ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Chapter 7, Problem 7PP
Interpretation Introduction
Interpretation:
The formation of
Concept introduction:
The stability of alkene is depending on the number of alkyl group attached to the carbon atom of the double bond.
The stability of alkene increases as the number of alkyl group attached to the carbon atom of double bond increases.
According to the Zaitsev’s rule, in the presence of small base like hydroxide or ethoxide the more highly substituted alkene will be the major product.
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11:43
Q1.
(a)
(c)
(d)
(b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with
ethanolic potassium hydroxide.
(i) Explain what is meant by the term stereoisomers.
Library
Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with
ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂
Name of mechanism
Mechanism
(ii)
Draw the structures and give the names of the two stereoisomers of
but-2-ene.
Stereoisomer 1
Name
(iii) Name this type of stereoisomerism.
Select
Name
Stereoisomer 2
When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide,
2-methylpropan-2-ol is formed as shown by the following equation.
CH3
H₂C-C-CH3 + KOH
Br
Page 2 of 14
CH3
H3C-C-CH3 + KBr
ОН
State the role of the hydroxide ions in this reaction.
Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with
an excess of ammonia. Name the organic product of this reaction.
Equation
Name of product
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For You…
Practice Problem 7.16
When the compound called isoborneol is heated with 9 M sulfuric acid, the product of the reaction is the compound
called camphene and not bornylene, as one might expect. Using models to assist you, write a step-by-step mechanism
showing how camphene is formed.
HO
H,O
not
heat
Isoborneol
Camphene
Bornylene
Can you help me with question (C)
Chapter 7 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
Ch. 7 - Prob. 1PPCh. 7 - Prob. 2PPCh. 7 - Prob. 3PPCh. 7 - Prob. 4PPCh. 7 - Practice Problem 7.5
How many stereoisomers are...Ch. 7 - Prob. 6PPCh. 7 - Prob. 7PPCh. 7 - PRACTICE PROBLEM 7.8
Examine Solved Problem 7.3....Ch. 7 - Prob. 9PPCh. 7 - Practice Problem 7.10 When...
Ch. 7 - Practice Problem 7.11
(a) When...Ch. 7 - Prob. 12PPCh. 7 - Prob. 13PPCh. 7 - Practice Problem 7.14
Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15
Rank the following alcohols...Ch. 7 - Practice Problem 7.16
Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 18PPCh. 7 - Prob. 19PPCh. 7 - Practice Problem 7.20
Show how you might...Ch. 7 - Prob. 21PPCh. 7 - Prob. 22PPCh. 7 - Practice Problem 7.23
Write the structure of...Ch. 7 - Prob. 24PPCh. 7 - Prob. 25PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.36. Explain the following observations: When...Ch. 7 - Prob. 37PCh. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 39PPCh. 7 - Prob. 40PPCh. 7 - Prob. 41PPCh. 7 - Prob. 42PPCh. 7 - Your task is to prepare isopropyl methyl ether by...Ch. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Prob. 48PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 53PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - cis-4-Bromocyclohexanol tBuOHtBuO racemic C6H10O...Ch. 7 - Prob. 59PPCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 61PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGP
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- Draw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forward2. (a) Reaction of an alkene with ozone followed by an oxidative workup gives the product shown. What is the structure of alkene A? A (b) Compounds B and C both have the formula C10H16. Hydrogenation of either compound over Pt gives the same product, cis-1-isopropyl-4-methylcyclohexane. Ozonolysis with reductive workup fragments the two compounds differently, as shown below. What are the structures of C B and C? (CHCl3, chloroform, is the solvent.) B 1) 03, CHCI 3 2) (CH3)2S 1) 03, CHC13 2) (CH3)2S H O 1) 03 2) H₂O2, H₂O H3C- H O CH3 3. (a) Draw the structures of all enols that would spontaneously form this ketone, including stereoisomers. + + I HO₂C H + La CH3CH₂-C-CH(CH3)2 O= (b) Would alkyne hydration be a good preparative method for this compound? If so, give the reaction. If not, explain why.arrow_forward(c) A series of dialkyl ethers react with excess hydrogen bromide, with the following results. Analyze the ether in each case and write out the complete chemical equations. (1) Ether gives a mixture of bromocyclopentane and 1-bromoethane. (ii) Another ether gives one mole of 1,5-dibromopentane per mole of ether.arrow_forward
- • PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forward8.23 In each of the following indicate which reaction will occur faster. Explain your reasoning. (D) Solvolysis of 1-bromo-2,2-dimethylpropane or tert-butyl bromide in ethanol (E) Solvolysis of isobutyl bromide or sec-butyl bromide in aqueous formic acid (F) Reaction of 1-chlorobutane with sodium acetate in acetic acid or with sodium methoxide in methanolarrow_forward7. (1) What would you expect to be the order of reactivity from the following pyridine Derivatives towards electrophilic substitution (i.e. list from most reactive to the least reactive) and why? (ii) Can you also indicate which position would be favoured for such substitution in each of those and why? O,N `NO2arrow_forward
- a) Give the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the following statements:arrow_forwardWrite the structure of the major organic product formed in the reaction of each of the following with hydrogen bromide in the absence of peroxides and in their presence. (a) 1-Pentene (b) 2-Methyl-2-butene (c) 1-Methylcyclohexenearrow_forwardProvide concise syntheses for each of the following compounds starting from but-1 - ene. The source of all the carbon atoms in these molecules must be either but-1 - ene or any one carbon nucleophile/electrophile. (If you must use a reagent that has more than one carbon atoms you must show the preparation of that reagent from but-1 - ene.) (a) Methyl propanoate (b) 3, 5- Dimethylheptan-4-one (c) 5-ethyl-7-methylnon-4-enearrow_forward
- Give explanation of the correct option and explanation of the incorrect options.arrow_forward(2) (1) CH3 -CH2 CH3 This ether can, in principle, be synthesized by two different combinations of haloalkane and metal alkoxide. Draw the combination of alkyl chloride and potassium alkoxide that forms the higher yield of ether.arrow_forward7.44 Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination. (а) СH;CH—CH, (b) (CH3)2С—СH2 (c) BRCH=CB12 CH3 (d) CH3arrow_forward
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