Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 89P
Using the data obtained in Problem 85, calculate the amount of steric in each of the chair conformers 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?
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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 3 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structure of a compound with molecular...Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Prob. 6PCh. 3.1 - Draw the structure for each of the following: a....Ch. 3.1 - Name the following compounds: a. CH3OCH2CH3 b....Ch. 3.2 - Prob. 9PCh. 3.2 - Draw the structure for each of the following: a....Ch. 3.2 - Give each substituent on the nine-carbon chain a...Ch. 3.2 - Prob. 14P
Ch. 3.3 - What is each compounds systematic name?Ch. 3.3 - Prob. 16PCh. 3.3 - Prob. 17PCh. 3.3 - Prob. 18PCh. 3.3 - Prob. 19PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 21PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Prob. 25PCh. 3.6 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Draw condensed and skeletal structures for each of...Ch. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 32PCh. 3.9 - Prob. 33PCh. 3.9 - Prob. 34PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.10 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - Prob. 38PCh. 3.10 - Prob. 39PCh. 3.11 - a. Draw all the staggered and eclipsed conformers...Ch. 3.11 - Prob. 41PCh. 3.11 - Using Newman projections, draw the most stable...Ch. 3.12 - The bond angles in a regular polygon with n sides...Ch. 3.12 - Prob. 44PCh. 3.13 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.14 - Using the data in Table 3.9, calculate the...Ch. 3.14 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.15 - Prob. 48PCh. 3.15 - Which has a higher percentage of the...Ch. 3.15 - a. Draw the more stable chair conformer of...Ch. 3.15 - For each of the following disubstituted...Ch. 3.15 - a. Draw Newman projections of the two conformers...Ch. 3.15 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 56PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 66PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 69PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 72PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - What is each compound s systematic name?Ch. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 88PCh. 3 - Using the data obtained in Problem 85, calculate...Ch. 3 - Draw the conformers for the following...
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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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