Chapter 8

Question 1

Addition of halogens/dihalogenation

Answer 1

Form: compound + X2 ->CH2Cl2

What happens:
Intermediate: 3 members ring forms in double bond with positively charged halogen
Final: 2 halogens on either side of double bond, trans if in ring

Relationship:
50/50 Enantiomer
Racemic mixture

Question 2

Halohydrin addition of HOX

Answer 2

Form: ->X2,H2O HX
Product:OH to more substituted side trans to X
Relationship:50/50 Enantiomer if no other chiral center
If another chiral center is present the. Diastereomer

Question 3

Alkene hydration

Answer 3

Form:->H3O
Product: follow markovinokov with OH
IF CARBOCATION(OPPOSITE OF H) IS ON PRIMARY CARBOCATION HYDRIDE SHIFT TO SECONDARY WITH OH
Relationship: Racemetic unless no chiral centers then one product

Question 4

Oxymercuration

Answer 4

Form: ->Hg(OAc)2, H2O/NaBH4
Product: OH follows Markovinokov
No carbocation shift
Relationship: enentiomers unless no chiral centers then 1 compound or 2 chiral centers then diasteomers

Question 5

Hydroboration

Answer 5

Form: BH3
Product: anti markovinokov oh, oh and h cis no carbocation shift
Relationship: enentiomers unless no chiral centers then 1 compound or 2 chiral centers then diasteomers

Question 6

Reduction of Alkenes

Answer 6

Form:H2 Pd//\OH
Product: eliminate all double bond place hydrogens cis
Relationship: racemic mixure

Question 7

Simmons smith reaction

Answer 7

Form:+CH2I2. Zn,Cu/ether, KOH
Product: double bond replaced with 3 members ring with ch2 on outside of compound before is cis then ring is cis if trans then trans
If koh then use whatever comes before it in ring CHCl3 carbon in ring and 2Cl coming off
Relationship: Racemetic

Question 8

Epoxidation of Alkenes

Answer 8

Form: mcpba or R-c=o-o-o-h
Product: three membered ring with o on the end if molecule is cis the. Ring is cis if molecule is trans ring is trans
Relationship: if trans Racemetic if cis identical

Question 9

Epoxidation then hydration

Answer 9

Form: mcpba H3O
Product: replace double bond with trans oh on each side
Relationship: Enantiomer

Question 10

Carbocation stability

Answer 10

Count number of carbons that connect to cation
Least carbons is least stable
If resonance is possible then most stable

Question 11

Oxidation

Answer 11

Form: OsO4,H2O/NaHSO3
Product: cis OH coming off double bond with opposite R groups
If compound is cis then meso compound is formed
Relationship:
If molecule is cis then meso
If chiral the. Racemetic

Question 12

Ozoneolysis

Answer 12

Form:O3
Product: double bond breaks and forms 3 O double bonds
Relationship:

Question 13

Ozoneolysis by KMnO4

Answer 13

Form:KMnO4
Product: double bonds breaks and forms 2 O double bonds terminal ch bonds turn into C-OH bonds
Relationship:

Question 14

Electrophillic addition

Answer 14

Form:HX
Product: halogen follows markovinokov rule
Relationship: stereochemistry not considered