CHAPTER 15. Practice exercises 15.1
|
|
- Zoe Cummings
- 5 years ago
- Views:
Transcription
1 CAPTER 15 Practice exercises (a) C 9 18 : isobutylcyclopentane C : sec-butylcycloheptane C 6 2 : 1-ethyl-1-methylcyclopropane 15.5 (a) 3,3-dimethyl-1-pentene 2,3-dimethyl-2-butene 3,3-dimethyl-1-butyne 15.7 (a) (E)-1-chloro-2,3-dimethyl-2-pentene (Z)-1-bromo-1-chloropropene (E)-2,3,4-trimethyl-3-heptene 15.9 cis,trans-2,4-heptadiene cis,cis-2,4-heptadiene (a) 2-iodopropane
2 1-iodo-1-methylcyclohexane C 3 I C 3 I Step 1: Protonation of the alkene to give the most stable 3 carbocation intermediate: C 3 I slow step rate-determining C 3 I step Step 2: Nucleophilic attack of the iodide anion on the 3 carbocation intermediate to give the product: C 3 I C 3 I O C 3 C 3 3 O O Step 1: Protonation of the alkene to give the most stable 3 carbocation intermediate: slow step C 3 O C 3 rate-determining step O Step 2: Nucleophilic attack of the water on the 3 carbocation intermediate to give the protonated alcohol:
3 C 3 O O C 3 Step 3: The protonated alcohol loses a proton to form the product: O C 3 O C 3 O 3 O (a) 2-phenyl-2-propanol (E)-3,4-diphenyl-3-hexene 3-methylbenzoic acid or m-methylbenzoic acid Review questions 15.1 A hydrocarbon is a compound composed only of hydrogen and carbon atoms In saturated hydrocarbons, each carbon is bonded to four other atoms, either hydrogen or carbon atoms. Unsaturated hydrocarbons have carbon atoms that have a double or triple bond to another carbon atom (a) (d) (e) (f)
4 15.7 (C 2 ) 2 C 3 (a) C 3 (C 2 ) 4 C(C 3 ) 2 C 3 (C 2 ) 2 C(C 2 ) 2 C 3 (C 2 ) 2 C 3 C 3 (C 2 ) 2 C(C 2 ) 4 C 3 C (a) different compounds constitutional isomers constitutional isomers (d) different compounds (e) constitutional isomers (f) constitutional isomers (a) 2-methylpentane 2,5-dimethylhexane 3-ethyloctane (d) 2,2,3-trimethylbutane (e) isobutylcyclopentane (f) 1-tert-butyl-2,4-dimethyl-cyclohexane (a) 1,3-dimethylbutane The longest chain is pentane. The IUPAC name is 2-methylpentane. 4-methylpentane The pentane chain is numbered incorrectly. The IUPAC name is 2-methylpentane. 2,2-diethylbutane The longest chain in pentane. The IUPAC name is 3-ethyl-3-methylpentane. (d) 2-ethyl-3-methylpentane The longest chain is hexane. The IUPAC name is 3,4-dimethylhexane.
5 (e) 2-propylpentane The longest chain is heptane. The IUPAC name is 4-methylheptane. (f) 2,2-diethylheptane The longest chain is octane. The IUPAC name is 3-ethyl-3-methyloctane. (g) 2,2-dimethylcyclopropane The ring is numbered incorrectly. The IUPAC name is 1,1-dimethylcyclopropane. (h) 1-ethyl-5-methylcyclohexane The ring is numbered incorrectly. The IUPAC name is 1-ethyl-3-methylcyclohexane No, because alkanes do not have rings or C C double bonds and so all conformations are usually interconvertable by rotation about a C C single bond. owever, there are some extremely crowded molecules which are locked into specific conformers. These are called conformational isomers or locked conformational isomers and are not correctly defined by cis-trans nomenclature There are two enantiomers of the trans-1,2-dimethylcyclopropane.. C 3 C 2 C 3 cyclopentane methylcyclobutane ethylcyclopropane
6 C 3 C 3 C 3 C 3 C 3 trans-1,2-dimethylcyclopropane 1,1-dimethylcyclopropane C 3 cis-1,2-dimethylcyclopropane (a) trans-2-methylhex-3-ene 2-methyl-3-hex-3-yne 2-methylbut-1-ene (d) 3-ethyl-3-methylpent-1-yne (e) 2,3-dimethylbut-2-ene (f) cis-pent-2-ene (a) 2-isobutylhept-1-ene 1,4,4-trimethylcyclopentene 1,3-cyclopentadiene (d) 3,3-dimethylbut-1-yne (e) 2,4-dimethylpent-2-ene (f) oct-1-yne (g) 2,2,5-dimethylhex-3-yne (h) 3-methylpent-1-yne (a) 2,2-dimethylhex-3-yne oct-2,5-diyne 3,6-dimethylhept-2-ene-4-yne hept-1,4-diyne (a) Correct name: but-2-ene.you must select the longest carbon chain containing the ene functional group but-2-ene 4 Not: 2 3 C methylpropene Correct name: pent-2-ene. You must number the chain to give the first carbon of the double bond the lowest possible number.
