Lecture 9 Organic Chemistry 1
|
|
- Shannon Daniel
- 6 years ago
- Views:
Transcription
1 EM 232 Organic hemistry I at hicago Lecture 9 Organic hemistry 1 Prof. Duncan J. Wardrop 02/09/2010 1
2 Functional Group larification Although they can be viewed as ethers, epoxides are classified as distinct, three-atom functional groups... O O Ether Epoxide q. Why? a. Epoxides display distinctly different reactivity to ethers, which arises from their considerable ring strain. University of Illinois at hicago EM 232, Spring 2010 Slide 2 Lecture 5: January 26 2
3 Defining Regioselectivity Regioselectivity (regioselective) A regioselective reaction is one in which one direction of bond making or breaking occurs preferentially over all other possible directions. Reactions are termed completely (100%) regioselective if the discrimination is complete, or partially (<100%), if the product of reaction at one site predominates over the product of reaction at other sites. The discrimination may also semi-quantitatively be referred to as high or low regioselectivity. IUPA ompendium of hemical Terminology 2nd Edition (1997) O Br N O l 4, hν l l l Regioselective hlorination......not stereoselective! at hicago EM 232, Spring 2010 Slide 3 3
4 Mechanism of Alkane hlorination Initiation l l homolysis light (hν) l + 7 valence electrons l Propagation l l l hydrogen abstraction ~1,000,000 cycles per initiation step halogen abstraction l 7 valence electrons l l at hicago EM 232, Spring 2010 Slide 4 Note that typically, this type of chain reaction can continue for 1,000,000 steps for each initiation event. 4
5 Useful Bond Dissociation Energies: - (1 ; 423 kj/mol); - (2 ; 410 kj/mol); - (3 ; 397 kj/ mol); -l (431 kj/mol); -Br (366 kj/mol); Br-Br (192 kj/mol) Factors Governing Regioselectivity l 2 hν l + l 45% 55% Strength of - Bond Broken l 2 hν l + l Number & Type of Substrate - Bonds Br 2 63% Br 37% + Br Strength of -X Bond Formed and X-X Bond Broken hν >99% <1% at hicago EM 232, Spring 2010 Slide 5 Remember that regioselectivity is only an issue in those substrates that more than one type of - bond. yclohexane, for example, undergoes monochlorination to yield on cyclohexyl chloride. 5
6 Bromination is More Selective Than hlorination l Br chlorination bromination = early transition state structures = late transition state structures Relative Rates (k rel ) of alogenation R 3 (tertiary, 3º) R 2 2 (secondary, 2º) Ea (chlorination) Ea (bromination) Ea (bromination) > Ea (chlorination) Bromination is more selective. R 3 (primary, 1º) ammond Postulate chlorine radicals are higher in energy than bromine radicals = transition states in chlorination are earlier = look more like reactants = less difference in TS energy = less selective = greater mixture bromine radicals are lower in energy than chlorine radicals = transition states in bromination are later = look more like products (radical interm.) = greater difference in TS energy = more selective = less of a mixture at hicago EM 232, Spring 2010 Slide 6 6
7 Quantifying Selectivity of alogenation Relative Rates (krel) of alogenation R3 R22 (tertiary, 3º) (secondary, 2º) chlorination bromination Predicted Product Ratios R3 (primary, 1º) Product Relative Yield Absolute Yield % = (krel) x (statistical factor) total chlorination A (2 2º s) 2 x 3.9 = /13.8 = 57% B (6 1º s) 6 x 1 = /13.8 = 43% Sum % l l l A: 57% B: 43% bromination A (2 2º s) 2 x 82 = /170 = 96% B (6 1º s) 6 x 1 = /170 = 4% Sum % Br Br Br A: 96% B: 4% at hicago EM 232, Spring 2010 Slide 7 7
8 Self Test Question Determine the predicted product distribution for A in the following chlorination. Br 2 Br A + Br Relative Rates (k rel ) of alogenation R 3 R 2 2 R 3 (tertiary, 3º) (secondary, 2º) (primary, 1º) chlorination bromination B A. >99% B. 97%. 95% D. 93% E. 91% at hicago EM 232, Spring 2010 Slide 8 Relative Rates for 3 and 1 positions = 1640 and 9, respectively. Absolute yields = 99.4% and 0.6%. The Answer is A. 8
9 EM 232 Organic hemistry I at hicago hapter 5 Nomenclature & Stereoisomerism in Alkenes Section
10 The Terms Alkene and Olefin are Synonymous ethylene 2 4 Alkenes are hydrocarbons that are characterized by a - double bond Also called olefins General molecular formula = n2n Described as unsaturated since they have two fewer atoms than equivalent alkanes at hicago EM 232, Spring 2010 Slide 10 10
11 Index of ydrogen Deficiency (ID) ID is synonymous with degrees of unsaturation and indicates the number of double/triple bonds and/or rings in a molecule ID = 1 (1 double bond) ID = 4 (3 double bonds & 1 ring) ID = 2 (2 rings) ID = 1 (one ring) at hicago EM 232, Spring 2010 Slide 11 11
