Exam 3 Practice test

Question 1

SN2 mechanism/product

Answer 1

Inverted, nucleophile replaced

Question 2

SN1 mechanism/product

Answer 2

Retention and inverstion, nucleophile replaced

Question 3

HX

Answer 3

Halo at mark, syn and anti

Question 4

HBr ONLY, ROOR

Answer 4

Br at anti mark, syn and anti

Question 5

Br2 or Cl2

Answer 5

Anti addn across DB

Question 6

Br2 or Cl2 and H2O

Answer 6

Anti- OH at mark, halo at anti mark

Question 7

H3O+ or H2O

Answer 7

OH at mark, syn and anti

Question 8

1. Hg(OAc)2, H2O
2. NaBH4

Answer 8

OH at mark

Question 9

1. BH3, THF
2. HOOH, NaOH

Answer 9

OH at anti mark across DB, syn

Question 10

1. Hg(OAc)2, MeOH
2. NaBH4

Answer 10

MeO at mark

Question 11

CHX3, KOH

Answer 11

Both ends of DB bind to C, 2X bonded to C, syn

Question 12

CH2I2, ZnCu

Answer 12

Both ends of DB bind to C, 2X bonded to C, syn

Question 13

H2, Pd/C or H2, PtO2

Answer 13

Erases DB

Question 14

RCO3H

Answer 14

DB erase, just bonded to O on both sides (epoxide)

Question 15

H3O+, H2O (epoxide)

Answer 15

Anti addn of OH across DB

Question 16

OH, H2O (Epoxide)

Answer 16

Anti addn of OH across DB

Question 17

1. OSO4
2. NaHSO3, H2O, (Or H2O2)

Answer 17

Syn OH across DB

Question 18

KMnO4 (cold, dilute), OH, H2O

Answer 18

Syn OH across DB

Question 19

HIO4, H2O

Answer 19

OH double bonds to C on both ends, cutting cyclowhatever

Question 20

1. O3
2. Zn (H3O+) or (CH3)2S

Answer 20

OH double bonds to C on both ends, cutting cyclowhatever

Question 21

1. O3
2. H2O2

Answer 21

Adds double bonded O across DB, cutting cyclowhatever. OH added at one end

Question 22

Hot concentrated KMnO4, H3O+, H2O

Answer 22

Adds double bonded O across DB, cutting cyclowhatever. OH added at one endf

Question 23

Bredt’s rule

Answer 23

Can’t have a double bond at a bridgehead carbon if the ring has less than 8 carbons

Question 24

E1 mechanism and product

Answer 24

Leaving group removed, stable products

Question 25

E2 mechanism and product

Answer 25

Leaving group left, stable product plus enantiomer

Question 26

Vinyl

Answer 26

Radical over double bond

Question 27

Allyl

Answer 27

Radical across from double bond

Question 28

Homolytic cleavage

Answer 28

X-X –> 2.X

Question 29

Addition to pi bond

Answer 29

X. + = –> X/.

Question 30

Hydrogen abstraction

Answer 30

X. H-R –> X-H + R.

Question 31

Halogen abstraction

Answer 31

R. X-X –> R-X + X.

Question 32

Elimination

Answer 32

X/. –> X. =

Question 33

Coupling

Answer 33

2X. –> X-X

Question 34

Chlorination of methane

Answer 34

UV light causes homolytic cleavage of Cl2, H bonds to one radical, radical carbon grabs Cl radical, radicals react with each other

Question 35

Where does Br attach to with peroxide?

Answer 35

End of DB

Question 36

Relative reactivity

Answer 36

% yield/#Hs

Question 37

Strongest CH bond

Answer 37

Connected to 2x bond, then 2C away, then 1c

Question 38

NBS

Answer 38

Adds br at mark, forms low concentration of Br2

Question 39

Bromination of DB

Answer 39

NBr broken, radical formed. Br and H form bond, leaving rad on cyclohexane. Then Br2 breaks, adding br to cyclohexane

Question 40

Br2 and HV

Answer 40

BR added to mark

Question 41

KOT HOT

Answer 41

Removes Br, creates db

Question 42

PLEASE KNOW (PAGE 20)