7 Not: pent-2-ene pent-3-ene Correct name: 1-methylcyclohexene. By default, the first carbon of the double bond in a ring is given the number 1. In this, case this can also be the ring carbon with the methyl group attached methylcyclohexene Not: 2-methylcyclohexene 2 1 (d) (e) (f) This name is not incorrect even though there is no indication of where the double bond is positioned. The indication of the two methyls on the third carbon means that the double bond is attached to the first carbon. Technically, the correct name is 3,3-dimethylpent-1-ene. Correct name: 4-hexyne. As with the chain carbons are numbered to give the first carbon of the double bond the lowest possible number C 3 C 2 C 2 C CC 2 C Correct name: 2-isopropyl-2-butene. The longest chain containing the function group is a pentene (a) No Yes Yes (d) No (e) Yes (f) No
8 (e) For alkenes to exist as a pair of cis-trans isomers, both carbons of the double bond must have two different substituents. Thus, only and (d) can exist as a cis or trans isomer. 3 C cis-bromoprop-1-ene 3 C trans-bromoprop-1-ene (d) Molecules (a) and do not show cis-trans isomerism. (d) (a) Alkenes that do not show cis-trans isomerism are: pent-1-ene 2-methylbut-2-ene 3-methylbut-1-ene 2-methylbut-1-ene Alkenes that do show cis-trans isomerism are: trans-pent-2-ene cis-pent-2-ene
9 Cycloalkanes that do not show cis-trans isomerism are: C 2 C 3 C3 3 C C 3 cyclopentane methylcyclobutane ethylcyclopropane 1,1-dimethyl cyclopropane (d) Cycloalkanes that do show cis-trans isomerism are: 3 C C 3 3 C C 3 cis-1,2-dimethylcyclopropane trans-1,2-dimethylcyclopropane (a) C CC is more stable. C 3 3 C 3 C C C is more stable C 3 C 3 C=C 2 6O 2 4CO O Ni C C O 2 SO 4 C 3 C 3 C 3 C 2 O 2 C=C 2 C 3 C 2 2 (d) 2 C C 2 C 2 C 2 (e) 2 C C 2 C 3 C 2
10 / Pd/C 2 Lindlar catalyst 2 Na/N (a) 1-bromo-2-chloro-4-ethylbenzene 4-iodo-1,2-dimethylbenzene I 2,4,6-trinitrotoluene (d) 4-phenylpentan-2-ol O 2 N NO 2 O NO 2
11 (e) p-cresol (f) 2,4-dichlorophenol O O (g) 1-phenylcyclopropanol (h) styrene (phenylethene) O (i) m-bromophenol (j) 2,4-dibromoaniline O N 2 (k) isobutylbenzene (l) m-xylene isopropylbenzene
12 (1) /Al 3 (2) / 2 SO 4 (3) O / 2 SO 4 Review problems (1) Alkanes are less dense than water. (2) As alkane molar mass increases, density increases. (3) Constitutional isomers have similar densities Boiling points of unbranched alkanes are related to their surface area: the larger the surface area, the greater the strength of the dispersion forces and the higher the boiling point. The relative increase in molecular size per C 2 group is greatest between C 4 and C 3 C 3 and becomes progressively smaller as molecular mass increases. Therefore, the increase in boiling point per C 2 group is greatest between C 4 and C 3 C 3, and becomes progressively smaller for the higher alkanes (a) No Yes Yes (d) It is a liquid. (e) It is less dense than water The three structures with molecular formula C22 are 1,1-dibromoethane, cis-1,2- dibromoethane and trans-1,2-dibromoethane. The dipole moment of the C bond is shown in the structures below by a solid arrow. trans-1,2-dibromoethane has no dipole moment because the two C dipoles point in opposite directions and therefore cancel each other out. owever, 1,1-dibromoethane and cis-1,2-dibromoethane both have a net dipole moment (in the direction shown by the dotted arrow) since the two C dipoles do not point in opposite directions. C C C C C C No dipole moment 1,1-dibromoethane cis-1,2-dibromoethane trans-1,2-dibromoethane (a)
13 C 3 C 3 C C 3 C C cis-4-methylpent-2-ene C 3 C 3 C C C C 3 trans-4-methylpent-2-ene C 3 C 3 CC 2 C C 2 4-methylpent-1-ene (a) 2,2-dichlorobutane
14 butan-2-ol 2,2,3,3-tetrabromobutane A hydrocarbon of formula C 5 8 must have a triple bond, or two double bonds, or a combination of a double bond and a ring. Since it only reacts with one mole of 2 indicates that the compound is an alkyne. Lindlar s catalyst gives a cis alkene, which in turn is brominated to give a dibromoalkane which has two chiral carbons. Only the final possibility shown below meets this last criterion. OR OR (a) The formation of the more stable tertiary carbocation intermediate proceeds at a faster rate, therefore 2-methylbut-2-ene reacts faster than trans-but-2-ene.
