Alkynes
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ALKYNES • contains?? • general formula
C≡C Cn H2n-2
REAL LIFE EXAMPLE OF ALKYNES used as fuel in oxyacetylene torches
acetylene
REAL LIFE EXAMPLE OF ALKYNES a naturally occurring anti-viral, anti-fungal, and antibiotic compound
Thiarubine A
REAL LIFE EXAMPLE OF ALKYNES contraceptive
norethynodrel
REAL LIFE EXAMPLE OF ALKYNES antibiotic
mycomycin
REAL LIFE EXAMPLE OF ALKYNES antifungal
terbinafine
REAL LIFE EXAMPLE OF ALKYNES antiretroviral
efavirenz
REAL LIFE EXAMPLE OF ALKYNES anticancer, and nematicide
phenylhepta-1,3,5-triyne
2 types of ALKYNES + their other name + meaning of their alt names + difference
• Terminal alkynes (monosubstituted) *C≡C is nasa pinakadulo so the C≡C as a whole only has 1 substituent attached • Internal alkynes (disubstituted) *C≡C ay nasa gitna so the C≡C as a whole has 2 substituents, 1 per C, attached
PALATANDAAN in naming ALKYNES in terms of: • suffix • parent chain (straight-chain) [2]
• -yne • longest chain that passes thru BOTH C ATOMS in the triple bond (with the triple bond carbons having the lowest number) • indicate position of triple bond before the parent name
ARANGE the ff in terms of stability and energy: • alkenes • 3 types of dienes • 2 types of alkynes
MOST STABLE (lowest energy) • conjugated dienes • alkenes • isolated dienes • internal alkyne • terminal alkyne • cumulated dienes LEAST STABLE (highest energy)
PHYSICAL PROPERTIES of ALKYNES in general, are similar to ____ and ____
alkanes and alkenes
ALKYNES have slightly ______ BP & MP than alkenes
higher
WHICH will exhibit a higher BP and MP? • linear • branching
linear *more branching = bp lowers
2 WAYS of preparing alkynes
• Industrial Preparation • Laboratory Preparation
PREPARATION of ALKYNES - INDUSTRIAL • 2 ways? • what is formed?
ALKYNES formed from • Carbides • Methane
PREPARATION of ALKYNES - LABORATORY • what is formed? • ^^ how (2)?
alkynes from vicinal or geminal dihalides
PALATANDAAN in reactions in alkynes
mechanism is similar to alkenes, may exceptions or added info lang which is yung mga stated here
ALKYNES have a _____ C≡C due to?
• nucleophilic • loosely held π electrons that can be donated to an electrophile
how MANY MOLES of reagent is necessary to convert an ALKYNE into a saturated product?
2 moles saturated product = alkane so 1 mole of reagent will break 1 π bond. since alkyne has 2 π bonds (triple bond), it would need 2 moles.
4 REACTIONS of ALKYNES
• Hydrogenation • Electrophilic Addition • Acetylide ion Formation • Oxidative Cleavage
HYDROGENATION • possible reagents (3)? + steriochemistry
H2 -> Lindlar’s Catalyst: syn addition alkene Na or Li -> liq NH3: anti-addition alkene 2H2 -> Ni/Pt/Pd: tetra-substituted alkane
WHAT IF 1 mole of reagent lang ang rineact sa alkyne?
magiging alkene yung product, rather than alkane + 1 substituent lang ang ma s-substitute PER C ATOM in the C≡C IF, 2 moles kasi ang gamit, 2 substituents ang ma s-substitute PER C ATOM sa C≡C
ELECTROPHILIC ADDITION - ADDITION OF HX • what do you call the main product if 2 moles of HX is used as reagent?
• geminal dihalide (2 halogen atoms are attached to the same Carbon)