ffad95919b
5
Organic Chemistry I Problem Set 20 Answer Key Alkene Reactions – Practice Exam I. Select the Best Answer _a__ 1. a. b. c. d. e. _b__ 2. a. b. c. d. _c__ 3. a. b. c. d. e. _c__ 4. a. b. c. d. e. CH 3 HI CH 3 I CH 3 I H H CH 3 H H I CH 2 I No Rxn CH 3 CH 3 H 2 Pt CH 3 H H CH 3 CH 3 CH 3 H H H CH 3 CH 3 H All of these are formed 2-methyl-2-butene HBr ROOR Major Product CH 2 C CH 2 CH 3 CH 3 Br OR CH 3 C CH 2 CH 3 CH 3 Br CH 3 CH CH CH 3 CH 3 Br CH 2 C CH 2 CH 3 CH 3 Br Br CH 2 CH CH 2 CH 3 CH 3 Br cyclohexene cold dil KMnO 4 OH - / H 2 O OH H OH H H OH OH OH H H OH OH O
-
Upload
preeti-gunthey-diwan -
Category
Documents
-
view
8 -
download
2
description
f
Transcript of ffad95919b
-
Organic Chemistry I Problem Set 20 Answer Key
Alkene Reactions Practice Exam I. Select the Best Answer _a__ 1. a. b. c. d. e. _b__ 2. a. b. c. d. _c__ 3. a. b. c. d. e. _c__ 4. a. b. c. d. e.
CH3HI
CH3
I
CH3
I
H
H
CH3
H
H
I
CH2I No Rxn
CH3
CH3
H2
Pt
CH3
H
HCH3
CH3
CH3
HH
H
CH3
CH3H
All of theseare formed
2-methyl-2-buteneHBr
ROORMajor Product
CH2CCH2CH3
CH3
Br
OR
CH3CCH2CH3
CH3
Br
CH3CHCHCH3
CH3 Br
CH2CCH2CH3
CH3
Br
Br
CH2CHCH2CH3
CH3
Br
cyclohexenecold dil KMnO4
OH- / H2O
OH
H
OH
H
HOH
OH
OH
HH
OH
OHO
-
_d__ 5. a. b. c. d. e. _c__ 6. _d__ 7. _a__ 8. a. b. c. d. e. _b__ 9. _c__ 10. a. b. c. d. e.
propyleneH2SO4 / H2O
reflux
propylene glycol CH2=C=CH 2 1-propanol 2-propanol none of these
1-butene 1. Hg(OAc)2 / H2O / THF
2. NaBH4Major Product
a. 1,2-butanediol b. 1-butanol c. 2-butanol d. butane
cis-2-butene 1. O32. Zn / H+ / H2O
CH3CHCHCH3
OHOH
CH3CHCH2CH3
OH
CCH3 OH
O
CHCH3
Ob. c. d.a.
2-methylpropeneBr2
CCl4
CH2CCH3
CH3
Br
Br
CH2CHCH3
CH3
Br CCH3
CH3
CH3
Br
CH2CCH3
CH3
Br
CCl3
CH2CCH3
CH3
CCl3
Br
CH3a. B2H6
b. H2O2 / OH- / H2O
a. cis-2-methylcyclohexane b. trans-2-methylcyclohexanol c. 1-methylcyclohexanol
d. 1-methyl-1,2-cyclohexanediol
cis-3-hexeneKMnO4 / H+ / H2O
reflux
CH3CH2CHCHCH2CH3
OHOH
CHCH2CH3
O
CCH2CH3 OH
O
CH2CH2CH3 OH
None of these
-
_d__ 11. a. b. c. d. e. _a__ 12. Major product a. b. c. d. _a__ 13. a. b. c. d. e. _e__ 14. a. b. c. d. e. f. 2 2 _c__ 15.
CH2I2
Zn(Cu)
CH3 CH2II
I
CH3CHCHCH2CH3
CH3Cl KOH
alcohol / heat
CH3
CH3CH2 CH3
H CHCH3
CH3 H
H
CH3
CH3
CH3 CH3
CH3
CCH2
H
H2C CH CH3
CH3
CH3CHCCH2CH3
OHHO
CH3
CH3CCH2CHCH3
OH
CH3
Br
CH3CHCCH2CH3
OHBr
CH3
CH3CHCCH2CH3
OH
CH3
Br
No Rxn
2,3-dimethyl-2-butene1. cold, dil KMnO4
2. HIO4
CH3CCCH3
OHHO
CH3H3C
CH3CCHCH3
OH
CH3
CH3
CH3CCCH3
OH3C
CH3
CHCH3 CH3
OH
CH3CCH3
O
CCH3 C CH3
O
CH3CH3
CH2CCH3
CH3 KOH
CHCl3 / heat
a. 1,2-dimethylcyclopropane b. acetone and CO 2 c. 1,1-dichloro-2-2-dimethylcyclopropane
d. 1-chloro-2-methyl-2-propanol
E-3-methyl-2-penteneBr2 / H2O Major Product
-
_b__ 16. a. b. c. d. e. _c__ 17. a. b. c. d. _c__ 18. a. b. c. d. e. _a__ 19. a. b. c. d.
OH
CH3 H2SO4
heat
OH
OH
CH2OH
cis-2-buteneOsO4
NaHSO3
CHCH3
O
CCH3 OH
OCC
OHHO
CH3H3CHH CCH
HO
H3C
CH3H
OH
propyleneNBS / H2O
DMSO
CHCH3 CH3
OH
CH2CHCH3 OH
Br
CH2CHCH3
OH
Br CH2CHCH3 OH
OH
CH3CH2CH3
CH3HCl
Major Product
CH3
Cl
CH3
H
ClH
CH3
HCl
HCH2Cl
-
CHO
CHO
CHCH2HC
OO
+
II. Answer the following questions: 1. A hydrocarbon of formula C10H14 is treated with ozone, then with acidic zinc in
water. The only products are shown below. Write the structure of the hydrocarbon. 2. A compound of formula C10H16 is treated with ozone, then with acidic zinc in water.
The products of this reaction are shown below. When the original compound is treated with excess H2 / Pt , 1-isopropyl-3-methylcyclohexane is formed. Write the structure of the original compound.
OH2C CCH3 CH2 CH2 CH2 CH C CH3
OO
H O
CH2
CH3
CH3