15 I trans-but-2-ene secondary carbocation 2-iodobutane I 2-methylbut-2-ene tertiary carbocation 2-iodo-2-methyl butane (major product) The formation of the more stable tertiary carbocation intermediate proceeds at a faster rate, therefore 1-methylcyclohexene reacts faster than cyclohexene. I cyclohexene secondary carbocation iodocyclohexane C C 3 C 3 3 I 1-methylcyclohexene tertiary carbocation 1-iodo-1-methyl cyclohexane (major product) The first step in the reaction is the protonation of the alkene to generate a carbocation. The reaction path that produces the more stable carbocation occurs at a faster rate, thus producing the observed regioselectivity. (a) C 3 C 3 C CC 2 C 3 I C 3 C 3 CC 2 C 2 C 3 I C 3 2 O C 3 C 3 C CC 2 C 3 C 3 CC 2 C 2 C 3 2 SO 4 O
16 15.69 (a) Chlorine undergoes an anti-addition to alkenes. (a) 2 2 C 3 3 C 2 2 (d) C Both cis- and trans-hex-3-ene yield hexan-3-ol upon acid-catalysed hydration because they both form the same carbocation intermediate that leads to hexan-3-ol according to the partial mechanism: O O O (a) 2 O 3 O O
17 C 3 C 3 2 O 3 O C 3 O C 3 2 O O C 3 3 O C 3 (d) 3 C 2 O 3 O 3 C O Step 1: Protonation of the alkene gives a stable 3 carbocation intermediate: C 3 C 3 C C 2 O C3 3 C C 3 C C 3 O C 3 Step 2: Nucleophilic attack of methanol on the carbocation intermediate yields a protonated ether intermediate. 3 C C 3 C 3 C O C 3 3 C C 3 C O C 3 C 3 Step 3: Proton loss by the protonated ether intermediate yields the ether and regenerates the acid catalyst. 3 C C 3 C O C 3 C 2 C 3 O 3 C C 3 C O C 3 C 3 O C The skeleton and location of the double bonds in hydrocarbon A are identified from the structure of the brominated product:
18 2 mol 2 ydrocarbon A (C 5 8 ) 2-methylbuta-1,3-diene 1,2,3,4-tetrabromo-2-methylbutane (a) 2 2 O 2 SO 4 O ( d ) 2 P t (a) or 2 O 2 SO 4 O 2
19 15.85 Resonance accounts for the three equivalent structures of naphthalene: (a) - 8 π electrons - Non-aromatic - 14 π electrons - Not planar - Non-aromatic O N - 10 π electrons - Planar - Aromatic (d) B (e) O (f) O - 6 π electrons - Planar - Aromatic - 6 π electrons - Not a 2p orbital on every atom - Non-aromatic - 8 π electrons - Non-aromatic Although compound contains 14 π electrons (a ückel number), a closer inspection of the molecule reveals that the protons inside the ring are held too close together and force the ring to be non-planar. Molecular modelling of structure confirms its non-planarity and it therefore non-aromatic. In compound, only one of the electron pairs on oxygen is in a 2p orbital, the other electron pair is in an sp 2 hybridised orbital, perpendicular to the π bonds. The nitrogen lone pair in compound is also in a 2p orbital for a total of 10 π electrons in a planar ring making it aromatic. In compound (d), the boron atom contributes an empty 2p orbital, giving an aromatic compound with six π electrons in a seven-membered ring with seven 2p orbitals. Compound (f), is similar to compound where the oxygen has one electron pair in a 2p orbital and the other in an sp 2 hybridised orbital with a total of eight π electrons, giving a non-aromatic compound Two monochloronaphthalenes are possible when naphthalene is treated with 2 /Al 3 : 2 Al 3
20 15.91 Al 2 3 C 2 2 C 2 Step 1: Formation of Lewis acid-lewis base complex: C 2 Al C 2 Al Step 2: Nucleophilic attack of benzene on the electrophilic Lewis acid-lewis base complex and the formation of a resonance-stabilised carbocation (two more resonance structures exist): C 2 Al C 2 Al 4 - Step 3: Deprotonation of the carbocation to give benzyl chloride,, and Al 3 : C 2 Al C 2 Al 3 Step 4: Formation of Lewis acid-lewis base complex between benzyl chloride and Al 3 : C 2 Al C 2 Al Step 5: Dissociation of the complex to give a resonance-stabilised benzyl cation (only one out of five contributing structures is shown) and Al 4 : C 2 Al C 2 Al
21 Step 6: Nucleophilic attack of the second molecule of benzene on the benzylic cation to form another resonance-stabilised carbocation (only one structure is shown): C C 2 2 Step 7: Deprotonation of the carbocation intermediate to regenerate the aromatic ring (diphenylmethane),, and Al 3 : Al C 2 C 2 Al 3 Additional exercises A molecular model of cyclohexane shows hindered rotation about the C C single bonds, allowing the possibility of cis-trans isomers in disubstituted six-membered rings. The much larger cyclododecane ring is flexible enough to allow unrestricted rotation about the C C single bonds, thus no cis-trans isomerisation exists. C 3 C 3 C 3 C 3 C 3 cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane C 3 1,2-dimethylcyclododecane (a) o 120 o C 2 O 120 o 180 o C C C C 120 o (d) 120 o
22 o O o o (a) 180 o (d) 120 o 120 o o (a) Carbons 1 and 3 are sp 2 hybridised. Carbon 2 is sp hybridised. π 2pz -2p z y-axis z-axis π 2py -2p y Each of the terminal carbons is sp 2 hybridised and thus has three sp 2 orbitals oriented 120 apart. Two of these sp 2 hybrid orbitals form sigma bonds with hydrogen atoms and the third forms a sigma bond with the central carbon. Each terminal carbon has one 2p orbital (C1 has a 2p z orbital and C3 has a 2p y orbital) that each form a π bond with the 2p z and 2p y orbitals on the central carbon atom. Because these two 2p orbitals on the centre carbon atom are at right angles to each other, the 2p orbitals on the terminal carbons must be at right angles to each other to permit full orbital overlap Molecules of the trans isomer can pack together more tightly than those of the cis isomers, which means that the dispersion forces controlling intermolecular bonding are greater for the trans than for the less symmetrical cis isomer. COO COO COO COO COO COO The trans isomer of octadec-9-enoic acid can pack together closely and so it has a higher melting point (44 45 C) than the cis isomer.
23 COO COO COO COO (a) O 2 O 2 enzyme catalyst O 2 2 O heat O O Yes
16.1 Draw Newman projections for these staggered and three eclipsed conformations of 1, 2 - dichlorobutane as viewed downt he central C-C bond.
CAPTER 16 Practice Exercises 16.1 Draw Newman projections for these staggered and three eclipsed conformations of 1, 2 - dichlorobutane as viewed downt he central C-C bond. 16.3 (a) The more stable conformation
More informationCHE1502. Tutorial letter 201/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry CHE1502/201/1/2016
CE1502/201/1/2016 Tutorial letter 201/1/2016 General Chemistry 1B CE1502 Semester 1 Department of Chemistry This tutorial letter contains the answers to the questions in assignment 1. FIRST SEMESTER: KEY
More informationClass XI Chapter 13 Hydrocarbons Chemistry
Question 13.1: How do you account for the formation of ethane during chlorination of methane? Chlorination of methane proceeds via a free radical chain mechanism. The whole reaction takes place in the
More information1. How do you account for the formation of ethane during chlorination of methane?
