Alkynes Are Found in Natural Products
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1 Objective 13 Apply Reactivity Principles to Electrophilic Addition Reactions 2: Alkynes Identify structural features (pi bond) and electrophiles Use curved arrows to predict product
2 Alkynes Are Found in Natural Products Over 1000 natural products contain carbon-carbon triple bonds. (see Carey, Organic Chemistry, 8 th ed., p. 361) Polyacetylenes in Ginseng root: panaxynol, ginsenoyne-a, panaxydol, 10- methoxy heptadeca-1-ene-4, 6-dyne-3, 9-diol, (3R, 9R, 10R)-panaxytriol, panaxyne, and ginsenoyne-c.
3 8/22/11, CEN, p. 39 Ginseng Compound Curbs Chemo Effects Panaxytriol (Asian Panax ginseng plant) mild activity against tumors significantly alleviates the weight loss and nerve damage associated with cancer treatments in mice
4 2/13/12, CEN, p. 41 Behind A Mushroom Scourge: Scientists search for the compounds responsible for unexplained deaths The deadly mushroom Trogia venenata Zhu L. Yang may have claimed hundreds of lives.
5 Acetylene is Prepared by 3 Industrial Methods 1. Thermal Cracking of Natural Gas (Methane) 2 CH o C -- > C 2 H H 2 2. Dehydrogenation of ethylene: H 2 C=CH 2 -- heat --> C 2 H 2 + H 2 3. From Lime and Coke: CaO + 3 C à CaC 2 + CO CaC H 2 O o C -- > Ca(OH) 2 + C 2 H 2 Acetylene is Used: 1. Welding (combustion of oxyacetylene flame = 3300 o C; hottest burning fuel gas). 2. C 2 H 2 ---> C 2 H 4 ---> plastics 3. A Starting Material To Make Many Organic Compounds Reppe Chemistry ( C 2 H 2 ---> vinyl compounds, acrylic acid/ester
6 4 Types of Organic Polar Reactions
7 Alkynes Have 2 π Bonds and Act Like Alkenes Functional group/bonding/structure/reactivity: C C H Reactions: Acid-Base Reaction: Ethane, Ethylene, Acetylene can lose a H + Why is C 2 H 2 the strongest acid? (Hint: see conjugate base stability) Addition Reaction: Alkynes are More Reactive than Alkenes Alkyne π Bond is more Nucleophilic than Alkene π Bond. Why?
8 Alkynes Have 2 π Bonds and Act Like Alkenes Functional group/bonding/structure/reactivity: C C H Compare ethane to ethylene to acetylene. Longest carbon-carbon bond? (i) ethane (ii) ethylene (iii) acetylene Hybridization at each C? ethane (a) sp (b) sp 2 (c) sp 3 ethylene (d) sp (e) sp 2 (f) sp 3 acetylene (g) sp (h) sp 2 (i) sp 3
9 Alkynes are Used as Starting Materials to Make Many Compounds Alkyne Addition Reactions Are Similar to Alkene Addition Reactions A-B = H 2, HX, X 2, HOH
10 Addition of H 2 : Hydrogenation of Alkyne Produces an Alkene or Alkane Carey, 8th ed., #9.25a, b
11 Carey, 8th ed., #9.25g, h Addition of HX Produces Alkyl Halide or Dihalide with Excess HX
12 Addition of X 2 Produces 1, 2-dihaloalkene Is cis or trans alkene formed? Carey, 8th ed., #9.25i, j
13 Addition of HOH (H 2 SO 4 (aq) and Hg 2+ catalyst) Produces an Enol Alkyne Addition with a twist: Enol Tautomerizes into a Ketone Draw resonance structure of enol. Carey, 8th ed., #9.25k and 29g
14 Ozonolysis Produces Carbonyl Compound (C=O) Alkene + O 3 --> Aldehyde/Ketone Alkyne + O 3 --> Acid or CO 2 from terminal alkyne Use in Synthesis: reduce chain length, make carbonyl Carey, 8th ed., #9.25l, 29e and f
15 Alkyne Addition Reactions Are Similar to Alkene Addition Reactions Predict the product(s) of the following reactions: Reaction Conditions H 2 /catalyst HX Alkene: Propylene Alkyne: Propyne X 2 H 2 O/H + catalyst O 3 / H 2 O
16 Ethylene has a pk a of 44; acetylene has a pk a of 25. Acetylene is a acid than ethylene; the conjugate base of acetylene is a base than the conjugate base of ethylene. a. stronger/stronger b. stronger/weaker c. weaker/stronger d. weaker/weaker
17 Acetylene is a Very Weak Acid Acetylene is a Stronger Acid than Ethylene Acetylide Ion is a Very Strong Nucleophile Acid-base: Acetylene is Weakly Acidic. pk a of acetylene = 25 pk a of ethylene = 44 pk a of ethane = 50 Which base reacts with acetylene?
