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Organic Chemistry I just wanted to verify that I completed the following questions correctly. Thank you!
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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 following molecules: How many different signals would you expect to see in the 1H NMR of the given compounds? (i.e. different chemical shifts)?

Screen Shot 2020-07-29 at 8.57.58 PM.png

i.) Compound A = 9

ii.) Compound B = 6

iii.) Compound C = 4  

iv.) Compound D = 5  

v.) Compound E =  6 

vi.) Compound F = 7

______________________________________________________________________________________________

Question 2:

Look at the following molecules: How many subpeaks would you expect to see due to coupling in the signal of the indicated hydrogen in the 1H NMR? (i.e. multiplicity)

Screen Shot 2020-07-29 at 9.01.23 PM.png

i.) Compound A = 5

ii.) Compound B = 2

iii.) Compound C = 1  

iv.) Compound D = 3  

v.) Compound E =  9 

vi.) Compound F = 5

______________________________________________________________________________________________

Question 3:

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 9.04.15 PM.png

-First we add reagent G  to form the Carbonyl  functional group via oxidation (oxidation, reduction, substitution, hydrolysis, other).

-Then reagent D  is added followed by reagent U  workup to give the alcohol functional group. The carbon-carbon bond forming reagent is a Grignard reagent.

-We then substitute  (oxidize, reduce, substitute, hydrolyze, other) with reagent R to give the final product.

-Reagent  I could also be used in the last step but is more likely to give side products so is not preferred.

Screen Shot 2020-07-29 at 8.57.58 PM.png
Screen Shot 2020-07-29 at 9.01.23 PM.png
Screen Shot 2020-07-29 at 9.04.15 PM.png
Br
OH
A) HBr
K) Cl2, hv
B) NaOH, HO
L) SOCI2
C) CH3COONa, DMF
M) LiAIHA, THE
D) CHgCH2CH2CH2MgBr, ether N) NaBH4, CH&CH,OH
E) CH3CH2MgBr, ether
O) CH3CH2OH, H2SO4
F) CHCH,Li, ether
P) CH3CH2ONa, CH3OH
G) Cro3, H2SO4, H2O
Q) HaO+
H) PCC, CH2CI2
R) PBr3
I) Br2, hv
S) H2, Pd
J) heat
T) CH3CH2CH2CH2OH, heat
U) H20, H2SO4

Step-by-step answer

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