12 alculating ID 1. ydrocarbons ( n x ) and Oxygenates ( n x O y ): Ignore O (2n+2) - X ID = 2 2. ompounds with N ( n x N y ): Subtract # N from # ID = (2n+2) - (X-Y) 2 3. alogens ( n x X y ): Add # alogens to # ID = (2n+2) - (X+Y) 2 at hicago EM 232, Spring 2010 Slide 12 12
13 ID & The hemistry of Margarine Employing equation 1 (slide 12)... O O linolenic acid m.p. -11 O linoleic acid m.p. -5 O oleic acid m.p. 16 O stearic acid m.p O2 ID = 4 2 / Ni O 1832O2 ID = 3 2 / Ni O 1834O2 ID = 2 2 / Ni O 1836O2 ID = 1 at hicago EM 232, Spring 2010 Slide 13 13
14 IUPA Naming of Alkenes chloro-1-pentene or 4-chloropent-1-ene Steps: 1. Number longest chain that includes both alkene carbons so that they have the lowest locants. 2. Replace -ane ending of parent alkane with -ene (alkene). 3. In the name, list the locant of only the first alkene carbon. onventions/rules: l alkenes have higher priority over alkane and halide substituents when numbering the longest chain alcohols have higher priority over alkenes when numbering the longest chain locant may be placed in front of parent name (e.g. 2-pentene) or in front of suffix (e.g. pent-2-ene). l locant substituent 1st alphabetically parent base alkene locant ene University of Illinois at hicago EM 232, Spring 2010 Slide 14 Lecture 8: February 4 14
15 IUPA Naming of Alkenols hexen-2-ol or hex-4-en-2-ol Steps: 1. Number longest chain that contains both the alkene and the alcohol and so that the alcohol group has lowest locant value. 2. Replace -ane ending of parent alkane with -ene (alkene). 3. In the name, list the locant of only the first alkene carbon. onventions/rules: alkenes have higher priority over alkane and halide substituents when numbering the longest chain alcohols have higher priority over alkenes when numbering the longest chain locant may be placed in front of parent name (e.g. 2-pentene) or in front of suffix (e.g. pent-2-ene). when ene does not occur at the end of a name, drop the last e parent base O 1 alkene locant en O O locant ol University of Illinois at hicago EM 232, Spring 2010 Slide 15 Lecture 8: February 4 15
16 IUPA Functional Group Priorities for Numbering Longest hains Priority Functional Group Suffix Substituent Name Increasing Priority 3 halide n.a. halo 3 alkane -ane alkyl 2 alkene -ene -en (or alkenyl) 1 alcohol (-O) -ol hydroxy We will add to this table as we encounter more functional groups in IUPA nomenclature. at hicago EM 232, Spring 2010 Slide 16 16
17 ommon Alkenyl Group Names Vinylic -atoms R R Methylene R R R Vinyl R Allylic -atoms R Allyl R R Propenyl R at hicago EM 232, Spring 2010 Slide 17 17
18 Alkene Structure & Bonding carbons in an alkenes are sp 2 hybridized bond angles are ~120º around sp 2 hybridized carbons geometry around sp 2 -carbons is planar (flat) 110 pm pm at hicago EM 232, Spring 2010 Slide 18 18
19 Double Bond = 1 π-bond + 1 σ-bond A double bond is formed by two orbital overlaps 1 pi (π) bond side-to-side overlap of two p-orbitals; 2 π-electrons 1 sigma (σ) bond head-to-head overlap of two sp 2 -orbitals at hicago EM 232, Spring 2010 Slide 19 19
20 Bond Rotation of Alkanes vs. Alkenes relative E 3 3 anti-butane 3 3 E a Rotational Barrier = kjmol -1 (rotation about single - bond) 3 3 relative E E a trans-butene Rotational Barrier = 260 kjmol -1 (rotation involves breaking = bond) 3 3 cis-butene at hicago EM 232, Spring 2010 Slide 20 Note that while rotation around = bonds is restricted, rotation about the - and - single bonds is not. 20
21 Alkenes Resist Rotation Round = Bond 90º rotation π-bond prevents full rotation around double bond 90º rotation would break π-bond to generate diradical substituents on alkene locked in spacial relationships some rotation is possible through pyramidalization (more on this topic later) at hicago EM 232, Spring 2010 Slide 21 21
22 Photolysis Mediates = Bond Rotation light (hν) diradical has - single bond mixture of cis and trans π* antibonding M.O. light (hν) promotion of electron to antibonding orbital cancels out = bond π bonding M.O. at hicago EM 232, Spring 2010 Slide 22 22
23 Geometrical Stereoisomers of Alkenes Butene 2-Methylbutene cis-2-butene trans-2-butene Identical 2 3 No possible stereoisomers 3 3 Identical 1-Butene 2-Methylbutene restricted rotation around double bond gives cis and trans geometrical isomers (stereoisomers) cis and trans: relationship between two vicinal groups on alkene cis: same side; trans: opposite sides at hicago EM 232, Spring 2010 Slide 23 23
