Using the reagent list, determine the sequence of reagents needed to complete the synthesis below. Br Step 1 Step 2 Step 3 Step 4

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 64AP: The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold...
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Using the reagent list, determine the sequence of reagents needed to complete the synthesis below.
Br
ÓH
Step 1
Step 2
Step 3
Step 4
Transcribed Image Text:Using the reagent list, determine the sequence of reagents needed to complete the synthesis below. Br ÓH Step 1 Step 2 Step 3 Step 4
Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed
CHX
A
B
D
Alcohols
CHOH
AA
BB
DD
EE
FF
G
Ketones, Aldehydes and Epoxides: Assume "then H,O" is included if a protonation step is needed
A A
J
K
L
M
N
P
R
Acid Chlorides: Assume AICI, is present if needed
Grignard and Wittig Reagents: Assume "then H,0" is included if a protonation step is needed
MeMgBr EIMgBr PhMgBr PHCH,MgBr PhyP=CH, PhyP=CHCH, PhyP=CHCO,E Ph,PCH,Ph
G1
G2
G3
G4
W1
w2
W3
W4
Other Reagents:
1H,O' (dilute H,sO)
11 PCC in CH,C
12 Na,CryOr, H,SO, H0
13 BH, THF or 9-BBN, then HO. NaOH
21 Brz. FeBr,
22 Mg. Et,0
23 Cl,. AICI,
24 SOCI, pyridine
25 HNO,, HSO.
26 fuming H,SO,
27 Fe, HCI; then NaOH
2 conc. H,SO., heat
3 NaOEt
4 -BUOK
14 Hg(OAc). H0, then NaBH,
15 O, then Zn, HCI or DMS
16 МСРВА or CH,со,н
17 Brz. light or NBS, heat
5 H. Pt
6 H. Lindlar's catalyst
7 Na, NH,
8 LAH or xs LAH, then H0
9 NaBH, CH,он
10 NaBH,CN, pH 5
18 HBr
28 Zn(Hg), HCI
29 KCN, or KCN + HCN
19 HBr, ROOR
20 PBr,
30 Co, then HO
31 (H*), Ho OH (H,0)
Transcribed Image Text:Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed CHX A B D Alcohols CHOH AA BB DD EE FF G Ketones, Aldehydes and Epoxides: Assume "then H,O" is included if a protonation step is needed A A J K L M N P R Acid Chlorides: Assume AICI, is present if needed Grignard and Wittig Reagents: Assume "then H,0" is included if a protonation step is needed MeMgBr EIMgBr PhMgBr PHCH,MgBr PhyP=CH, PhyP=CHCH, PhyP=CHCO,E Ph,PCH,Ph G1 G2 G3 G4 W1 w2 W3 W4 Other Reagents: 1H,O' (dilute H,sO) 11 PCC in CH,C 12 Na,CryOr, H,SO, H0 13 BH, THF or 9-BBN, then HO. NaOH 21 Brz. FeBr, 22 Mg. Et,0 23 Cl,. AICI, 24 SOCI, pyridine 25 HNO,, HSO. 26 fuming H,SO, 27 Fe, HCI; then NaOH 2 conc. H,SO., heat 3 NaOEt 4 -BUOK 14 Hg(OAc). H0, then NaBH, 15 O, then Zn, HCI or DMS 16 МСРВА or CH,со,н 17 Brz. light or NBS, heat 5 H. Pt 6 H. Lindlar's catalyst 7 Na, NH, 8 LAH or xs LAH, then H0 9 NaBH, CH,он 10 NaBH,CN, pH 5 18 HBr 28 Zn(Hg), HCI 29 KCN, or KCN + HCN 19 HBr, ROOR 20 PBr, 30 Co, then HO 31 (H*), Ho OH (H,0)
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