Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 4, Problem 3LGP
When 1,2-dimethylcyclohexene is allowed to react with hydrogen in the presence of a platinum catalyst, the product of the reaction is a cycloalkane that has a melting point of –50 °C and a boiling point of 130 °C (at 760 torr).
(a) What is the structure of the produce of this reaction?
(b) Consult an appropriate resource (such as the web or a CRC handbook) and tell which stereoisomer it is.
(c) What does this experiment suggest about the mode of addition of hydrogen to the double bond?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Compounds 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.
2,3-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-ene
(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?
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Plants use the process of photosynthesis to convert the energy in sunlight to chemical energy in the form of su...
Campbell Essential Biology (7th Edition)
22. How are stromal and parenchymal repair of a tissue different?
Principles of Anatomy and Physiology
25. The speed of sound in room temperature (20°C) air is 343 m/s; in room temperature helium, it is 1010 m/s. T...
College Physics: A Strategic Approach (3rd Edition)
68. Correct any incorrect equations. If no reaction occurs, write NO REACTION.
a.
b.
c.
d.
Introductory Chemistry (6th Edition)
What were the major microbiological interests of Martinus Beijerinck and Sergei Winogradsky? It can be said tha...
Brock Biology of Microorganisms (15th Edition)
Ice cubes can disappear and food can dry out (freezer burn) in the freezer. That happens to the ice?
Fundamentals Of Thermodynamics
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The melting points and boiling points of two isomeric alkanes are as follows: CH3(CH2)6CH3, mp = -57 °C and bp = 126 °C; (CH3)3CC(CH3)3, mp = 102 °C and bp = 106 °C. (a) Explain why one isomer has a lower melting point but higher boiling point. (b) Explain why there is a small difference in the boiling points of the two compounds, but a huge difference in their melting points.arrow_forward(a) What structural feature is associated with each type of hy-drocarbon: an alkane; a cycloalkane; an alkene; an alkyne? (b) Give the general formula for each type .(c) Which hydrocarbons are considered saturated?arrow_forwardWhich of the following alkenes can exist as cis-trans isomers? Write their structures. (a) CH2=CHCH2CH3 (c) CH2=C(CH3)2 (b) CH3CH=CHCH3 (d) CH3CH2CH=CHCIarrow_forward
- (d) This structure is that of an alcohol with the hydroxyl group on the third C atom of a five-carbon chain.The compound is called pentan-3-olarrow_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_forwardWrite 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
- a) Draw structures for the following compounds. (i) (ii) (iii) 3-ethyl-4-methylhexane 4-tert-butyl-2-methylheptane 3-methylpent-1-ene (b) Provide the IUPAC names for the following (i) (ii) (CH3)3C(CH2)3CH(CH₂CH3)CH₂CH₂CH3arrow_forward(a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?arrow_forwardPropose a structural formula for the product(s) when each of the following alkenes is treated with H2O/H,SO4. Why are two products formed in part (b), but only one in parts (a) and (c)? (a) 1-Hexene gives one alcohol with a molecular for- mula of C,H140. (b) 2-Hexene gives two alcohols, each with a molecu- lar formula of C,H140. (c) 3-Hexene gives one alcohol with a molecular for- mula of C6H140.arrow_forward
- The dehydrogenation of butane to trans-but-2-ene has ∆H ° = +116 kJ>mol (+27.6 kcal>mol) and ∆S° = +117 J>kelvin@mol (+28.0 cal>kelvin@mol).(a) Compute the value of ∆G° for dehydrogenation at room temperature (25 °C or 298 °K).Is dehydrogenation favored or disfavored?arrow_forwardTRUE OR FALSE (a) Both ethylene and acetylene are planar molecules. (b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism. (c) Cis-trans isomers have the same molecular formula but a different connectivity of their atoms. (d) Cis-2-butene and trans -2-butene can be interconverted by rotation about the carbon–carbon double bond. (e) Cis-trans isomerism is possible only among appropriately substituted alkenes. (f) Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers. (g) Cyclohexene can exist as a pair of cis-trans isomers. (h) 1-Chloropropene can exist as a pair of cis-trans isomers.arrow_forwardGive the IUPAC name of the following compounds: (a) HạC CH3 (D) CH3 H2C=CHCHCH3 CH3CH,CH=CCH,CH3 CH3 (c) CH3 (d) CH3CHCH,CH3 CH,CH=CHCHCH=CHCHCH, CH,CH,CH,CH=CHCHCH,CH,arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License