24 onstitutional vs. onfigurational Isomers isomers constitutional (structural) trans (E) cis (Z) Do the molecules have the same connectivity? no yes stereoisomers an the molecules be interconverted by rotation around single bonds? yes no conformational configurational at hicago EM 232, Spring 2010 Slide 24 24
25 Stereoisomers stereoisomers an the molecules be interconverted by rotation around single bonds? yes no conformational configurational trans (E) cis (Z) geometrical Is the isomerism at a doulbe bond? yes no optical at hicago EM 232, Spring 2010 Slide 25 25
26 E-Z Nomenclature for Alkenes igher ranked substitutuents on the same side igher ranked substitutuents on the opposite side igher Lower l Br F igher Lower igher Lower l F Br Lower igher Z configuration E configuration Groups are ranked according to atomic number igher atomic number = higher rank Z (zusammen) = together; highest priority group on each alkene carbon on same side E (entgegen) = opposite; highest priority group on each alkene carbon on opposite sides at hicago EM 232, Spring 2010 Slide 26 26
27 ahn-ingold-prelog (IP) Rules for Prioritizing (,,) (,,) (,,) Br Br l l (,,) Z (,,) (,,) E when geminal atoms are identical, compare forward atoms attached to these on the basis of atomic weight (list in decreasing order) work outward (one atom at a time) until point of difference is reached at hicago EM 232, Spring 2010 Slide 27 27
28 ahn-ingold-prelog (IP) Rules for Prioritizing (O,O,) l O 3 O O E (O,,) an atom that is multiply bonded to another atom is listed as two separate atoms for nomenclature purposes remember to list attached atoms in decreasing order of atomic weight highest priority = highest atomic weight at first point of difference at hicago EM 232, Spring 2010 Slide 28 28
29 Why Alkene Geometry Matters Geometry influences molecular shape and, in turn, physical, chemical & biological properties.... O OMe Z onfiguration MeO MeO OMe Vascular targeting agent ombretastatin A4 (A-4) MeO O OMe E onfiguration OMe OMe epi-ombretastatin A4 (A-4) Biologically Inactive! ombretum caffrum S.A. bush willow tree at hicago EM 232, Spring 2010 Slide 29 29
30 IUPA: Stereoisomeric Alkenes Steps: (E)-3-methyl-2-pentene or (E)-3-methylpent-2-ene 1. Number the longest chain. 2. Replace -ane ending of parent alkane with -ene or -en, depending on priority. 3. In the name, list the locant of only the first alkene carbon. 4. Indicate geometrical isomers with (Z) or (E) at the beginning of the name. onventions/rules: Z and E are italicized Z and E are placed within parentheses at beginning of name: (Z) & (E). cis and trans may be substituted for E/Z when alkene is 1,2-disubstituted (E) (Z) parent base alkene locant ene University of Illinois at hicago EM 232, Spring 2010 Slide 30 Lecture 8: February 4 30
31 EM 232 Organic hemistry I at hicago Relative Stabilities of Alkenes Sections
32 Relative Stabilities of Alkenes Observations: more stable = lower in energy = lower heat of combustion cis alkenes higher in energy than trans alkenes more alkyl group on alkene = more stable at hicago EM 232, Spring 2010 Slide 32 32
33 Relative Stabilities of Alkenes 1. Steric Effects van der Waals strain strain between cis groups (Z)-2,2,5,5-tetramethylhex-3-ene (less stable) (E)-2,2,5,5-tetramethylhex-3-ene (more stable) Energy Difference = 44 kjmol -1 at hicago EM 232, Spring 2010 Slide 33 33
34 Relative Stabilities of Alkenes 2. Substituent Effects alkyl groups stabilize alkenes through donation (via induction and hyperconjugation) to the more electronegative sp 2 -hybridized carbon atoms Stability R monosubstituted R R R trisubstituted R R geminally disubstituted R R R R vicinally disubstituted R R tetrasubstituted at hicago EM 232, Spring 2010 Slide 34 34
35 EM 232 Organic hemistry I at hicago Preparation of Alkenes Elimination Sections:
36 β-elimination Reactions Summary of β-elimination (1,2-elimination) Reactions 1 2 X Y α β 1 2 α β + X Y 1 2 α β Dehydrogenation 1 2 α β α O β Dehydration 1 2 α β + O 1 2 α X β Dehydrohalogenation 1 2 α β + X at hicago EM 232, Spring 2010 Slide 36 36
37 Dehydrogenation limited to industrial synthesis of ethylene, propene, 1,3-butadiene and styrene important economically, but rarely used in laboratory-scale syntheses living systems utilize enzymes to catalyze this process at hicago EM 232, Spring 2010 Slide 37 37
