Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 13, Problem 33P
Treating either 1-chloro-3-methyl-2-butene or 3-chloro-3-methyl-1-butene with
(a) Write a mechanism that accounts for the formation of these products.
(b) What might explain the relative proportions of the two
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(b) (1-chloromethyl)cyclopentane, CeH11CI reacts with aqueous sodium
hydroxide, NaOH to produce a primary alcohol AA. When CeH11Cl is added
with magnesium, Mg in ether, an organometallic compound BB is formed.
When compound BB reacts with ethanal, CH3CHO, a secondary alcohol
cCis formed. The molecular structure of CeH11Cl is given below.
(1-klorometil)siklopentana, CoH1,CI bertindak balas dengan akues natrium
hidroksida, NaOH bagi menghasilkan satu alkohol primer AA. Apabila
CeH11CI ditambah dengan magnesium, Mg dalam eter, sebatian
organologam BB terbentuk. Apabila sebatian BB bertindak balas dengan
etanal, CH;CHO, satu alkohol sekunder CC dihasilkan. Struktur molekul
bagi CsH11CI diberikan di bawah.
.CI
(1-chloromethyl)cyclopentane
(i)
Draw the structural formula for compound AA through Cc.
Lukiskan formula struktur bagi sebatian AA sehingga C.
(ii) What is the type of reaction to produce compound AA?
Apakah jenis tindak balas untuk menghasilkan sebatian AA?
Write the reagent or draw structures of the starting material or organic product(s) in
the following reactions. If more than one product is formed, identify the major product
where possible.
(a)
(b)
HO
OH
OH
H2SO4
?
Cl₂
?
FeCl3
Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product).
(a) 3-Hexanol
(b) 1-Methylcyclobutanol
(c) 2-Methyl-2-butanol
(d) 2-Propanol
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGP
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- (b) 3-methyl-2-butanol reacts with concentrated sulphuric acid to form 2-methyl-2- butene. Write the mechanism for the reaction.arrow_forward(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case? (2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.arrow_forwardGive the structure of the product formed when each of the following alkenes reacts with bromine in water: (a) 2-Methyl-1-butene (c) 3-Methyl-1-butene (b) 2-Methyl-2-butene (d) 1-Methylcyclopentenearrow_forward
- (1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?arrow_forward2,3-Dibromoprop-1-ene (C3H4Br2) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule with the formula C3H3Br,Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br,CI; (b) enantiomers of C3H3Br,Cl; (c) diastereomers of C3H3Br,Cl. H нн H Br Br 2,3-Dibromoprop-1-enearrow_forwardPhotochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forward
- Write the bond line formula of the following compounds: (a) 4-methyl-2-hexene, two geometrical (stereoisomers) isomers (b) 3-fluoro-2-methylheptanol (3-fluoro-2-methylheptan-1-ol) (c) 4-methyl-hex-1-yn-3-olarrow_forward(b) (1-chloromethyl)cyclopentane, C6H11CI reacts with aqueous sodium hydroxide, NaOH to produce a primary alcohol AA. When CsH11Cl is added with magnesium, Mg in ether, an organometallic compound BB is formed. When compound BB reacts with ethanal, CH3CHO, a secondary alcohol cC is formed. The molecular structure of C6H11CI is given below. (1-klorometil)siklopentana, C6H11CI bertindak balas dengan akues natrium hidroksida, NaOH bagi menghasilkan satu alkohol primer AA. Apabila C6H11CI ditambah dengan magnesium, Mg dalam eter, sebatian organologam BB terbentuk. Apabila sebatian BB bertindak balas dengan etanal, CH3CHO, satu alkohol sekunder CC dihasilkan. Struktur molekul bagi C6H11CI diberikan di bawah. (1-chloromethyl)cyclopentanearrow_forwardCompounds B and C are hydrocarbons with the structural formulae as shown below. CH, „CH, в (a) Name compounds B and C according to the IUPAC nomenclature. (b) Both B and C can undergo oxidation reaction with the same oxidizing agent. Write chemical equations involved and explain the differences between these two reactions. (c) Name one reaction that converts B to methylcyclohexane.arrow_forward
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