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OH A) HBr K) Cl2, hv B) NaOH, H2O L) SOCI2 C) CH3COONa, DMF M) LiAlHA, THE D) CH3CH2CH2CH2MgBr, ether N) NaBH4, CHCH2OH E) CH3CH2MgBr, ether O)
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Organic Chemistry

I just wanted to verify that I completed the following questions correctly. If you could please review my work and give explanation if I have incorrect information. Thank you!


Question 1:

Look at the given synthesis and the provided reagents. Fill in the blanks with the single letter codeof the appropriate reagent, or the appropriate descriptive vocabulary word/phrase for non-reagents to complete the synthesis and description. spelling carefully!

Screen Shot 2020-07-29 at 9.12.13 PM.png

-First we add reagent S to form the molecule butane (IUPAC name). 

-Then reagent I to form a bromo functional group in a free radical bromination reaction.

-This can be converted to a functional group hydroxyl by first adding reagent C in a SN2 mechanism then following up with reagent U  to give the desired group via a Ester Hydrolysis reaction.

-A(n) oxidation (oxidation, reduction, substitution, hydrolysis, other) with reagent H will give the functional group carbonyl  , which can be reacted first with F  followed by reagent Q  workup to give the desired product.

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Question 2:

Look at the given synthesis and the provided reagents. Fill in the blanks with the single letter codeof the appropriate reagent, or the appropriate descriptive vocabulary word/phrase for non-reagents to complete the synthesis and description. spelling carefully!

Screen Shot 2020-07-29 at 9.19.06 PM.png

-First we add a(n) base (please help here)  (oxidizing agent, reducing agent, acid, base, electrophile, nucleophile) in the form of reagent B , which will create the functional group alkoxide ion.

-This ion immediately undergoes a addition/elimination mechanisms in a epoxide synthesis to form the functional group epoxide.

-Then addition of reagent P will create two functional groups:

-a tertiary ether 

-and a secondary alcohol.

-Then addition of reagent PCC will form a ketone functional group, which will give the final product upon addition of reagent (please help here) and reagent (please help here) workup.

Screen Shot 2020-07-29 at 9.12.13 PM.png
OH
A) HBr
K) Cl2, hv
B) NaOH, H2O
L) SOCI2
C) CH3COONa, DMF
M) LiAlHA, THE
D) CH3CH2CH2CH2MgBr, ether N) NaBH4, CHCH2OH
E) CH3CH2MgBr, ether
O) CH3CH2OH, H2SO4
F) CH3CH,Li, ether
P) CH3CH2ONa, CH3OH
G) Cro3, H2SO4, H2O
Q) HaOt
H) PCC, CH2CI2
R) PBr3
1) Br2, hv
S) H2, Pd
J) heat
T) CHCH2CH2CH2OH, heat
U) H20, H2SO4
Screen Shot 2020-07-29 at 9.19.06 PM.png
Br
HO
HO
OCH2CH3
A) HBr
K) Cl2, hv
B) NaOH, H2O
L) SOCI2
C) CH3COONa, DMF
M) LiAIHA, THE
D) CH3CH2CH2CH2MgBr, ether N) NaBH4, CHCH2OH
E) CH3CH2MgBr, ether
O) CH3CH2OH, H2SO4
F) CHCH,Li, ether
P) CH3CH2ONa, CH3OH
G) Cro3, H2SO4, H2O
Q) HaO
H) PCC, CH2Cl2
R) PBr3
1) Br2, hv
S) H2, Pd
J) heat
T) CH3CH2CH2CH2OH, heat
U) H20, H2SO4

Step-by-step answer

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