Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 16, Problem 16.60P
(a)
Interpretation Introduction
Interpretation:
The given reactions are final steps in one industrial synthesis of vitamin A acetate.
The mechanism has to be proposed for the acid-catalyzed cyclization in step-1.
Concept Introduction:
The ring cyclization occurs when an acyclic molecule reacts with acid. by the abstraction of proton from the acid molecule, internal bond shifting occurs to form the cyclization product.
(b)
Interpretation Introduction
Interpretation:
The given reactions are final steps in one industrial synthesis of vitamin A acetate.
The reagents has to be given for the reaction involved in step-2.
(c)
Interpretation Introduction
Interpretation:
The given reactions are final steps in one industrial synthesis of vitamin A acetate.
The mechanism has to be proposed for the formation of phosphonium salt in step-4.
(d)
Interpretation Introduction
Interpretation:
The given reactions are final steps in one industrial synthesis of vitamin A acetate.
The reagents that are involved in the reaction of step-3 has to be proposed.
(e)
Interpretation Introduction
Interpretation:
The given reactions are final steps in one industrial synthesis of vitamin A acetate.
Wittig reaction of step-5 has to be shown.
Concept Introduction:
Wittig reaction:
The reaction of carbonyl compound with the ylide of phosphonium salt to give an
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
In the Thermo Fisher application note about wine analysis (Lesson 3), the following
chromatogram was collected of nine components of wine. If peak 3 has a retention time of
3.15 minutes and a peak width of 0.070 minutes, and peak 4 has a retention time of 3.24
minutes and a peak width of 0.075 minutes, what is the resolution factor between the two
peaks? [Hint: it will help to review Lesson 2 for this question.]
MAU
300
200
T
34
5
100-
1 2
CO
6
7
8
9
0
2.4
2.6
2.8
3.0 3.2 3.4
3.6
3.8 4.0 4.2
4.4
4.6
4.8
5.0
5.2
Minutes
3.22
0.62
1.04
O 1.24
The diagram shows two
metals, A and B, which melt at
1000°C and 1400°C. State the
weight percentage of the
primary constituent (grains of
C) that would be obtained by
solidifying a 20% alloy of B.
1000°C
a+L
L+C
900°С
12
α
a+C
45
1200 C
L+y
140096
C+Y
a+ß
800°C
700°C
C+B
96
92
a+B
0
10
20
30
40
50
60
70 80 90 100
A
% peso B
B
8.
Choose the compound that will produce the spectrum below and assign the signals to the corresponding
protons.
2
4
3
ō (ppm)
OH
4
6 6
СОН
2
1
0
Chapter 16 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 16.1 - Write the IUPAC name for each compound. Specify...Ch. 16.1 - Write structural formulas for all aldehydes with...Ch. 16.1 - Write the IUPAC name for each compound.Ch. 16.5 - Prob. 16.4PCh. 16.6 - Prob. 16.5PCh. 16.7 - Prob. 16.6PCh. 16.7 - Write a mechanism for the acid-catalyzed...Ch. 16.8 - Prob. 16.8PCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...
Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
Knowledge Booster
Similar questions
- 7. Assign all of the protons on the spectrum below. A B 2 C E 2 1 3 6 4 3 2 1 0arrow_forwarde. If (3R,4R)-3,4-dichloro-2,5-dimethylhexane and (3R,4S)-3,4-dichloro-2,5-dimethylhexane are in a solution at the same concentration, would this solution be expected to rotate plane polarized light (that is, be optically active)? Please provide your reasoning for your answer. [If you read this problem carefully, you will not need to draw out the structures to arrive at your answer...]arrow_forward1. How many neighbors does the proton that produces the multiplet below have? 2. 3. اللـ Draw a partial structure from the multiplet below. (The integration of the multiplet is 6) M Using the additivity constants found in appendix G of your lab manual, calculate the approximate chemical shifts of the protons indicated below. (Show your work!!!) B A Br SHarrow_forward
- 1) Suppose 0.1 kg ice at 0°C (273K) is in 0.5kg water at 20°C (293K). What is the change in entropy of the ice as it melts at 0°? To produce the original "water gas" mixture, carbon (in a combustible form known as coke) is reacted with steam: 131.4 kJ + H20(g) + C(s) → CO(g) + H2(g) From this information and the equations in the previous problem, calculate the enthalpy for the combustion or carbon to form carbon dioxide. kindly show me how to solve this long problem. Thanksarrow_forward4. An 'H-NMR of a compound is acquired. The integration for signal A is 5692 and the integration for signal B is 25614. What is the simplest whole number ratio of protons for signals A and B? (Show your work!!!) 5. Assign the carbons in the NMR below as either carbonyl, aromatic, or alkyl. 200 150 100 50 ō (ppm) 1arrow_forwardSpeaking of composite materials, indicate the correct option:(A). Composite materials can only be: metal-polymer or polymer-polymer.(B). Composite materials can be made up of particles, but not fibers or sheets.(C). When the reinforcing particles are uniformly distributed in a composite material, there may be a greater tendency for it to have isotropic properties.(D). None of the above is correct.arrow_forward
- If we are talking about viscoelastic modulus or viscoelastic relaxation modulus in polymers, indicate the correct option.(A). It reports the variation of elastic behavior as a function of time.(B). It is only useful for defining its glass transition temperature.(C). It only allows us to define the polymer degradation temperature.(D). Neither option is correct.arrow_forwardWhen natural light falls perpendicularly on a material A, it has a reflectivity of 0.813%. Indicate the value of the refractive index.arrow_forwardIn piezoelectricity and piezoelectric ceramics, one of the following options is false:(A). Piezoelectricity allows an electrical signal to be transformed into a mechanical one.(B). PbZrO3 is a well-known piezoelectric ceramic.(C). Piezoelectricity and ferroelectricity in general have no relationship.(D). One of the applications of piezoelectricity is sonar.arrow_forward
- (30 MARKS) Give the major product(s ) formed including relevant stereochemistry or the complete reaction conditions for the following reactions. More than one step may be required for each reaction arrow, in which case the steps must be numbered 1), 2) etc. (2 marks each box) h) i) h) OH i) HO H3PO4, heat 2 Brarrow_forwardNonearrow_forwardIndicate which option is false(A). Resistivity has a residual component and a thermal component.(B). In some materials resistivity increases with T and in others it decreases.(C). In insulating materials, resistivity is very low.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning