Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 3.2, Problem 5P
Propose structures that meet the following descriptions:
(a) Two isomeric esters with the formula C5H10O2
(b) Two isomeric nitriles with the formula C4H7N
(c) Two isomeric disulfides with the formula C4H10S2
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Arrange the following compounds in increasing order of their property as indicated :(i) CH3COCH3, C6H5COCH3, CH3CHO(reactivity towards nucleophilic addition reaction)(ii) Cl—CH2—COOH, F—CH2—COOH, CH3—COOH (acidic character)
(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?
Propose structures for amines that fit these descriptions:(a) A secondary amine with formula C5H13N(b) A tertiary amine with formula C6H13N(c) A cyclic quaternary amine that has the formula C6H14N+
Chapter 3 Solutions
Organic Chemistry
Ch. 3.1 - Prob. 1PCh. 3.1 - Prob. 2PCh. 3.1 - Identify the functional groups in the following...Ch. 3.2 - Draw structures of the five isomers of C6H14.Ch. 3.2 - Propose structures that meet the following...Ch. 3.2 - Prob. 6PCh. 3.3 - Draw the eight 5-carbon alkyl groups (pentyl...Ch. 3.3 - Identify the carbon atoms in the following...Ch. 3.3 - Prob. 9PCh. 3.3 - Prob. 10P
Ch. 3.4 - Give IUPAC names for the following compounds:Ch. 3.4 - Prob. 12PCh. 3.4 - Name the eight 5-carbon alkyl groups you drew in...Ch. 3.4 - Give the IUPAC name for the following hydrocarbon,...Ch. 3.7 - Make a graph of potential energy versus angle of...Ch. 3.7 - Sight along the C2-C1 bond of 2-methylpropane...Ch. 3.7 - Sight along the C2-C3 bond of 2,3-dimethylbutane,...Ch. 3.7 - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 19VCCh. 3.SE - Prob. 20VCCh. 3.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 22APCh. 3.SE - Prob. 23APCh. 3.SE - Propose structures for the following: (a) A...Ch. 3.SE - Prob. 25APCh. 3.SE - Draw the structures of the following molecules:...Ch. 3.SE - Draw structures that meet the following...Ch. 3.SE - Prob. 28APCh. 3.SE - In each of the following sets, which structures...Ch. 3.SE - There are seven constitutional isomers with the...Ch. 3.SE - Prob. 31APCh. 3.SE - Draw compounds that contain the following: (a) A...Ch. 3.SE - Prob. 33APCh. 3.SE - Draw and name all monochloro derivatives of...Ch. 3.SE - Draw structures for the following: (a)...Ch. 3.SE - Prob. 36APCh. 3.SE - Draw a compound that: (a) Has nine primary...Ch. 3.SE - Give IUPAC names for the following compounds:Ch. 3.SE - Name the five isomers of C6H14.Ch. 3.SE - Explain why each of the following names is...Ch. 3.SE - Prob. 41APCh. 3.SE - Consider 2-methylbutane (isopentane). Sighting...Ch. 3.SE - What are the relative energies of the three...Ch. 3.SE - Construct a qualitative potential-energy diagram...Ch. 3.SE - Prob. 45APCh. 3.SE - Draw the most stable conformation of pentane,...Ch. 3.SE - Draw the most stable conformation of...Ch. 3.SE - Prob. 48APCh. 3.SE - Prob. 49APCh. 3.SE - Formaldehyde, H2C=O, is known to all biologists...Ch. 3.SE - Prob. 51APCh. 3.SE - Increased substitution around a bond leads to...Ch. 3.SE - Prob. 53APCh. 3.SE - In the next chapter we'll look at...Ch. 3.SE - We’ll see in the next chapter that there are two...
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- (a) Draw the structure of the following :(i) p-Methylbenzaldehyde (ii) 4-Methylpent-3-en-2-one(b) Give chemical tests to distinguish between the following pairs of compounds :(i) Benzoic acid and Ethyl benzoate, (ii) Benzaldehyde and Acetophenone.(iii) Phenol and Benzoic acid.arrow_forwardDraw the structures of the following compounds:(a) Ethanoic acid(b) Bromopentane(c) Butanonearrow_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_forward
- and (ii) KMnO4 in aqueous NaOH: 1. Name the following alkenes, and predict the products of their reaction with (i) KMnO4 in aqueous acid (a) (b) 2. Draw structures corresponding to the following IUPAC names: (a) 3-Ethylhept-1-yne (b) 3,5-Dimethylhex-4-en-1-yne (c) Hepta-1,5-diyne (d) 1-Methylcyclopenta-1,3-diene (1) 3. Draw and name all the possible pentyne isomers, C5H8. H H Ç-H [ Pent-1-yne] (2) 4. Predict the products of the following ring is inert to all the indicated reagents.) 4 H 4- (3) 4-C C = C-4 [3-methylbut -1-4 [Pent-2-yhdioselectivity where relevant. (The aromatic CH=CH2 Styrene (a) Styrene+H2 Pd, ? (c) Styrene+HBr ? (b) Styrene+Br2 → ? (d) Styrene+KMnO4 NaOH, H2O ? 5. Suggest structures for alkenes that give the following reaction products. There may be more than one answer for some cases. HyPd catalyst (a) ? Br₂ in CH2Cl2 (b) ? HBr (c) ? 2-Methylhexane 2,3-Dibromo-5-methylhexane 2-Bromo-3-methylheptane CH3 HO OH CH3CHCH2CHCHCH2CH3 KMnO4OH (d) ? H₂Oarrow_forwardDraw structural formulas for the following the compounds: (a) Cis-1,3-diphenylcyclohexane (b) 5-phenylpentanoic acid (c) 3,4-dibromo-N,N-dimethylanilinearrow_forwardWrite 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 ? FeCl3arrow_forward
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