Organic Flashcards
מהן התרכובות האנאורגניות?
CO carbon monoxide CO2 carbon dioxide CO3 2- carbonate CaC2 calcium carbide HCN hydrogen cyanide CN - cyanide CaCO3 calcium carbonate HCO3 - hydrogen carbonate
וכל מולקולה שלא מכילה C וH
למה פחמן מיוחד?
- יוצר קשר בודד או כפול או משולש
- אלקטרושליליות 2.5 - מגיב אבל גם לא מגיב
- מסוגל ליצור ארבעה קשרים
איזה קשר חזק יותרת פאי או סיגמה?למה?
סיגמה בגלל שבפאי יש נוד למרות שיש אוברלאפ בשתי נקודות
כמה מעלות יש בין 2 קשרי פאי?
90
Aromatic definition
Fully conjugated and cyclic, floows Huckle’s rule
What is Huckle’s rule
nr of pie electrons= 4n+2 (n-nr. of rings)
What are the three sucategories of aromatic compounds?
homo (benzene), hetero (pyridine), fused (naphthalene)
What are the three sucategories of aliphatic compounds?
saturated (alkanes), unsatureated (alkenes, alkynes)
What atoms can participate in the chemical reaction of benzene? What type of chemical reaction is it?
SE- SON
Increasing bond strength of alkene benzene alkyne alkane
alkane
Where do carbons always have the same hybridization? which?
Alkane (SP3), benzene (SP2)
Where do carbons have different hybridizations? which?
Alkenes (SP2) except: 1. Only SP2 H2C=CH2 - ethylene
2. Only SP2 (when fully conjugated) H2c=CH-CH=CH2 - like 1,3 butadiene
Alkynes (SP) except: Only SP HC=CH -acetylene
Degree of carbon
primary- attached to only one carbon
secondary- “ “ two carbons
tertiary- “ “ three “
quaternary- “ “ four “
Priorities of naming- alkanes
- longest carbon chane
- end closer to abranch gets lowest nr.
- alphabetically
- terminal with more branches
What are structural isomers?
same molecular formula, differenet connectivity
IUPAC
international union of pure and applied chemistry
Isomers of alkanes
4 carbons- (Two) IUPAC- butane, 2-methyl propane
Common- n butane, isobutane
5 carbons- (Three) IUPAC- pentane, 2-methyl butane, 2-di methyl propane
Common- n pentane, iso pentane, neo pentane
6 carbons- (Five) IUPAC- hexane, 2-methyl pentane, 3-methyl pentane, 2 3-di mythyl butane, 2 2-di methyl butane
Common- n hexane, iso hexane, X, X, neohexane
Isomers of alkyls
3 carbons (Two)- n propyl, iso propyl 4 carbons (Four)- n butyl, sec butyl, tert butyl, iso butyl
What does the BP depend on?
nr. of branches (less is better)
nr. of carbons (more is better)
surface area (bigger is better)
OH groups (more is better)
What are the three chemical reactions?
Addition (combination)
Substitution (exchange)
Elimination (decomposition)
What are the two mechanisms of reactions? what are thier products?
homolysis- radicals
heterolysis- ions (cations or “ium” ending- lewis acid, anions or “ide” ending- lewis base).
Alkane reaction example
SR halogenation (chlorination)
CH4+nCl2= CH3Cl+1HCL –>chloro methane / methyl chloride
CH2CL2+2HCL –>di-chloro methane
CHCl3+3HCl –>tri-chloro methane / chloroform
CCl4+4HCl –>tetra-chloro methane / carbon tetra chloride *excess\enough/4 moles
(=organic+inorganic)
uses light to occur
This happens in two steps! 1. light activates halogen 2.activated halogen activates alkane 3. alkyl can be radical לשרטט
combustion
full oxidation organic–>inorganic
CxHy + (X+Y/4)O2 = (Y:2)H2O + (X)CO2
What are the two components of gasoline?
8C good- octane\ 2 2 4-tri methyl pentane
7C bad- heptane unbranched
What kind of isomers are alkenes and cycloalkanes?
structural isomers
In which type of hydrocarbon is the ideal angle equal to 109.5 and how is it called?
What other angles are there?
What is the difference between them called and how does it effect the stability of the molecule?
cycloalkanes
normal angle
abnormal angles- 60, 90, 108, 120
angle strain –> when it increses the molecule will be less stable.
What affects the stability of cycloalkanes?
- angle strain.
2. “intramolecular stains” \ “non-bonded interactions” (repulsion between hydrogen atoms).
What two conformations are there in alkanes? How can a molecule change between the two?
staggered (stable) –> eclipsed (less stable)
by activation energy
the other way by rotation
What are the special conformations in cycloalkane structures?
cyclo pentane: envelope(more stable), half chair(less stable).
cyclo hexane: chair(more stable), chair(less stable).
*only chair has equatorial hydrogens.
Which position of hydrogen is most stable?
equatorial rather than axial
What is more stable cis or trans, equatorial or axial?
trans, then equatorial
ylene
ending of common name of alkenes
allene/diene
allene cummulated dienes
diene- conjugated or isolated dienes
what is another name for benzene?