38 Strong Acids atalyze the Dehydration of 2 & 3 Alcohols β O 2 SO 4 O 140 º 3 PO 4 β 140 º O KSO 4 2 SO 4 and 3 PO 4 are most common acids used for dehydration: protonation of O group is first step dehydration is reversible (hydration) in aqueous acid (hapter 6) β 140 º at hicago EM 232, Spring 2010 Slide 38 38
39 Industrial Example of Dehydration NMe 2 NMe 2 NMe 2 O 2 SO 4 O O O O Tamoxifen (Nolvadex ) O Estradiol Tamoxifen mimics estrogens, such as estradiol, and inhibits their binding to the estrogen receptor in breast tissue Tamoxifen blocks cancer cell growth at hicago EM 232, Spring 2010 Slide 39 39
40 Dehydration can be oupled with Other hemical Transformation N O l F N O l F N l N Me N Me N Me Loratidine (laritin ) Two-step, one-pot transformation involves a Friedel-rafts reaction (see, hapter 12) and dehydration of the resulting 3 alcohol at hicago EM 232, Spring 2010 Slide 40 40
41 Rate of Alcohol Dehydration Mirrors Ease of arbocation Formation rate of dehydration = 3º > 2º > 1º alcohol tertiary alcohol (3º) O tertiary cation (3º) secondary alcohol (2º) O Reactivity Stability secondary cation (2 ) primary alcohol (1º) O primary cation (1 ) at hicago EM 232, Spring 2010 Slide 41 41
42 Self Test Question Predict the product for the following reaction scheme. O 2 SO º? A. B. - β + β O β - 2 O β β. D. β β β β E. no reaction University of Illinois at hicago EM 232, Spring 2010 Slide 42 42
43 Self Test Question Predict the product for the following reaction scheme. O 2 SO º? A. B. - β + or - β + O - 2 O β β β β β β. D. β E. no reaction University of Illinois at hicago EM 232, Spring 2010 Slide 43 43
44 Quiz This Week Topic = hapter 4 Bonding in Alcohols & Alkyl alides Bonding of Alkyl alides from Alcohols & X The SN1 & SN2 Mechanisms arbocations: Structure, Bonding & Stability alogenation of Alkanes Radicals: Structure, Bonding & Stablity Mechanism of Alkane alogenation University of Illinois at hicago EM 232, Spring 2010 Slide 44 Lecture 5: January 26 44
45 EM 232 Organic hemistry I at hicago Next Lecture... hapter 5: Sections Reminder - Bring ID to Exam! 45
CHEM Lecture 6
EM 494 Special Topics in hemistry Illinois at hicago EM 494 - Lecture 6 Prof. Duncan Wardrop October 15, 2012 Midterm Papers Factors that ontrol ydrocarbon Acidity Factors that ontrol ydrocarbon onformation
More information5.1 Alkene Nomenclature
5.1 Alkene Nomenclature Alkenes Alkenes are hydrocarbons that contain a carbon-carbon double bond also called "olefins" characterized by molecular formula n 2n said to be "unsaturated" Alkene Nomenclature
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 informationLecture 11 Organic Chemistry 1
EM 232 rganic hemistry I at hicago Lecture 11 rganic hemistry 1 Professor Duncan Wardrop February 16, 2010 1 Self Test Question What is the product(s) of the following reaction? 3 K( 3 ) 3 A 3 ( 3 ) 3
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 informationAlkenes and Alkynes 10/27/2010. Chapter 7. Alkenes and Alkynes. Alkenes and Alkynes
Chapter 7 Alkenes and Alkynes CHP6 Problems: 6.1-13, 16-34, 36. CHP7 Problems: 7.1-23, 25-28, 31-34, 37-39, 41-47, 49-56. Alkenes and Alkynes Alkene (or olefin ) Hydrocarbon that contains a carbon-carbon
More informationCHEM Lecture 7
CEM 494 Special Topics in Chemistry Illinois at Chicago CEM 494 - Lecture 7 Prof. Duncan Wardrop ctober 22, 2012 CEM 494 Special Topics in Chemistry Illinois at Chicago Preparation of Alkenes Elimination
More information1. Root of name depends on longest chain of C containing the double bond; ends in "ene"
Alkenes (β-carotene, an antioxidant pigment) n 2n (acyclic) n 2n-2 (cyclic) R R R R Key features sp 2 -hybridized carbons, 120 o bond angles σ + π bonding between = planar geometry around = "unsaturated"
More informationCh.6 Alkenes: Structure and Reactivity
alkene = olefin 2 2 Ethylene α-pinene 3 β-arotene (orange pigment and vitamin A precursor) 6.1 Industrial Preparation and Use of Alkenes ompounds derived industrially from ethylene 2 2 Ethylene (26 million
More informationChapter 7 Alkenes; Elimination Reactions
hapter 7 Alkenes; Elimination Reactions Alkenes Alkenes contain a carbon-carbon double bond. They are named as derivatives of alkanes with the suffix -ane changed to -ene. The parent alkane is the longest
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 informationChem 341 Organic Chemistry I Lecture Summary 16 October 01, 2007
hem 341 Organic hemistry I Lecture Summary 16 October 01, 2007 hapter 6 - Alkenes: Structure and eactivity Nomenclature Double bond geometry is important in biology. For example, the trans to cis isomerization
