01403221 -53
!"# $%&'($
1. .
.
.
2.
.
4-methyl-2-pentene
3,6-dimethyl-3-octene
2-pentyl-1-heptene
. 3-methyl-3-heptene
. 1,5-dimethyl-1-cyclohexene
. (E)-3-methyl-2-pentene
CH 3
. CH3CH=CHCH2−C−CH3
CH 3
CH2=CHCH3
CH3
CH2CH2CH2CH3
H3CH2C
H3CH2C
C
.
.
. 2-methyl-3-octene
. 3,4-dimethyl-2-pentene
.
CH2CH2CH2CH3
C
.
H
H3 C
CH3
H3 C
C
H
CH3
H
C
CH3
H
C
C
CH2CH3
. H
.
3. . "# $%% Z
. '"("# )*+,-"# 2 ."/(0#1)."23454),-0#1 ,+6%34758)9#:854
. "# $%% Z
. '"("# )*+,-"# 2 ."/(0)#1 ."23454),-0#1 ,+6%34758)9#:854
. "# $%% cis
4. . -I, -Br, -OH, -CH3 . -OCH3, -OH, -CH2Cl, -CH2CH2OH
. @OH, -NH2, CH2OH, - CH2NH2
5. 3,3-dimethyl-1-butene < 4-methyl-2-pentene < 2-hexene )*+,-E,+05F 3 G")HIH"#J,484,+6%34)0(,5423 6
3-73" 2-hexane )LM4G(7+ 4-methyl-2-pentene )LM4G(N1$%% iso O4P-0#1 3,3-dimethyl-1-butene )LM4G(N1
$%% neo
Cl
6. . CH3CH2CHCH3
Br
.
CH2CH=CH2
.
+
CH3
. CH3CH=CH2
CH=CHCH3
. CH3CH2CH=CH2
OH
. CH3C−CH2CH3
CH3
. KMnO4
T.
U. CH3CH=CHCH3
Cl
7. . CH3CH2CH2−CCH2CH3
O
O
. CH3CH + HCCH2CH3
CH2CH3
.
OH
CH 3
. CH3−CHCH−CH3
I
CH3
1
Br
CH3
.
8.
Pd
. CH3CH=CCH3 + H2
CH3
. CH3CH=CCH3 + Br2
CH3
. CH3CH=CCH3 + O3
CH3
. CH3CH=CCH3 + HBr
CH3
CH3CH2−CHCH3
CH3
Br
CH3CH−CHCH3
Br CH3
O
O
Zn
CH3C−H + CH3CCH3
CH2Cl2
CCl4
H2O
ROOR
. CH3CH=CCH3 + KMnO4
CH3
CH3CH−CHCH3
Br CH3
OH
CH3CH−CHCH3
OH CH3
OH-, ∆
9.
CH3CH−CH3 + Br−
. CH3CH=CH2 + H−Br
CH3CH−CH2
Br
. )4213,)LM4 3°RX [)N9H',+5933$%% E1
CH3
CH3
1. CH3C−CH2CH3
Br
CH3
2. CH3C−CH2CH3 + KOH
CH3C−CH2CH3 + Br−
EtOH
CH3
CH3
CH3C=CHCH3 + CH2=C−CH2CH3
Major product
minor product
10.
E,+ A = CH3CH=CH2
E,+ B = CH3CH−CH3
OH
E,+ D = CH3CH−CH2
Br Br
2
E,+ C = CH3CH=CH2