1. How do you account for the formation of ethane during chlorination of methane? The formation of ethane is due to the side reaction in termination step by the combination of two CH 3 free radicals. 2.
More informationST. JOSEPH S COLLEGE OF ARTS & SCIENCE (AUTONOMOUS) ST. JOSEPH S COLLEGE ROAD, CUDDALORE CH101T ORGANIC CHEMISTRY I (SEMESTER-I)
UNIT I 1. The hybridization involved in the formation of acetylene is a) sp b) sp 2 c) sp 3 d) sp 3 d 2. The IUPAC name of is 1. 3-hexene b) 4-hexene c) 3-hexyne d) 4-hexyne 3. -------- is the type of
More informationChapter 3. Alkenes And Alkynes
Chapter 3 Alkenes And Alkynes Alkenes ydrocarbons containing double bonds C C double bond the functional group center of reactivity Molecular Formula of Alkene Acyclic alkene: C n 2n Cyclic alkene: C n
More informationA. They all have a benzene ring structure in the molecule. B. They all have the same molecular formula. C. They all have carbon and hydrogen only
Ch 21 G12 CoreI- Choose the best answer, then transfer your answers to page (1) [32 marks; 2 each] 1. What characteristic do all aromatic hydrocarbons share? A. They all have a benzene ring structure in
More informationUnit 2, Review for Quiz #1: Hydrocarbons
Unit 2, Review for Quiz #1: Hydrocarbons 1. What is the simplest organic molecule? a) CH 4 c) HCN b) CO 2 d) HC CH 2. Which of the following molecules would be classified as organic? I) CaCO 3 II) C 2
More informationBRCC CHM 102 Class Notes Chapter 11 Page 1 of 9
BRCC CHM 102 Class Notes Chapter 11 Page 1 of 9 Chapter 11 Alkanes and Cycloalkanes hydrocarbons compounds that contain only carbon and hydrogen * 4 families: 1) alkanes only single bonds (includes cycloalkanes)
More informationCHE1502. Tutorial letter 203/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry
E1502/203/1/2016 Tutorial letter 203/1/2016 General hemistry 1B E1502 Semester 1 Department of hemistry This tutorial letter contains the answers to the questions in assignment 3. FIRST SEMESTER: KEY T
More informationUnit 5: Organic Chemistry
Unit 5: Organic Chemistry Organic chemistry: discipline in chemistry focussing strictly on the study of hydrocarbons compounds made up of carbon & hydrogen Organic compounds can contain other elements
More informationFAMILIES of ORGANIC COMPOUNDS
1 SCH4U October 2016 Organic Chemistry Chemistry of compounds that contain carbon (except: CO, CO 2, HCN, CO 3 - ) Carbon is covalently bonded to another carbon, hydrogen and possibly to oxygen, a halogen
More informationUNSATURATED HYDROCARBONS
C20 09/16/2013 15:47:28 Page 295 CHAPTER 20 UNSATURATED HYDROCARBONS SOLUTIONS TO REVIEW QUESTIONS 1. The sigma bond in the double bond of ethene is formed by the overlap of two sp 2 electron orbitals
More informationCHAPTER 12: SATURATED HYDROCARBONS
CHAPTER 12: SATURATED HYDROCARBONS MULTIPLE CHOICE 1. Which of the following statements concerning organic compounds is correct? Organic compounds are found only in non-living systems. b. Organic compounds
More informationOrganic Chemistry. A. Introduction
Organic Chemistry A. Introduction 1. Organic chemistry is defined as the chemistry of CARBON compounds. There are a huge number of organic compounds. This results from the fact that carbon forms chains
More information1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound?
CEM 331: Chapter 1/2: Structures (Atoms, Molecules, Bonding) 1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound? N C 2 C N C 2 C N 1 2 3 4 1: three sigma bonds and
More informationUnsaturated Hydrocarbons
Unsaturated ydrocarbons hemical Formulas and Unsaturation n n 2n n 2n+2 n 2n+2 hemical Formulas and Unsaturation n n n n 2n n 2n hemical Formulas and Unsaturation ydrocarbons Saturated ydrocarbons Unsaturated
More informationChem 1120 Midterm points Dr. Luther Giddings
Chem 1120 Midterm 1 100 points Dr. Luther Giddings Name Instructions: This is a closed book, closed notebook test. You may not discuss this exam with anyone, either during or after the exam, until it has
More informationIUPAC Nomenclature Chem12A, Organic Chemistry I
IUPAC Nomenclature ChemA, rganic Chemistry I IUPAC PEFIXES Prefix Substituent Group Number of Carbons meth- methyl eth- ethyl prop- propyl but- butyl pent- pentyl hex- hexyl hept- heptyl 7 oct- octyl 8
More informationChapter 2: Alkanes MULTIPLE CHOICE
Chapter 2: Alkanes MULTIPLE CHOICE 1. Which of the following orbitals is properly described as an antibonding orbital? a. sp + 1s d. sp 2 1s b. sp 2 + 1s e. sp 2 + sp 2 sp 3 + 1s D DIF: Easy REF: 2.2 2.
More informationUNIT (7) ORGANIC COMPOUNDS: HYDROCARBONS
UNIT (7) RGANI MPUNDS: YDRARBNS rganic chemistry is the study carbon containing compounds. 7.1 Bonding in rganic ompounds rganic compounds are made up of only a few elements and the bonding is almost entirely
More informationUnsaturated hydrocarbons. Chapter 13
Unsaturated hydrocarbons Chapter 13 Unsaturated hydrocarbons Hydrocarbons which contain at least one C-C multiple (double or triple) bond. The multiple bond is a site for chemical reactions in these molecules.
