Analyze the provided spectral data. Does the provided data support the preparation of the desired product? Provide an explanation for your answer. Note: reaction of 3.0 mL of 1-octanol , 5.0 mL (5.3 g) of acetic acid, and 25 drops of concentrated sulfuric acid along to form orange oil. (An example is given below using bannana oil the structure of orange oil is also shown)

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section19.9: Crossed Enolate Reactions Using Lda
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Analyze the provided spectral data. Does the provided data support the preparation of the
desired product? Provide an explanation for your answer.

Note: reaction of 3.0 mL of 1-octanol , 5.0 mL (5.3 g) of
acetic acid, and 25 drops of concentrated sulfuric acid along to form orange oil.

(An example is given below using bannana oil the structure of orange oil is also shown)

Orange_PROTON-4.jdf
AJEOL
---- PROCESSING PARAMETERS
dc balance :0: FALSE
sexp_auto : 0.2
trapazoid3 : 0[%] : 80 (%) : 100 [%]
fft : 1
machinephase
dc_correct
---
Ppm
thresh : 5[%) : 1
peak pick : O[Hz]: 0.1 [ppm] : Both : OI
auto reference : 5[]
Filename
Author
Experiment
Sample_id
Solvent
Creation_time
Revision_time
Current_time
- Orange _PROTON-4.jdE
= Adam Nehls
= single_pulse.ax2
= Orange
= CHLOROFORM-D
- 21-JUL-2017 16:14:45
- 22-JUL-2017 14:49:17
= 22-JUL-2017 14:49: 46
Data format
Dim size
Dim title
Dim units
Dimenaions
site
Spactrometer
- 1D COMPLEX
= 13107
- 1H
- [ppm)
- X
- ECS 40O
= JNM-ECS400
Field_strength
X_acq_duration
X_domain
X_freq
X_offset
X points
Xprescans
X_resolution
Xsweep
Irr_domain
Irr freg
Irr_offset
Tri damain
Tri freq
Tri offset
clipped
Mod_return
= 9.389766 [T) (400 [MHz)
= 2.18365952[s]
= 18
= 399.78219838 (Mtz)
= 5 [ppm)
= 16384
= 1
- 0.45794685 [H2)
= 7.5030012 (KH2)
= 1H
= 399.78219838 [MHz)
= 5[ppm)
= 18
= 399.78219838 [MHz]
= 5 [ppm)
= FALSE
= 1
- 256
- 256
Scans
Total_scans
X_90_width
X_acq_time
X_angle
X_atn
X pulse
Irr_mode
Tri modo
= 6.515 (us)
- 2.18365952 [s]
- 45 [deg)
- 2 [dB)
- 3.2575 (us)
= Off
= Off
= FALSE
= 1[s}
- 10
9.0
8.0
7.0
6.0
5.0
4.0
3.0
-10 Dante presat
2.0
1.0
Initial wait
Recvr_gain
Relaxation_delay - 4 (a)
Repetition_time
Temp get
- 6.18365952 [s)
- 19.5(aci
X: parts per Million : 1H
abundance
o's
Transcribed Image Text:Orange_PROTON-4.jdf AJEOL ---- PROCESSING PARAMETERS dc balance :0: FALSE sexp_auto : 0.2 trapazoid3 : 0[%] : 80 (%) : 100 [%] fft : 1 machinephase dc_correct --- Ppm thresh : 5[%) : 1 peak pick : O[Hz]: 0.1 [ppm] : Both : OI auto reference : 5[] Filename Author Experiment Sample_id Solvent Creation_time Revision_time Current_time - Orange _PROTON-4.jdE = Adam Nehls = single_pulse.ax2 = Orange = CHLOROFORM-D - 21-JUL-2017 16:14:45 - 22-JUL-2017 14:49:17 = 22-JUL-2017 14:49: 46 Data format Dim size Dim title Dim units Dimenaions site Spactrometer - 1D COMPLEX = 13107 - 1H - [ppm) - X - ECS 40O = JNM-ECS400 Field_strength X_acq_duration X_domain X_freq X_offset X points Xprescans X_resolution Xsweep Irr_domain Irr freg Irr_offset Tri damain Tri freq Tri offset clipped Mod_return = 9.389766 [T) (400 [MHz) = 2.18365952[s] = 18 = 399.78219838 (Mtz) = 5 [ppm) = 16384 = 1 - 0.45794685 [H2) = 7.5030012 (KH2) = 1H = 399.78219838 [MHz) = 5[ppm) = 18 = 399.78219838 [MHz] = 5 [ppm) = FALSE = 1 - 256 - 256 Scans Total_scans X_90_width X_acq_time X_angle X_atn X pulse Irr_mode Tri modo = 6.515 (us) - 2.18365952 [s] - 45 [deg) - 2 [dB) - 3.2575 (us) = Off = Off = FALSE = 1[s} - 10 9.0 8.0 7.0 6.0 5.0 4.0 3.0 -10 Dante presat 2.0 1.0 Initial wait Recvr_gain Relaxation_delay - 4 (a) Repetition_time Temp get - 6.18365952 [s) - 19.5(aci X: parts per Million : 1H abundance o's
OCH3
orange
но.
honey
oil of wintergreen
Table 1: Common Fragrant Fruit Esters
One of the most general methods for the preparation of esters is acid-catalyzed esterification
(Equation 1). This reaction is an equilibrium process (the reverse reaction is ester hydrolysis),
and product formation can be favored by increasing the concentration of one of the reactants
and/or by removal of the water formed.
H3O*
Fischer Esterification
+ H20
+ R'OH
R
OR'
H2SO4
banana oil synthesis
HO
OH
isoamyl alcohol
(isopentyl alcohol)
isoamyl acetate
(isopentyl acetate)
acetic acid
Transcribed Image Text:OCH3 orange но. honey oil of wintergreen Table 1: Common Fragrant Fruit Esters One of the most general methods for the preparation of esters is acid-catalyzed esterification (Equation 1). This reaction is an equilibrium process (the reverse reaction is ester hydrolysis), and product formation can be favored by increasing the concentration of one of the reactants and/or by removal of the water formed. H3O* Fischer Esterification + H20 + R'OH R OR' H2SO4 banana oil synthesis HO OH isoamyl alcohol (isopentyl alcohol) isoamyl acetate (isopentyl acetate) acetic acid
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