reagent to complete each reaction. Ignore inorganic byproducts. ++ ye ⠀⠀ U 31. Select to Draw 80 HCI (1 equiv) 6 tv 0 c 56 D F7 F8 Cla (1 equiv) -- Cla (2 equiv) 4 HCI (excess) NaCl (2 equiv) THE F9 F10 F11 F12

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
Section9.8: Alkylation Of Acetylide Anions
Problem 10P
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Question
A common alkyne starting material is shown below. Predict the major product or missing
reagent to complete each reaction. Ignore inorganic byproducts.
+
esc
CI CI
!
F1
143,176
@
F2
#
3
31,
80
F3
Select to Draw
HCI (1 equiv)
DEC
6
$
4
Q
F4
%
5
tv NA
9
F5
A
6
C
F6
&
7
A
B
с
D
F7
*
8
F8
Cla (1 equiv)
Cla (2 equiv)
HCI (excess)
NaCl (2 equiv)
THF
Done
9
F9
-
.
F10
0
F11
27
F12
Transcribed Image Text:A common alkyne starting material is shown below. Predict the major product or missing reagent to complete each reaction. Ignore inorganic byproducts. + esc CI CI ! F1 143,176 @ F2 # 3 31, 80 F3 Select to Draw HCI (1 equiv) DEC 6 $ 4 Q F4 % 5 tv NA 9 F5 A 6 C F6 & 7 A B с D F7 * 8 F8 Cla (1 equiv) Cla (2 equiv) HCI (excess) NaCl (2 equiv) THF Done 9 F9 - . F10 0 F11 27 F12
ka
tab
Cl₂ (1 equiv)
esc
Select to Draw
!
1
Q
³0
F1
543176
@
2
W
F2
#
3
E
31 6
80
Br
F3
$
4
. Br
Ka
Br
Bri
a
F4
R
De 5
%
tv N
0
F5
T
A
6
C
F6
Y
A
&
7
A
B
C
D
F7
U
*
8
DII
FB
Bra (2 equiv)
HBr (excess)
Bra (1 equiv)
HBr (excess)
H₂O₂
(
DD
9
Ⓒ
Done
F9
)
0
F10
O
P
F11
400)
F12
=
[
de
Transcribed Image Text:ka tab Cl₂ (1 equiv) esc Select to Draw ! 1 Q ³0 F1 543176 @ 2 W F2 # 3 E 31 6 80 Br F3 $ 4 . Br Ka Br Bri a F4 R De 5 % tv N 0 F5 T A 6 C F6 Y A & 7 A B C D F7 U * 8 DII FB Bra (2 equiv) HBr (excess) Bra (1 equiv) HBr (excess) H₂O₂ ( DD 9 Ⓒ Done F9 ) 0 F10 O P F11 400) F12 = [ de
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