More informationAlkanes 3/27/17. Hydrocarbons: Compounds made of hydrogen and carbon only. Aliphatic (means fat ) - Open chain Aromatic - ring. Alkane Alkene Alkyne
Alkanes EQ 1. How will I define Hydrocarbons? 2. Compare and contrast the 3 types of hydrocarbons (Alkanes, alkenes, alkynes). Hydrocarbons: Compounds made of hydrogen and carbon only. Aliphatic (means
More information1. Multiple Choice Questions (15 points) Please circle the best answer to each question. Lone pairs are generally not shown.
Page 2 Name _ANSWER KEY_ 1. Multiple Choice Questions (15 points) Please circle the best answer to each question. Lone pairs are generally not shown. (i) The formal charges on the nitrogen and oxygen atoms
More informationTest Bank for Organic Chemistry 8th Edition by Wade
Test Bank for Organic Chemistry 8th Edition by Wade Link download full: https://testbankservice.com/download/test-bankfororganic-chemistry-8th-edition-by-wade/ Organic Chemistry 8th Edition Test Bank Wade
More information4. A sample of 0.200g of an organic compound was subjected to combustion analysis and
1. A sample of 0.205g of an organic compound was subjected to combustion analysis and produced 0.660g of carbon dioxide, 0.225g of water and nothing else. Its RMM is 82. 2. A sample of 0.400g of an organic
More informationFull file at
Chapter 2 - Alkanes: The Nature of Organic Compounds 1. Which of the following functional group classifications do not contain oxygen? A. ether B. thiol C. aldehyde D. ester E. amide 2. To which functional
More informationStructure and Preparation of Alkenes: Elimination Reactions
Structure and Preparation of Alkenes: Elimination Reactions Alkene Nomenclature First identify the longest continuous chain that includes the double bond. Replace the -ane ending of the corresponding unbranched
More informationCh09. Alkenes & Alkynes. Unsaturated hydrocarbons. Double and triple bonds in our carbon backbone. version 1.0
Ch09 Alkenes & Alkynes Unsaturated hydrocarbons. Double and triple bonds in our carbon backbone. version 1.0 Nick DeMello, PhD. 2007-2015 Ch09 Alkenes & Alkynes Alkenes & Alkynes Definition and bond angles.
More informationCHEM 2312 practice final. Version - II
EM 2312 practice final Version - II The following standardized final examination covers the entire introductory year of organic chemistry (EM 2311 and 2312 at Georgia Tech). The exam consists of 70 multiple
More informationHYDROCARBON COMPOUNDS
YDROARBON OMPOUNDS hapter Quiz lassify each of these statements as always true, AT; sometimes true, ST; or never true, NT. 1. ydrocarbons are unsaturated. 22.2 2. The IUPA name for 3(2)33 is butane. 22.1
More informationChapter 4 Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis"
Chapter 4 Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis" Alkanes = saturated hydrocarbons" Simplest alkane = methane C 4" " We can build additional alkanes by adding
More informationStudy Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner?
Study Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner? A) They are isotopes B) They are constitutional isomers C) They are the same structure D) They are composed
More informationunsaturated (one or more pi bonds) alkanes alkenes alkynes benzene naming alkanes C 4 H 10 C 5 H 12 C 6 H 14 C 7 H 16 C 8 H 18 C 9 H 20 C 10 H 22
hapter 4: Alkanes and ycloalkanes [Sections: 4.1-4.14] Basic Organic ompound Nomenclature hydrocarbons: comprised of just carbon and hydrogen saturated (no pi bonds) unsaturated (one or more pi bonds)
More information1. What is the letter designation given to dumbbell shaped orbitals like the one depicted below?
1. What is the letter designation given to dumbbell shaped orbitals like the one depicted below? 2. Which of the following does not have an octet of electrons surrounding the central atom? A. B 3 B. C
More informationStudy Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner?
Study Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner? A) They are isotopes B) They are constitutional isomers C) They are the same structure D) They are composed
More informationChemistry 20 Chapters 2 Alkanes
Chemistry 20 Chapters 2 Alkanes ydrocarbons: a large family of organic compounds and they contain only carbon and hydrogen. ydrocarbons are divided into two groups: 1. Saturated hydrocarbon: a hydrocarbon
More informationNational 5 Chemistry. Unit 2 Nature s Chemistry Summary Notes
National 5 Chemistry Unit 2 Nature s Chemistry Summary Notes Success Criteria I am confident that I understand this and I can apply this to problems? I have some understanding but I need to revise this
More informationOrganic Chemistry. A brief introduction
Organic Chemistry A brief introduction Organic Chemistry the study of carbon-containing compounds and their properties excluding: CO, CO 2, CS 2, carbonates and cyanides eight million known organic compounds
More informationChemistry 110. Bettelheim, Brown, Campbell & Farrell. Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes.
