Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Textbook Question
Chapter 17.16B, Problem 17.41P
Predict the products formed when m-cresol (m-methylphenol) reacts with
- a. NaOH and then ethyl bromide
- b. bromine in CCl4 in the dark
- c. excess bromine in CCl4 in the light
- d. sodium dichromate in H2S04
- e. two equivalents of tert-butyl chloride and AlCl3
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Solution
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Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag
the appropriate image to the correct position in the reactions.)
Route 1
Aldehyde 1
or
+98
Aldehyde 2
Route 2
Q6
+100
Solved in 1 attempt
Q7
+95
Solved in 2 attempts
Q8
+98
Unlimited attempts
possible
+
+
Grignard 1
OH
H3O+
Grignard 2
Answer Bank
Q9
+90
MgBr
Unlimited attempts
possible
CH3CH2CH2MgBr
Q10
Unlimited attempts
Q11
?
?
+100
in 1 attempt
2-methyl-3-hexanol
CH3CH2MgBr
H
H
о
H
Attempt 3
2) (4 pt) After the reaction was completed, the student collected the following data. Crude
product data is the data collected after the reaction is finished, but before the product
is purified. "Pure" product data is the data collected after attempted purification using
recrystallization.
Student B's data:
Crude product data
"Pure"
product data
after
recrystallization
Crude mass: 0.93 g grey solid
Crude mp: 96-106 °C
Crude % yield:
Pure mass: 0.39 g white solid
Pure mp: 111-113 °C
Pure % yield:
a) Calculate the crude and pure percent yields for the student's reaction.
b) Summarize what is indicated by the crude and pure melting points.
Don't used hand raiting
Chapter 17 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Ch. 17.1 - Prob. 17.1PCh. 17.2 - Prob. 17.2PCh. 17.3 - Prob. 17.3PCh. 17.4 - Use resonance forms to show that the dipolar sigma...Ch. 17.6A - Prob. 17.5PCh. 17.6A - Prob. 17.6PCh. 17.6B - Propose a mechanism for the brommation of...Ch. 17.6B - Prob. 17.8PCh. 17.6B - Prob. 17.9PCh. 17.7 - Prob. 17.10P
Ch. 17.8 - Draw all the resonance forms of the sigma complex...Ch. 17.9 - Predict the mononitration products of the...Ch. 17.9 - Predict the mononitration products of the...Ch. 17.9 - Prob. 17.14PCh. 17.10 - Propose products (if any) and mechanisms for the...Ch. 17.10 - Predict the products (if any) of the following...Ch. 17.10 - Which reactions will produce the desired product...Ch. 17.10 - Prob. 17.19PCh. 17.11C - Prob. 17.20PCh. 17.12A - Prob. 17.21PCh. 17.12B - Propose a mechanism that shows why p-chlorotoluene...Ch. 17.12B - Propose mechanisms and show the expected products...Ch. 17.12B - Prob. 17.24PCh. 17.13A - What products would you expect from the following...Ch. 17.13A - What organocuprate reagent would you use for the...Ch. 17.13B - What products would you expect from the following...Ch. 17.13B - Prob. 17.28PCh. 17.13C - What products would you expect from the following...Ch. 17.13C - Prob. 17.30PCh. 17.14C - Prob. 17.31PCh. 17.14C - Predict the major products of the following...Ch. 17.15A - Predict the major products of treating the...Ch. 17.15B - Prob. 17.34PCh. 17.15B - Prob. 17.35PCh. 17.15B - Predict the major products when the following...Ch. 17.15C - Prob. 17.37PCh. 17.15C - a. Based on what you know about the relative...Ch. 17.15C - Show how you would synthesize the following...Ch. 17.16A - The bombardier beetle defends itself by spraying a...Ch. 17.16B - Predict the products formed when m-cresol...Ch. 17.16B - Prob. 17.42PCh. 17.16B - Prob. 17.43PCh. 17.16B - Predict the site(s) of electophilic attack on...Ch. 17.16B - Prob. 17.45PCh. 17.16B - Prob. 17.46PCh. 17.16B - Propose a synthetic sequence of this...Ch. 17.16B - Prob. 17.48PCh. 17.16B - Starting from toluene, propose a synthesis of this...Ch. 17 - Prob. 17.50SPCh. 17 - Prob. 17.51SPCh. 17 - Show how you would synthesize the following...Ch. 17 - Predict the major products of the following...Ch. 17 - Predict the major products of bromination of the...Ch. 17 - What products would you expect from the following...Ch. 17 - Prob. 17.56SPCh. 17 - Prob. 17.57SPCh. 17 - The following compound reacts with a hot,...Ch. 17 - Prob. 17.59SPCh. 17 - Electrophilic aromatic substitution usually occurs...Ch. 17 - Prob. 17.62SPCh. 17 - The most common selective herbicide for killing...Ch. 17 - Furan undergoes electrophilic aromatic...Ch. 17 - Prob. 17.65SPCh. 17 - Bisphenol A is an important component of many...Ch. 17 - Prob. 17.67SPCh. 17 - Prob. 17.68SPCh. 17 - Prob. 17.69SPCh. 17 - In Chapter14, we saw that Agent Orange contains...Ch. 17 - Phenol reacts with three equivalents of bromine in...Ch. 17 - Prob. 17.72SPCh. 17 - Prob. 17.73SPCh. 17 - A common illicit synthesis of methamphetamine...Ch. 17 - Prob. 17.75SPCh. 17 - Prob. 17.76SPCh. 17 - Prob. 17.77SPCh. 17 - Prob. 17.78SP
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- A DEPT NMR spectrum is shown for a molecule with the molecular formula of C5H12O. Draw the structure that best fits this data. 200 180 160 140 120 100 一盆 00 40 8- 20 ppm 0 Qarrow_forwardDon't used hand raitingarrow_forwardShown below is the major resonance structure for a molecule. Draw the second best resonance structure of the molecule. Include all non-zero formal charges. H. H. +N=C H H H Cl: Click and drag to start drawing a structure. : ? g B S olo Ar B Karrow_forward
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