More informationAlkenes. Alkenes-hydrocarbons with a carbon-carbon double bond. Alkenes have the formula C n H 2n. Nomenclature
Alkenes Alkenes-hydrocarbons with a carbon-carbon double bond. Alkenes have the formula n 2n. Nomenclature Alkenes are named in the same manner as alkanes with the following adjustments. 1. Find the longest
More informationAlso called an olefin but alkene is better General formula C n H 2n (if one alkene present) Can act as weak nucleophiles
Alkenes - Structure, Stability, Nomenclature Also called an olefin but alkene is better General formula C n H 2n (if one alkene present) unsaturated - contain fewer than maximum H's possible per C Can
More informationLecture 21 Organic Chemistry 1
CEM 232 Organic Chemistry I at Chicago Lecture 21 Organic Chemistry 1 Professor Duncan Wardrop March 30, 2010 1 Self Test Question Ethanolysis of alkyl halide 1 gives ether 2 as one product; however, several
More informationChapter 6: Alkenes: Structure and Reactivity
hapter 6: Alkenes: Structure and eactivity overage: 1. Degrees of Unsaturation 2. Nomenclature cis/trans E/Z 3. Alkene Stability 4. Electrophilic Addition eactions/markovinikov s ule 5. The ammond Postulate
More informationORGANIC CHEMISTRY- 1
ORGANIC CEMISTRY- 1 ALKENES Alkenes are also called Olefins (C n 2n ) unsaturated hydrocarbons. Alkenes occur abundantly in nature. Ethylene ( 2 C=C 2 ) is a plant hormone that induces ripening in fruit.
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 informationChem101 General Chemistry. Lecture 11 Unsaturated Hydrocarbons
hem101 General hemistry Lecture 11 Unsaturated ydrocarbons Unsaturated ydrocarbons ontain one or more double or triple carbon-carbon bond. University of Wisconsin-Eau laire hem101 - Lecture 11 2 Unsaturated
More informationOrganic Chemistry 1 Lecture 5
CEM 232 Organic Chemistry I Illinois at Chicago Organic Chemistry 1 Lecture 5 Instructor: Prof. Duncan Wardrop Time/Day: T & R, 12:30-1:45 p.m. January 26, 2010 1 Self Test Question Which of the following
More informationH H C C. Alkenes C n H 2n unsaturated hydrocarbons. C 2 H 4 ethylene. Functional group = carbon-carbon double bond
Alkenes C n H 2n unsaturated hydrocarbons C 2 H 4 ethylene H H C C H H Functional group = carbon-carbon double bond sp 2 hybridization => flat, 120 o bond angles σ bond & π bond => H 2 C=CH 2 No rotation
More informationIt is possible for organic molecules with the same molecular formula to have different structures
Isomerism It is possible for organic molecules with the same molecular formula to have different structures Definition- Structural isomers: same molecular formula different structures (or structural formulae)
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 informationIntroduction to Alkenes. Structure and Reactivity
4 4 Introduction to Alkenes. Structure and Reactivity Alkenes are hydrocarbons that contain one or more carbon carbon double bonds. Alkenes are sometimes called olefins, particularly in the chemical industry.
More informationChapter 12 Alkenes and Alkynes
BR M 102 lass Notes hapter 12 Page 1 of 8 hapter 12 Alkenes and Alkynes * alkenes = double bonds * alkynes triple bonds * aromatics or arenes alternating double and single bonds such as in benzene * saturated
More information5.5 Physical Properties of Alkenes
5.5 Physical Properties of Alkenes Dipole moments What is direction of dipole moment? Does a methyl group donate electrons to the double bond, or does it withdraw them? µ = 0 D 3 µ = 0.3 D µ = 1.4 D Dipole
More informationChapter 8: Chemistry of Alkynes (C n H 2n-2 )
hapter 8: hemistry of Alkynes ( n 2n-2 ) Bonding & hybridization Both are sp-hybridized Bond angles = 180 o 1 σ + 2 π bonds Linear around lassification R R R' σ bond energy: 88 kcal/mol π bond energy:
More informationnsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes
240 Chem nsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes 1 Chapter 3 Alkenes or Olefines Crabon-Carbon double bond C n H 2n Hybridization in Alkenes: 1.34 A 2 Nomenclature of Alkenes and Cycloalkenes
More informationOrganic Halogen Compounds
8 Organic alogen ompounds APTER SUMMARY 8.1 Introduction Although organic halogen compounds are rarely found in nature, they do have a variety of commercial applications including use as insecticides,
More informationLecture 22 Organic Chemistry 1
CEM 232 rganic Chemistry I at Chicago Lecture 22 rganic Chemistry 1 Professor Duncan Wardrop April 1, 2010 1 Self Test Question Which starting material could not be used to prepare the tribromide below?