Chemistry 110 Bettelheim, Brown, Campbell & Farrell Ninth Edition Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes Chapter 12 Alkenes are hydrocarbons which have one or more
More informationChemistry 110 Bettelheim, Brown, Campbell & Farrell Ninth Edition Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes
Chemistry 110 Bettelheim, Brown, Campbell & Farrell Ninth Edition Introduction to General, Organic and Biochemistry Chapter 12 Alkenes & Alkynes Chapter 12 Alkenes are hydrocarbons which have one or more
More informationChapter 22. Organic and Biological Molecules
Chapter 22 Organic and Biological Molecules The Bonding of Carbon Organic chemistry is the chemistry of compounds containing carbon. Because carbon can form single, double, and triple bonds, the following
More informationGeneral Chemistry Unit 7A ( )
Organic Chemistry Allotropes Isomers Hydrocarbons o Alkanes o Alkenes o Alkynes o Aromatics Alkyl Halides General Chemistry Unit 7A (2017-2018) 1 2 3 4 Parent Chain: Methane Ethane CH4 C2H6 Propane C3H8
More informationDAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 5 Dr Ali El-Agamey 1 Energy Diagram of One-Step Exothermic Reaction The vertical axis in this graph represents the potential energy. The transition
More informationChapter 2: Hydrocarbon Frameworks - Alkanes
Chapter 2: Hydrocarbon Frameworks - Alkanes 1. Alkanes are characterized by the general molecular formula: A) C n H 2n-2 B) C n H 2n C) C n H 2n+2 D) C n H 2n+4 2. Cycloalkanes are characterized by the
More informationSummary Chapter General, Organic, & Biological Chemistry Janice Gorzynski Smith
Summary Chapter 11-12 General, Organic, & Biological Chemistry Janice Gorzynski Smith Organic Chem Review: Valence Electrons Example: Determine the valence electrons of Selenium (Se): 1. Find Se on the
More informationIntroduction to Organic Chemistry. Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Introduction to Organic Chemistry Copyright The McGraw-ill Companies, Inc. Permission required for reproduction or display. 1 Common Elements in Organic Compounds 2 Classification of ydrocarbons ydrocarbons
More informationAlkanes and Cycloalkanes
Alkanes and Cycloalkanes Alkanes molecules consisting of carbons and hydrogens in the following ratio: C n H 2n+2 Therefore, an alkane having 4 carbons would have 2(4) + 2 hydrogens, which equals 10 hydrogens.
More informationORGANIC CHEMISTRY: SATURATED HYDROCARBONS
19 09/16/2013 13:54:37 Page 283 APTER 19 ORGANI EMISTRY: SATURATED YDROARBONS SOLUTIONS TO REVIEW QUESTIONS 1. Two of the major reasons for the large number of organic compounds is the ability of carbon
More informationChapter 3 Alkenes and Alkynes. Excluded sections 3.15&3.16
Chapter 3 Alkenes and Alkynes Excluded sections 3.15&3.16 3.1 Definition and Classification Alkene: a hydrocarbon that contains one or more carboncarbon double bonds. ethylene is the simplest alkene. Alkyne:
More information12.01 Organic Chemistry
12.01 rganic hemistry hemistry of arbon An Introduction to nomenclatures, structures and reactions Dr. Fred mega Garces hemistry 100 Miramar ollege 1 rganic hemistry What is rganic hemistry? rganic hemistry:
More informationI. Multiple Choice Questions (Type-I)
Unit 13 HYDROCARBONS I. Multiple Choice Questions (Type-I) 1. Arrange the following in decreasing order of their boiling points. (A) n butane (B) 2 methylbutane (C) n-pentane (D) 2,2 dimethylpropane A
More informationAlkanes and Cycloalkanes
Alkanes and Cycloalkanes Families of Organic Compounds Organic compounds can be grouped into families by their common structural features We shall survey the nature of the compounds in a tour of the families
More informationAlkanes and Cycloalkanes
Chapter 3 Alkanes and Cycloalkanes Two types Saturated hydrocarbons Unsaturated hydrocarbons 3.1 Alkanes Also referred as aliphatic hydrocarbons General formula: CnH2n+2 (straight chain) and CnH2n (cyclic)
More informationChapter 12: Unsaturated Hydrocarbons
Chapter 12: Unsaturated Hydrocarbons UNSATURATED HYDROCARBONS contain carbon-carbon multiple bonds. Alkenes C=C double bonds Alkynes triple bonds Aromatics benzene rings 1 2 NAMING ALKENES Step 1: Name
More informationChem 145 Unsaturated hydrocarbons Alkynes
Dr. Seham ALTERARY Chem 145 Unsaturated hydrocarbons Alkynes Chapter 4 1434-1435 2013-2014 2 st semester By the end of this chapter you should be familiar with: Definition for Alkynes. Nomenclature of
More informationOrganic Chemistry. FAMILIES of ORGANIC COMPOUNDS
1 SCH4U September 2017 Organic Chemistry Is the chemistry of compounds that contain carbon (except: CO, CO 2, HCN, CO 3 2- ) Carbon is covalently bonded to another carbon, hydrogen and possibly to oxygen,
More information1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound?
EM 331: hapter 1/2: Structures (Atoms, Molecules, Bonding) 1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound? N 2 N 2 N 1 2 3 4 2. What hybrid orbitals are used to
More informationCH 3. mirror plane. CH c d
CAPTER 20 Practice Exercises 20.1 The index of hydrogen deficiency is two. The structural possibilities include two double bonds, a double do 20.3 (a) As this is an alkane, it contains only C and and has
More informationCHEM 261 HOME WORK Lecture Topics: MODULE 1: The Basics: Bonding and Molecular Structure Text Sections (N0 1.9, 9-11) Homework: Chapter 1:
CHEM 261 HOME WORK Lecture Topics: MODULE 1: The Basics: Bonding and Molecular Structure Atomic Structure - Valence Electrons Chemical Bonds: The Octet Rule - Ionic bond - Covalent bond How to write Lewis
More informationChapter 10. BrCH 2 CH 2 CH 2 CCH 2 Br CH 3. CH 3 CCH 2 CH 2 Cl CH 3 CHCH 2 CH 2 CHCH Give IUPAC names for the following alkyl halides:
hapter 10 10.1 Give IUPA names for the following alkyl halides: (a), 3 2 2 2 I 1-iodobutane 3 (b), 3 2 2 l 1-chloro-3-methylbutane (c), 3 2 2 2 2 3 1,5-Dibromo-2,2-dimethylpentane 3 3 2 2 l (d), l 1,3-Dichloro-3-methylbutane
More informationChapter 2 Alkanes and Cycloalkanes: Introduction to Hydrocarbons
Chapter 2 Alkanes and Cycloalkanes: Introduction to ydrocarbons Copyright The McGraw-ill Companies, Inc. Permission required for reproduction or display. 2.1 Classes of ydrocarbons ydrocarbons Aliphatic
More informationClasses of Alkenes. Alkenes and Alkynes. Saturated compounds (alkanes): Have the maximum number of hydrogen atoms attached to each carbon atom.
