Alkyl Halides and Alcohols

Question 1

carbon nucleophiles

Answer 1

Na+-C=_CH3
K+-C=_CN
*negative

Question 2

oxygen nucleophiles

Answer 2

Na+-OH
Na+-OMe
Na+-OEt
*negative
- add H to negative ion to make neutral

Question 3

sulphur nucleophiles

Answer 3

Na+-SCH3
*negative
- add H to negative ion to make neutral

Question 4

nitrogen nucleophiles

Answer 4

NH3
NH2CH3
*neutral, substitution has an intermediate

Question 5

finkelstein nucleophile

Answer 5

Na+-I

Question 6

sterically hindered base nucleophile

Answer 6

K+t-OBu
*eliminates

Question 7

substitution

Answer 7

nucleophile attacks C
*careful of stereochemistry for secondary or tertiary

Question 8

elimination

Answer 8

nucleophile attacks H on Carbon beside C-X
*careful if there’s two products

Question 9

stereochemistry

Answer 9

4 different groups attached to carbon
-nucleophile approaches carbon from opposite side to leaving group

Question 10

markovnikov addition

Answer 10

in a double bond:
H on less substituted C
OH on most substituted C

Question 11

oxygen charge

Answer 11

two bonds - neutral
one bond - negative
three bonds - positive

Question 12

nitrogen charge

Answer 12

three bonds - neutral
two bonds - negative
four bonds - positive

Question 13

substitution vs elimination

Answer 13

substitution major
elimination minor

Question 14

Industrial Large Scale (IPA)
- substrate and product

Answer 14

alkene to alcohol

Question 15

Industrial Large Scale (IPA)
- mechanism

Answer 15

carbon attacks H(of H2SO4)
H2O attacks +C
-O takes back H to form H2SO4

Question 16

Industrial Large Scale (IPA)
- reagent(s)

Answer 16

1) H2SO4
2) H20
*markovnikov addition

Question 17

oxymercuration reaction
- addition type

Answer 17

markovnikov addition

Question 18

oxymercuration reaction
- reagent(s)

Answer 18

1) Hg(OAc)2
2) NaBH4
3) H20

Question 19

oxymercuration reaction
- substrate and product

Answer 19

alkene to secondary alcohol

Question 20

hydroboration oxidation
- addition type

Answer 20

anti-markovnikov

Question 21

hydroboration oxidation
- reagent(s)

Answer 21

1) B2H6
2) H2O2
3) NaOH (aq)

Question 22

hydroboration oxidation
- substrate and product

Answer 22

alkene to primary alcohol

Question 23

dehydration reaction
- substrate and product

Answer 23

alcohol to alkene
-OH poor leaving group, become H2O excellent leaving group

Question 24

dehydration reaction
- reagent(s)

Answer 24

1) H2SO4, attacked by OH
*losing H20, occurs with heat

Question 25

alkyl chloride from primary alcohol - reagent(s)

Answer 25

SOCl2

Question 26

alkyl bromide from primary alcohol - reagent(s)

Answer 26

PBr3 *x3 alcohol -> x3 product

Question 27

alkyl halides from secondary/tertiary alcohol - reagent(s)

Answer 27

HCl or HBr *H+ attacked by OH

Question 28

oxidation table of primary alcohol - products

Answer 28

1. alcohol -> 2. aldehyde -> carboxylic acid

Question 29

oxidation table of secondary alcohol - products

Answer 29

1. alcohol -> 2. ketone

Question 30

oxidation table of alcohols - reagents

Answer 30

alcohol to aldehyde/ketone = PCC alcohol to carboxylic acid = jones reagent aldehyde to carb acid = AgO2

Question 31

PCC

Answer 31

CrO3Cl

Question 32

Jones Reagent

Answer 32

CrO3, H2SO4

Question 33

reduction table of primary alcohol - products

Answer 33

3. carb acid -> 1. alcohol 2. aldehyde -> 1. alcohol * cant go from 3 to 2

Question 34

reduction table of secondary alcohol - products

Answer 34

2. ketone -> 1. alcohol

Question 35

reduction table of alcohols - reagents

Answer 35

carb acid to alcohol = LiAlH4 aldehyde/ketone to alcohol = NaBH4 or LiALH4

Question 36

alkyl halides to thioether - nucleophiles

Answer 36

Na+-SCH3 Na+-SPh *nucleophile attacks C