More informationAlcohols: Contain a hydroxy group( OH) bonded to an sp 2 or sp 3 hybridized
Lecture Notes hem 51B S. King hapter 9 Alcohols, Ethers, and Epoxides I. Introduction Alcohols, ether, and epoxides are 3 functional groups that contain σ-bonds. Alcohols: ontain a hydroxy group( ) bonded
More informationAlkenes. Dr. Munther A. M-Ali For 1 st Stage Setudents
Alkenes Dr. Munther A. M-Ali For 1 st Stage Setudents Alkenes Family of hydrocarbons, the alkenes, which contain less hydrogen, carbon for carbon, than the alkanes Structure of ethylene, The carbon-carbon
More information3.1 Introduction to Organic Chemistry
3.1 Introduction to Organic hemistry Organic hemistry is the study of carbon chemistry as carbon has the ability to join together in chains, rings, balls etc. arbon also joins with other elements easily
More informationChapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides"
Chapter 7 Alkenes and Alkynes I: Properties and Synthesis Elimination Reactions of Alkyl Halides The (E)-(Z) System for Designating Alkene Diastereomers The Cahn-Ingold-Prelog convention is used to assign
More informationLoudon Ch. 4 Review: Alkene Structure/Reactivity Jacquie Richardson, CU Boulder Last updated 5/30/2017
We already saw in Ch. 1 that π bonds are based on side-on overlap of leftover p orbitals. C atom C=C bond C atom orbital comes from destructive (differentcolor) interference: (note extra node) + 2p 2p
More informationCHEM J-10 June The structure of ( )-linalool, a commonly occurring natural product, is shown below.
CEM1102 2014-J-10 June 2014 The structure of ( )-linalool, a commonly occurring natural product, is shown below. 4 What is the molecular formula of ( )-linalool? C 10 18 O Which of the following best describes
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 informationeg ethylene (IUPAC: ethene), C 2
Alkenes: Structure & Properties Alkane (acyclic): n 2n+2 > saturated. Alkene (acyclic): n 2n > unsaturated. eg ethylene (IUPA: ethene), 2 4 : 2 = 2 The carbon-carbon double bond is the distinguishing feature
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 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 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 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 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 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 informationBasic Organic Chemistry Course code : CHEM (Pre-requisites : CHEM 11122)
Basic Organic Chemistry Course code : CHEM 12162 (Pre-requisites : CHEM 11122) Chapter 01 Mechanistic Aspects of S N2,S N1, E 2 & E 1 Reactions Dr. Dinesh R. Pandithavidana Office: B1 222/3 Phone: (+94)777-745-720
More informationOrganic Chemistry, Second Edition. Janice Gorzynski Smith University of Hawai i. Chapter 10 Alkenes
Organic Chemistry, Second Edition Janice Gorzynski Smith University of Hawai i Chapter 10 Alkenes Prepared by Rabi Ann Musah State University of New York at Albany Copyright The McGraw-Hill Companies,
More informationChapter 2 Structure and Properties of Organic Molecules. Advanced Bonding: Review
hapter 2 Structure and Properties of Organic Molecules hemistry 231 Organic hemistry I Fall 2007 Advanced Bonding: Review Atomic Quantum Mechanics cannot explain how molecules like 4 form: Valence Bond
More informationLab Workshop 1: Nomenclature of alkane and cycloalkanes
Lab Workshop 1: Nomenclature of alkane and cycloalkanes Each student work group choose a Leader (reads activity out loud, poses questions to group), Facilitator (makes sure everyone is participating equally,
More informationLecture 20 Organic Chemistry 1
CEM 232 rganic Chemistry I at Chicago Lecture 20 rganic Chemistry 1 Professor Duncan Wardrop March 18, 2010 1 Self-Test Question Capnellene (4) is a marine natural product that was isolated from coral
More informationOrganic Chemistry 1 Lecture 6
CEM 232 Organic Chemistry I Illinois at Chicago Organic Chemistry 1 Lecture 6 Instructor: Prof. Duncan Wardrop Time/Day: T & R, 12:30-1:45 p.m. January 28, 2010 1 Self Test Question Which form of strain
More information3.1 Organic: Basic Concepts
. rganic: Basic oncepts ydrocarbon is a compound consisting of hydrogen and carbon only Basic definitions to know Saturated: ontain single carbon-carbon bonds only Unsaturated : ontains a = double bond
More informationUnsaturated Hydrocarbons
Interchapter G Unsaturated ydrocarbons The flame from an acetylene torch. Acetylene, which is used extensively in welding, is an example of an unsaturated hydrocarbon. University Science Books, 2011. All
More information3.1 Organic: Basic Concepts
3.1 rganic: Basic oncepts ydrocarbon is a compound consisting of hydrogen and carbon only Basic definitions to know Saturated: ontain single carbon-carbon bonds only Unsaturated : ontains a = double bond
More informationHydrogen iodide is a strong acid and will drive the reverse reaction, meaning the forward reaction will not occur.