18 Which base reacts with acetylene? Draw the structure of the products of the reaction. a. H 2 O b. OEt - c. NH 2 -
19 The Acetylide Ion (HC C: - ) is a Very Strong Nu: - Acetylide ion is used in Synthesis: Acetylide Ion reacts with R-X in a Substitution Reaction Starting from acetylene, suggest a synthesis of 2-butyne.
20 The Acetylide Ion is Used to Make C-C Bonds Synthesis: Acetylide as an Alkylating Agent to Lengthen Chain Starting from acetylene, suggest a synthesis of 2-butyne. Acetylide ion undergoes substitution with: (i) 1 o RX (ii) 2 o RX (iii) 3 o RX What is the mechanism type? (iv) S N 1 (v) S N 2
21 The Acetylide Ion is Used to Make C-C Bonds Synthesis: Acetylide as an Alkylating Agent to Lengthen Chain Acetylide reacts with 1 o RX via S N 2 mechanism. Use CH 3 OH instead of CH 3 I. Will same product form? Give reasons.?? Carey, Organic Chemistry, 8 th ed., #9.25d and e, 29a and d.
22 Making C-C Bonds Is Important in Synthesis 1. Acetylide ion: HCC: - + R-X à Nobel Prize in Chemistry: Grignard reagent (Chem 12B) RMgX + aldehyde/ketone à Nobel Prize in Chemistry: Pd catalyzed cross coupling Chemical and Engineering News, 10/11/10, p. 7.
23 Acetylide Ion is Used to Form C-C Bonds (Lengthen Chain) Alkynes Undergo Addition Reactions
24 Acetylene or Ethylene is Often used as a Starting Material in Synthesis Alkynes can be Converted to Alkenes which can be converted to Alkanes Many Syntheses Start from an Alkene or Go Through an Alkene to make the Target compound (alkene as hub ) Acetylene is used to Lengthen a Carbon Chain (via Substitution Rxn) Klein, Ch. 10#53
25 Alkynes Are Like Alkenes Alkynes, like Alkenes, are Prepared via Elimination Reaction Alkynes, like Alkenes, undergo Addition Reactions Alkynes are Stronger Acids than Alkenes ===> Acetylene (HC CH) + B: - ---> Acetylide ion (HC C: - ) The Acetylide ion (HC C: - ) is a very good Nu: - ===> used in Substitution reactions ===> used to make C-C bonds
26 Alkynes are Like Alkenes How do you make an alkene? How do you make an alkyne? What is the alkene addition product? What is the alkyne addition product?
27 Lab: Alkynes are Prepared by an Elimination Reaction from a Dihalide Elimination Reaction: R-LG + Nu: - --> alkene + Nu-H + LG - What LG is used? R-LG 2 + NaNH 2 à alkyne + Nu-H + LG - where LG = X 2 2 Vicinal dihalide = X on adjacent C Geminal ( twins ) dihalide = X on same C Carey, Organic Chemistry, 8 th ed., #9.22a, 29b and c
28 Which method does not work to make acetylene?
29 Add Alkyne Reactions to your Organic Reaction Map Note: Alkenes are the hub to make different groups Klein, 1st ed., #10.40 and 41 and 46 and 52 Carey, 8 th ed., #9.21, 22b, 23c, 24, 31, 33, 34, 36
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