Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question
hw 7 help
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Step 1
Step 2
Step 3"
Transcribed Image Text:Propose an efficient synthesis for the transformation below, utilizing a Wittig Reaction in one of the steps.
Step 1
Step 2
Step 3
![Reactant/reagent List
Enter code (# or letter) in the appropriate boxes.
Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed
CH,X
X,
B
A
D
E
F
G
H
H2
Alcohols: Assume an acid catalyst [H+], or pyridine, is present if needed.
он
HO.
OH
CH,OH
HO
HO,
он
AA
BB
DD
EE
FF
GG
HH
HH2
Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed
Ph
J
K
M
Ph.
Ph
Ph
Ph
Ph
T
U
V
w
Acid Chlorides: Assume AICI, or pyridine is present if needed
Ph
TT
U
UV
ww
XX
YY
Reactant/reagent List
Enter code (# or letter) in the appropriate boxes.
Other Reagents:
21 Br2, FeBr3
22 Mg. Et,0
23 Cl2, AICI3
24 SOCI2, pyridine
43 NANO2, HCI
1 H30* (dilute H2SO4)
or H30*, heat
2 conc. H,SO4, heat
11 PCC in CH,Cl2
12 Na,Cr2O7, H2SO4, H2O
13 BH THF or 9-BBN,
then H2O2, NaOH
14 Hg(OAc)2, H2O, then NaBH, 25 HNO3, H2SO4
15 O3, then Zn, HCI or DMS
16 MCPBA or CH;CO3H
17 Br2, light or NBS, heat
44 CuBr
45 CuCl
3 NaOEt
46 Cul
4 t-BUOK
47 CUCN
26 fuming H,SO4
27 Fe, HCI; then NaOH
48 HBF.
49 H2O, heat
50 H3PO2
5 H2, Pt
6 H2, Lindlar's catalyst
7 Na, NH3
8 LAH or xs LAH, then H20
9 NABH4, CH3OH
10 NaBH,CN, pH 5
28 Zn(Hg), HCI
29 KCN, or KCN + HCN
18 HBr
19 HBr, ROOR
30 CO2, then H30*
20 PBr3
31 (H*].
HO
он
(-H2O)
Grignard, Wittig and Gilman Reagents:
Assume "then H,0" is included if a protonation step is
needed
32 NH, (1 or 2 equiv.)
33 CH;NH2 (1 or 2 equiv)
34 (CH3)½NH (1 or 2 equiv)
35 EINH, (1 or 2 equiv)
36 PHCH,NH2 (1 or 2 equiv).
37 LDA, -78 °C
38 NaH, 25 °C
51
„MgBr
MeMgBr
EtMgBr PhMgBr PHCH;MgBr
G1
G2
G3
G4
G5
NH2
52
CuLi
Me;Culi Et,Culi
Ph,Culi (PHCH2)hCuli
2
39 LIAI(OR);H, then H20
40 DIBAH, then H20
41 Brz. [H3O*]
42 Br2, NaOH
G6
G7
G8
G9
G10
Ph;P=CH2 Ph3P=CHCH3 PhyP=CHCO¿Et PhyP=CHPH
W1
w2
W3
W4](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fbc96294a-6867-4c53-8945-7b1c26d22cf9%2F1b74be4e-0a29-426d-91a2-c1c36a43d973%2F0bnuzt_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Reactant/reagent List
Enter code (# or letter) in the appropriate boxes.
Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed
CH,X
X,
B
A
D
E
F
G
H
H2
Alcohols: Assume an acid catalyst [H+], or pyridine, is present if needed.
он
HO.
OH
CH,OH
HO
HO,
он
AA
BB
DD
EE
FF
GG
HH
HH2
Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed
Ph
J
K
M
Ph.
Ph
Ph
Ph
Ph
T
U
V
w
Acid Chlorides: Assume AICI, or pyridine is present if needed
Ph
TT
U
UV
ww
XX
YY
Reactant/reagent List
Enter code (# or letter) in the appropriate boxes.
Other Reagents:
21 Br2, FeBr3
22 Mg. Et,0
23 Cl2, AICI3
24 SOCI2, pyridine
43 NANO2, HCI
1 H30* (dilute H2SO4)
or H30*, heat
2 conc. H,SO4, heat
11 PCC in CH,Cl2
12 Na,Cr2O7, H2SO4, H2O
13 BH THF or 9-BBN,
then H2O2, NaOH
14 Hg(OAc)2, H2O, then NaBH, 25 HNO3, H2SO4
15 O3, then Zn, HCI or DMS
16 MCPBA or CH;CO3H
17 Br2, light or NBS, heat
44 CuBr
45 CuCl
3 NaOEt
46 Cul
4 t-BUOK
47 CUCN
26 fuming H,SO4
27 Fe, HCI; then NaOH
48 HBF.
49 H2O, heat
50 H3PO2
5 H2, Pt
6 H2, Lindlar's catalyst
7 Na, NH3
8 LAH or xs LAH, then H20
9 NABH4, CH3OH
10 NaBH,CN, pH 5
28 Zn(Hg), HCI
29 KCN, or KCN + HCN
18 HBr
19 HBr, ROOR
30 CO2, then H30*
20 PBr3
31 (H*].
HO
он
(-H2O)
Grignard, Wittig and Gilman Reagents:
Assume "then H,0" is included if a protonation step is
needed
32 NH, (1 or 2 equiv.)
33 CH;NH2 (1 or 2 equiv)
34 (CH3)½NH (1 or 2 equiv)
35 EINH, (1 or 2 equiv)
36 PHCH,NH2 (1 or 2 equiv).
37 LDA, -78 °C
38 NaH, 25 °C
51
„MgBr
MeMgBr
EtMgBr PhMgBr PHCH;MgBr
G1
G2
G3
G4
G5
NH2
52
CuLi
Me;Culi Et,Culi
Ph,Culi (PHCH2)hCuli
2
39 LIAI(OR);H, then H20
40 DIBAH, then H20
41 Brz. [H3O*]
42 Br2, NaOH
G6
G7
G8
G9
G10
Ph;P=CH2 Ph3P=CHCH3 PhyP=CHCO¿Et PhyP=CHPH
W1
w2
W3
W4
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