Alkenes and Alkynes Saturated compounds (alkanes): ave the maximum number of hydrogen atoms attached to each carbon atom. Unsaturated compounds: ave fewer hydrogen atoms attached to the carbon chain than
More informationUnit 7 Part 1 Introduction to Organic Chemistry Nomenclature and Isomerism in Simple Organic Compounds UNIT 7 INTRODUCTION TO ORGANIC CHEMISTRY
Unit 7 Part 1 Introduction to Organic hemistry Nomenclature and Isomerism in Simple Organic ompounds UNIT 7 INTRODUTION TO ORGANI EMISTRY PART 1 NOMENLATURE AND ISOMERISM IN SIMPLE ORGANI MOLEULES ontents
More informationCHEM 241 ALKANES AND CYCLOALKANES CHAP 3 ASSIGN H H
CEM 241 ALKANES AND CYCLOALKANES CAP 3 ASSIGN COMFORMATIONS AND cis-trans STEREOISOMERS 1. trans-1,2-dibromocyclohexane is represented by structure(s): D. II and III E. I and II 2. cis-1,3-dibromocyclohexane
More informationDAV CENTENARY PUBLIC SCHOOL, PASCHIM ENCLAVE, NEW DELHI - 87
HYDROCARBONS 1. Why do alkenes prefer to undergo electrophilic addition reaction while arenes prefer electrophilic substitution reactions? Explain. 2. Alkynes on reduction with sodium in liquid ammonia
More informationChemistry B11 Chapters Alkanes, Alkenes, Alkynes and Benzene
Chapters 10-11 Alkanes, Alkenes, Alkynes and Benzene Organic compounds: organic chemistry is the chemistry of carbon and only a few other elements-chiefly, hydrogen, oxygen, nitrogen, sulfur, halogens,
More information2FAMILIES OF CARBON COMPOUNDS:
P1: PBU/VY P2: PBU/VY Q: PBU/VY T1: PBU Printer: Bind Rite JWL338-02 JWL338-Solomons-v1 April 23, 2010 21:49 2AMILIES ARB MPUDS: UTIAL GRUPS, ITERMLEULAR RES, AD IRARED (IR) SPETRSPY SLUTIS T PRBLEMS 2.1
More informationSummary Chapter 13-14
Summary Chapter 1-1 Nomenclature 1 prefix + + prefix,- dimethyl 1,5- First give locajon and type of subsjtuents Second give locajon of double bond How many carbons in longest chain? How many of the funcjonal
More informationCHEM120 - ORGANIC CHEMISTRY WORKSHEET 1
EM120 - RGANI EMISTRY WRKSEET 1 Some of the objectives To understand and know the hybridization concept Be able to distinguish different geometries, including basic bond lengths and angles within organic
More informationUnit 12 Organic Chemistry
Unit 12 Organic Chemistry Day 138 5/5/14 QOD: What is Organic Chemistry? Do Now: True or false? 1. Electrochemical cells generate electricity. 2. Electrons flow from left to right in a battery. 3. Redox
More informationThis reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds.
This reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds. Mechanism for the addition of a hydrogen halide What happens
More informationChapter 2 Alkanes and Cycloalkanes: Introduction to Hydrocarbons
Chapter 2 Alkanes and Cycloalkanes: Introduction to Hydrocarbons 2.1 Classes of Hydrocarbons Classes of Hydrocarbons Hydrocarbons only contain carbon and hydrogen atoms. Hydrocarbons are either classed
More informationCH 3 CH 2 CH 2 CH 2 CH 2 CH 2 OH
03SEP 18:00 19:00 ORGANIC MOLECULES STUDY NOTES ORGANIC MOLECULES Important features of Carbon Carbon has a valency of 4 (can form 4 bonds), and has 4 valence electrons (outermost energy level). Carbon
More informationChapter 2: An Introduction to Organic Compounds
Chapter : An Introduction to Organic Compounds I. FUNCTIONAL GROUPS: Functional groups with similar structure/reactivity may be "grouped" together. A. Functional Groups With Carbon-Carbon Multiple Bonds.
More informationUnit 9. Organic compounds
Unit 9. Organic compounds Index 1.- How to Name Organic Compounds...2 2.- Types of Compounds...3 Exercises...6 Practice exam...9 Page 1 of 11 The IUPAC Naming (nomenclature) System 1.- How to Name Organic
More informationOrganic Chemistry. February 18, 2014
Organic Chemistry February 18, 2014 What does organic mean? Organic Describes products Grown through natural biological process Without synthetic materials In the 18 th century Produced by a living system
More informationMOLECULER MODELS/ISOMERS ORGANIC STRUCTURES AND NAMING
REVISED 10/14 EMISTRY 1101L MOLEULER MODELS/ISOMERS ORGANI STRUTURES AND NAMING NOTE: This lab does not require safety glasses or lab coats. INTRODUTION Electron Dot Structures: Electron dot structures,
More information3. What number would be used to indicate the double bond position in the IUPAC name for CH 3 CH 2 CH=CH CH 3 a. 1 b. 2 c. 3 d.