EM 261 Oct 18, 2018 Photosynthesis and Related Reactions O 2 2 O 6 12 O 6 2 O N 3, S, Fe, u, o, other Natural Products D-Glucose R O R OR Ionic substitution S N 1 & R X X 2 hv Petroleum/ Alkanes R N 2
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 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 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 information5. Reactions of Alkenes (text )
2009, Department of hemistry, The University of Western Ontario 5.1 5. Reactions of Alkenes (text 5.1 5.5) A. Addition Reactions In hapter 4, we saw that π bonds have electron density on two sides of the
More informationUniversity of Sydney Chemistry 1B (CHEM1102) Organic Chemistry Lecture Notes
University of Sydney hemistry 1B (EM1102) rganic hemistry Lecture Notes Topic 1 Introduction & isomers 2 Topic 2 Alkenes, alkynes, arenes 20 Topic 3 Structure determination 27 Topic 4 Alcohols and amines
More informationCHEM 203. Topics Discussed on Oct. 16
EM 203 Topics Discussed on Oct. 16 ydrogenation (= saturation) of olefins in the presence of finely divided transition metal catalysts (Ni, Pd, Pt, Rh, Ru...): generic alkene R 1 finely divided Pd (or
More informationPart C- section 1 p-bonds as nucleophiles
Part C- section 1 p-bonds as nucleophiles Chemistry of Alkenes (Ch 8, 9, 10) - the double bond prevents free rotation - isomerism cis and trans - nomenclature E and Z (3 or 4 different substituents around
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 informationOrganic Chemistry The Functional Group Approach. Organic Chemistry The Functional Group Approach
Organic Chemistry The Functional Group Approach OH Br alkane (no F.G.) alcohol halide alkene non-polar (grease, fats) O NH alkyne aromatic aldehyde/ketone imine linear flat Organic Chemistry The Functional
More informationCHEM Lecture 2
EM 494 Special Topics in hemistry Illinois at hicago EM 494 - Prof. Duncan Wardrop September 17, 2012 ourse Website http://www.chem.uic.edu/chem494 Syllabus ourse Policies ther handouts Announcements (ourse
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 information(1) Recall the classification system for substituted alkenes. (2) Look at the alkene indicated. Count the number of bonds to non-hydrogen groups.
Organic Chemistry - Problem Drill 10: Alkenes, Alkynes, and Dienes No. 1 of 10 1. What is the substitution pattern for alkene indicated below? (A) mono (B) di (C) tri (D) tetra (E) unsubstituted Mono is
More informationClasses of Halides. Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination. Polarity and Reactivity. Classes of Alkyl Halides
rganic hemistry, 5 th Edition L. G. Wade, Jr. hapter 6 Alkyl alides: Nucleophilic Substitution and Elimination lasses of alides Alkyl: alogen, X, is directly bonded to sp 3 carbon. Vinyl: X is bonded to
More informationChapter 5. Reactions of Alkenes and Alkynes
Chapter 5. Reactions of Alkenes and Alkynes Learning objectives: 1. Identify the followings from a reaction coordinate diagram when applicable: endothermic or exothermic reactions, activation energy, heat
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 informationOrganic Chemistry. REACTIONS Grade 12 Physical Science Mrs KL Faling
Organic Chemistry REACTIONS Grade 12 Physical Science Mrs KL Faling SUBSTITUTION REACTIONS This is a reaction where an atom or group of atoms is replaced by another atom or group of atoms Substitution
More informationReading: Chapter 4 Practice Problems: in text problems and 19 22, 24, 26, 27, 29, 30, 33 35, 39, 40.
Reading: Chapter Practice Problems: in text problems and 19 22, 24, 26, 27, 29, 30, 33 35, 39, 40. Alkenes: Structure, Nomenclature, Stability, and an Introduction to Reactivity Alkenes are unsaturated
More informationCOURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
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 informationCHEMISTRY 231 GENERAL ORGANIC CHEMISTRY I FALL 2014 List of Topics / Examination Schedule
Page 1 of 5 CHEMISTRY 231 FALL 2014 List of Topics / Examination Schedule Unit Starts Topic of Study 20 Aug 2014 STRUCTURE AND BONDING Suggested Reading: Chapter 1 29 Aug 2014 ALKANES & CYCLOALKANES Suggested
More informationOCR AS Chemistry A H032 for first assessment in Complete Tutor Notes. Section: Alkenes Boomer Publications
OR AS hemistry A 032 for first assessment in 206 omplete Tutor Notes www.boomerchemistry.com Section: 4..3 Alkenes E/Z Isomerism Alkenes Addition polymers 205 Boomer Publications page 43 page 45 page 5
More informationChapter 19: Alkenes and Alkynes
Chapter 19: Alkenes and Alkynes The vast majority of chemical compounds that we know anything about and that we synthesize in the lab or the industrial plant are organic compounds. The simplest organic
More information4.15 Halogenation of Alkanes RH + X 2 RX + HX
4.15 alogenation of Alkanes R + X 2 RX + X Energetics R + X 2 RX + X explosive for F 2 exothermic for Cl 2 and Br 2 endothermic for I 2 4.16 Chlorination of Methane Chlorination of Methane carried out
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 informationLecture 6: September 7, 2018
CM 223 Organic Chemistry I Prof. Chad Landrie Lecture 6: September 7, 2018 Ch. 4: Nomenclature of Cylcoalkanes and their Physical and Chemical Properties (4.1-4.3) Conformational Isomers of Cycloalkanes
More informationChapter 3: Structure and Nomenclature of Organic Compounds Focus on Alkanes
hapter 3: Structure and Nomenclature of rganic ompounds Focus on Alkanes rganic molecules are composed of one or more functional groups attached to one or more hydrocarbon groups (alkyl or groups) I. Functional
More informationAlkenes. Alkenes are unsaturated aliphatic hydrocarbons.
