sp2 carbon of alkene

Question 3

aryl halides

Answer 3

halogen is bonded to an sp2 carbon on a benzene ring

Question 4

halogens are ______ electronegative than carbon

Answer 4

more

Question 5

methyl halides

Answer 5

halide is attached to a methyl group

Question 6

primary alkyl halide

Answer 6

the carbon to which halogen is bonded, is attached to only one carbon

Question 7

secondary alkyl halide

Answer 7

halogen is attached to a carbon that is secondary

Question 8

tertiary alkyl halide

Answer 8

halogen is attached to a carbon that is tertiary

Question 9

germinal dihalide

Answer 9

two halogen atoms are bonded to the same carbon

Question 10

vicinal dihalide

Answer 10

two halogen atoms are bonded to adjacent carbons

Question 11

uses of alkyl halides

Answer 11

• industrial and household cleaners
• anesthetics
• freons used in refrigerants and foaming agents
• pesticides

Question 12

greater intermolecular forces, __________ the boiling point

Answer 12

higher

Question 13

spherical shape _________ boiling point

Answer 13

decreases

Question 14

free radical halogenation

Answer 14

• chlorination = mixture of products
• bromination = highly selective

Question 15

free radical allylic halogenation

Answer 15

halogen is placed on a carbon directly attached to the double bond

Question 16

prefix: F

Answer 16

fluoro

Question 17

prefix: Cl

Answer 17

chloro

Question 18

prefix: Br

Answer 18

bromo

Question 19

prefix: I

Answer 19

iodo

Question 20

Alkyl halides have ____ priority when it comes to numbering the direction of the chain

Answer 20

NO

Question 21

when a nucleophile reacts with an electrophile that does not have an empty orbital

Answer 21

substitution reaction

Question 22

in a substitution reaction, we use the _______ of the leaving group to determine reaction rate

Answer 22

stability

Question 23

due to their high electronegativity, _________________ will be the primary leaving groups

Answer 23

alkyl halides

Question 24

increasing carbocation stability

Answer 24

1 < 2 < allylic < bensylic < 3

Question 25

increasing radical stability

Answer 25

1 < 2 < 3 < allylic - benzylic

Question 26

SN2 (full name)

Answer 26

substitution nucleophilic bimolecular

Question 27

SN2 Properties: nucleophile

Answer 27

strong

Question 28

SN2 Properties: leaving group

Answer 28

unsubstituted and strong

Question 29

SN2 Properties: reaction coordinate

Answer 29

transition state

Question 30

SN2 Properties: concerted or stepwise

Answer 30

concerted

Question 31

SN2 Properties: rate

Answer 31

- bimolecular - k[Nu][RX]

Question 32

SN2 Properties: stereochemistry

Answer 32

inversion

Question 33

SN2 nickname

Answer 33

backside attack

Question 34

SN2: order of reactivity

Answer 34

methyl > 1 > 2 (tertiary is impossible)

Question 35

the more -R groups, the more substituted the carbocation, the __________ stable

Answer 35

more

Question 36

SN1 (full name)

Answer 36

substitution nucleophilic unimolecular

Question 37

SN1 Properties: nucleophile

Answer 37

weak

Question 38

SN1 Properties: leaving group

Answer 38

highly unsubstituted

Question 39

what does substituted mean?

Answer 39

more R groups (less H)

Question 40

SN1 Properties: concerted or stepwise

Answer 40

stepwise

Question 41

SN1 Properties: rate

Answer 41

- unimolecular - k[RX]

Question 42

SN1 Properties: stereochemistry

Answer 42

racemic

Question 43

SN1 nickname

Answer 43

soluolysis (common solvents: H2O, ROH, NH3)

Question 44

polar solvents are solvents which contain a _______________

Answer 44

net dipole

Question 45

aprotic polar solvents are solvents that cannot display ______________

Answer 45

hydrogen bonding

Question 46

protic solvents are solvents that display _____________

Answer 46

H bonding

Question 47

Which reactions do we prefer in protic solvents?

Answer 47

SN1 and E1

Question 48

Which reactions do we prefer in aprotic solvents?

Answer 48

SN2 and E2

Question 49

H2O, -OH, and amines (polar protic or aprotic)

Answer 49

polar protic

Question 50

THF, DMSO, DMF, (other achronyms) --> (polar protic or aprotic)

Answer 50

polar aprotic

Question 51

alcohol is __________ with a strong acid as it is a common leaving group

Answer 51

protonated

Question 52

-OTs

Answer 52

Sulfonate Ester --> Tosyl (benzene and methyl)

Question 53

-OMs

Answer 53

Sulfonate Ester --> Mesyl (methyl group)

Question 54

-OTf

Answer 54

Sulfonate Ester --> Triflyl (CF3)

Question 55

molecule that can easily donate electrons

Answer 55

nucleophile

Question 56

molecule that can easily remove a proton

Answer 56

base

Question 57

a negative charge will always be a ___________ nucleophile than its neutral counterpart

Answer 57

stronger

Question 58

the bulkier the substrate, the more ______ and less _________ it is

Answer 58

basic, nucleophilic

Question 59

better size for a better base / nucleophile

Answer 59

aprotic

Question 60

Nucleophilicity in ________ solvents increases as the size of the atom increases.

Answer 60

protic

Question 61

carbocations are stabilized by a phenomenon called _______________

Answer 61

hyperconjucation (adjacent sigma bonds can share electron density with the carbocation)

Question 62

the more substituted the carbocation, the more _______________

Answer 62

stable (1 < 2 < allylic - benzylic < 3)

Question 63

1, 2 hydride shift

Answer 63

occurs when there is a hydrogen located on an adjacent, more stable carbon

Question 64

1,2 alkyl shift

Answer 64

occurs when only small alkyl groups are located on an adjacent, more stable carbon

Question 65

ring expansion occurs only on what size of membered ring?

Answer 65

2, 3 or 5 membered ring ONLY