Chapter 2 Unsaturated Hydrocarbons MULTIPLE CHOICE 1. Name a difference between a saturated and an unsaturated hydrocarbon. a. Saturated hydrocarbons are composed of only carbon and hydrogen, and unsaturated
More informationIntroduction to Alkenes and Alkynes
Introduction to Alkenes and Alkynes In an alkane, all covalent bonds between carbon were σ (σ bonds are defined as bonds where the electron density is symmetric about the internuclear axis) In an alkene,
More informationQuestion. Chapter 5 Structure and Preparation of Alkenes (C n H 2n ): Elimination Reactions
hapter 5 Structure and Preparation of Alkenes ( n 2n ): Elimination Reactions The molecular formula of β-arotene is 40 On catalytic hydrogenation, β-carotene is converted to a saturated hydrocarbon of
More information1.8. Organic Chemistry. Practice Exam Organic Chem. System LENGTH: VOLUME MASS Temperature. 1 gal = 4 qt. 1 lb = 16 oz.
rganic hemistry Practice Exam rganic hem Name (last) (First) Read all questions before you start. Show all work and explain your answers to receive full credit. Report all numerical answers to the proper
More informationNuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320 I. Isolated, cumulated, and conjugated dienes A diene is any compound with two or C=C's is a diene. Compounds containing more than two
More information1) (100 pts) 5) (20 pts) 3) (35 pts) 4) (25pts. Total (200 pts) More Tutorial at
Name: Perm number: Question 1) (100 pts) 2) (20 pts) 3) (35 pts) 4) (25pts 5) (20 pts) Total (200 pts) Your score 1. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers
More informationChapter 3: Alkanes and Cycloalkanes
Chapter 3: Alkanes and Cycloalkanes 55 Chapter 3: Alkanes and Cycloalkanes Problems 3.1 Do the structural formulas in each pair represent the same compound or constitutional isomers? Constitutional isomers
More informationChapter 25: The Chemistry of Life: Organic and Biological Chemistry
Chemistry: The Central Science Chapter 25: The Chemistry of Life: Organic and Biological Chemistry The study of carbon compounds constitutes a separate branch of chemistry known as organic chemistry The
More informationChapter 2: Hydrocarbon Frameworks Alkanes
1. Alkanes are characterized by the general molecular formula: A) CnH2n-2 B) CnH2n C) CnH2n+2 D) CnH2n+4 2. Cycloalkanes are characterized by the general molecular formula: A) CnH2n-2 B) CnH2n C) CnH2n+2
More informationChapter 4: Alkanes and Cycloalkanes
1. Nomenclature hapter 4: lkanes and ycloalkanes hydrocarbons: comprised of just carbon and hydrogen saturated (no pi bonds) [Sections: 4.1-4.14] unsaturated (one or more pi bonds) alkanes alkenes alkynes
More informationCHAPTER 2. Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules
CHAPTER 2 Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules 2-1 Kinetics and Thermodynamics of Simple Chemical Processes Chemical thermodynamics: Is concerned with the extent that
More informationCHEM 203 Exam 1. Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question.
CHEM 203 Exam 1 Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. 1. Which of the following elements is a large percentage of both the earth's
More informationOrganic Chemistry. Saturated Hydrocarbons: The Alkanes. ethane H C C H CH 3 CH 3
rganic hemistry The classification of chemical compounds in to the general areas of organic and inorganic derives from the use of the "mineral, vegetable and animal" designation by the early workers in
More informationChapter 4 Alkanes and Cycloalkanes.! Structure, Nomenclature and Conformations
hapter 4 Alkanes and ycloalkanes Structure, Nomenclature and onformations arbon Bonding Structural Representation of Simple Alkanes Name Kekule structure ondensed structure Model methane ethane propane
More informationMore Tutorial at
1. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question (50 pts). 1) Which of the following statements about propene, CH3CH CH2, is 1) correct? A) There
More information3. Organic Compounds: Alkanes and Cycloalkanes
3. Organic Compounds: Alkanes and Cycloalkanes Based on McMurry s Organic Chemistry, 6 th edition, Chapter 3 2003 Ronald Kluger Department of Chemistry University of Toronto 1 Families of Organic Compounds!
More informationC C. sp 2. π M.O. atomic. orbitals. carbon 1. σ M.O. molecular. orbitals. H C C rotate D. D H zero overlap of p orbitals: π bond broken!
Alkenes Electrophilic Addition 1 Alkene Structures chemistry of double bond σ BDE ~ 80 kcal/mol π = BDE ~ 65 kcal/mol The p-bond is weaker than the sigma-bond The, electrons in the p-bond are higher in
More informationIntroduction to Organic Chemistry: Hydrocarbons
Introduction to Organic Chemistry: Hydrocarbons Chapter 12 Chapter 12 12.1 Organic Compounds 12.2 Alkanes 12.3 Alkanes with Substituents 12.4 Properties of Alkanes 12.5 Alkenes and Alkynes 12.6 Cis-Trans
More informationOrganic Compounds. Introduction to Organic Chemistry: Hydrocarbons. also contain other nonmetals such as oxygen, nitrogen,
Introduction to Organic Chemistry: Hydrocarbons Chapter 12 12.1 Organic Compounds Identify properties characteristic of organic or inorganic compounds. Chapter 12 12.1 Organic Compounds 12.2 Alkanes 12.3
More informationOrganic Chemistry 17.1
Organic Chemistry 17.1 Introduction to Organic Compounds Naming Alkanes Isomers of Alkanes Naming Cycloalkanes What are Organic Compounds? (1807) The term organic compound originated Meant compounds derived
More informationChapter 13 Conjugated Unsaturated Systems
Chapter 13 Conjugated Unsaturated Systems Introduction Conjugated unsaturated systems have a p orbital on a carbon adjacent to a double bond The p orbital can come from another double or triple bond The
More informationDetailed Course Content
Detailed Course Content Chapter 1: Carbon Compounds and Chemical Bonds The Structural Theory of Organic Chemistry 4 Chemical Bonds: The Octet Rule 6 Lewis Structures 8 Formal Charge 11 Resonance 14 Quantum
More information