Alkenes Alkenes Each member contains one double covalent bond between two C atoms. Draw condensed structural formulas of first three members of alkenes family. Alkenes are unsaturated aliphatic hydrocarbons.
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 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 informationChapter 10 Free Radicals
hapter 10 Free Radicals This is an example of a free radical reaction. A radical is a species that has a free unpaired electron. There are several examples of stable radicals, the most common of which
More informationChemistry 210 Organic Chemistry I Fall Semester 2000 Dr. Rainer Glaser
hemistry 210 rganic hemistry I Fall Semester 2000 Dr. Rainer Glaser Examination #2 Alkyl alides: Their Synthesis by alogenation of Alkanes and Their Nucleophilic Substitution Reactions. Friday, ctober
More informationGeneral formula is CnH2n. Propene. But-1-ene. C-C pi bond. Formation of π bond in alkenes p orbitals Rotation can occur around a sigma bond
4.1.3 Alkenes Alkenes are unsaturated hydrocarbons General formula is n2n Alkenes contain a carboncarbon double bond somewhere in their structure Ethene Propene Numbers need to be added to the name when
More informationChapter 7: Alkenes and Alkynes
Chapter 7: Alkenes and Alkynes ydrocarbons Containing Double and Triple Bonds Unsaturated Compounds (Less than Maximum Atoms) Alkenes also Referred to as Olefins Properties Similar to those of Corresponding
More informationAlkenes. Bonding and Structure: Carbons in the double bond of butene are sp 2 hybridized. Side on p-p orbital overlap creates a π-bond.
Alkenes Bonding and Structure: Carbons in the double bond of butene are sp 2 hybridized. Side on p-p orbital overlap creates a π-bond. Angles around the carbons in the double bond are ~ 120º. Thus, all
More informationChapter 24 From Petroleum to Pharmaceuticals
hapter 24 From Petroleum to Pharmaceuticals 24.1 Petroleum Refining and the ydrocarbons 24.2 Functional Groups and Organic Synthesis 24.3 Pesticides and Pharmaceuticals IR Tutor and Infrared Spectroscopy
More informationA. Structure and Nomenclature. Introduction of Organic Chemistry. Unit 2: Structure of Alkanes, Cycloalkanes, and Alkenes
Organic hemistry #2 1 Introduction of Organic hemistry. Unit 2: Structure of Alkanes, ycloalkanes, and Alkenes Bring your model kits to class we will to learn to use them! Objectives: by the end of this
More informationNAME: SPRING 2015 MIDTERM
page 1 pts NAME: SPRING 2015 MIDTERM hemistry 231 Professor: Dr. Gergens take-home portion (DUE at the beginning of the period, 4/6) Do your best on this take-home portion of your mid-term. I may grade
More informationOrganic Chemistry Unit #2: Structure of Alkanes, Cycloalkanes, and Alkenes
Organic hemistry Unit #2: Structure of Alkanes, ycloalkanes, and Alkenes Bring your model kits to class we will to learn to use them! Objectives: by the end of this unit, you should be able to... Interconvert
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 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 informationGeneral Glossary. General Glossary
General Glossary Absolute configuration The actual three-dimensional structure of a chiral molecule. Absolute configurations are specified verbally by the Cahn-Ingold-Prelog R,S convention and are represented
More information4.1.3 Alkenes. N Goalby chemrevise.org. Formation of π bond p orbitals C C C C. Alkenes contain a carboncarbon. General formula is CnH2n
4.1.3 Alkenes Alkenes are unsaturated hydrocarbons General formula is n2n Alkenes contain a carboncarbon double bond somewhere in their structure Ethene Propene Numbers need to be added to the name when
More informationChapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy
Chapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy Conjugated unsaturated systems have a p orbital on a carbon adjacent to a double bond The p orbital can come from another double (e.g.
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 information75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will
71. B SN2 stands for substitution nucleophilic bimolecular. This means that there is a bimolecular rate-determining step. Therefore, the reaction will follow second-order kinetics based on the collision
More informationAlkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry
Alkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry 1 Structure and Bonding 2 Structure and Bonding Rotation around the C=C bond is restricted 90 rotation The p orbitals are orthogonal
More information