1 3 5-cyclo hexa triene
vinyl
the only alkene branch! CH2=CH-
equals ethene minus 1H
CH2=CH-
vinyl, the only alkene branch
equals ethene minus 1H
How many isomers does C4H8 have?
6 overall
cycloalkanes: cyclo butane, methyl cyclo propane
alkenes: 1-butene, iso-butene, cis 2-butene, trans 2-butene
How many isomers does C5H10 have?
10 overall
cycloalkanes: cyclopentane, methyl cyclo butane, 1 2-di methyl cyclopropane, 1 1-di methyl cyclopropane, ethyl cyclo propane.
alkenes: 1-pentene, 3-methyl 1-butene, iso- pentene, cis 2-pentene, trans 2-pentene.
What effects the stability of alkenes?
- double bond in the middle is more stable than on the side
2. trans more stable than cis
Name the types of AE reactions, in which type of molecule do they occur?
alkenes, alkynes, cycloalkanes,aldehydes, ketones.
- halogination X2 (draw bromination of 1-butene)
- hydro halogenation HX (adding HI to propene)
- hydration H2O (hydration of 2-chloro 2-butene)
Name the types of AR reactions, in which type of molecule do they occur?
alkenes, alkynes, cycloalkanes.
- hydrogenation H2 (hydrogenation of ethene)
- polimerazation (of chloro ethene / vinyl chloride *creates poly vinyl chloride- PVC- plastic)
Markovnikov’s rule
In AE reactions, hydrogens will tend to attach to the atom with most hydrogens.
What is natural rubber made of?
A polimer of isoperene, created in the process of AR of an alkene.
What is plastic made of?
A polimer of vinyl chloride, created in the process of AR of an alkene.
What is polyisopene?
natural rubber
What is poly vinyl chloride?
plastic
4 important unsaturated polimers
- polyisopene- rubber (isolated).
- b carotene- in carrots (conjugated) 18C.
- retinal- also called rhod, prostetic in rhodopsin which is a protein in the eyes -aldehyde (conjugated). (b one ion ring + fully conjugated 9 carbon chane with two methyl groups + an aldehyde group) **created from oxidation of precursor.
- retinol- vitamin A1 -alcohol (conjugated). (b one ion ring + fully conjugated 9 carbon chane with two methyl groups + an alcohol group). **created from reduction of retinal.
What is a protein made of?
Holoprotein:
- prosthetic group- non protein
- apoprotein- only protein
hemoglobin protein
prosthetic- heme
apoprotein- globin (2 alpha, 2 beta)
conected by a binding site
rhodopsin protein
prosthetic- rhod \ retinal (b one ion ring + fully conjugated 9 carbon chane with two methyl groups + an aldehyde group)
apoprotein- opsin (ring, lys-basic charged NH3+
connected to the oxygen of an aldehyde in the prosthetic group by schiff base linkage C=N (dehydration)
Vitamins- fat soluble and water soluble
fat soluble: DEAK
D3- bones E-antioxidant A1-vision K1-blood clotting
water soluble: CB
C- “askorbic acid” immune
B- “niacin” / “nicotin acid” B1-thiamine B2-riboflavin B6-pyridoxal B7-biotin B9-pholic acid B12-coblamin
acetylene, way of prodduction, uses
common name of alkyne H-C—C-H
CaO (lime) + 3C (coke/coal) –> CaC2 (inorganic) + CO(inorganic
CaC2 + H2O –> C2H2 + Ca(OH)2
OR
by partial oxidation of CH4
used for lightning, welding
**combustion of acetylene is very exothermic
H-C—C-H
acetylene
Which molecules have equal BP if they have similar masses?
alkynes and alkanes
Are alkanes or alkynes more acidic? why?
alkyne (SP) rather than alkane (SP3) becuse alkynes have more S characteristics, and therefore it will be easier to extract hydrogens.
sextet nr.
nr of pie electrons in Huckle’s rule
hoe many lone pairs of electron do the following atoms have? SON
S, O- 2
N- 1
What are the three famous non aromatic cyclic molecules?
piperidine, indene, pyrolidine
What is the name of benzene as a branch?
phenyl
How many isomers are there for a benzene with two branches?
Three (o,p,m)
How many isomers are there for a benzene with three branches?
Three (123, 124, 135)
How many isomers are there for a benzene with four branches?
Three (234 ,235, 246)
List the ortho-para directors. How is the precentage divided between them?
The seven ortho-para directors:
R-N-R, H-N-R, X(halogen), OH, R(alkyl), R-O(alkoxy), NH2(amino).
*All activating except from X
ortho-63%
para-34%
List the meta directors.In which reactions do they exist? How much is the precentage?
The five meta directors in reactions of benzene:
COOH(carboxylic acid),CHO(aldehyde), CN-(cyanide), NO2(nitrogen dioxide), SO3H(sulfonic acid).
*All activating
93%
Increasing speed of types of directors
meta deactivating
What are the five benzene reactions? What are their mechanisms?
Always SE
- Halogenation
- Alkylation
- Acylation
- Nitration
- Sulfonation
IUPAC and common naming of halogen containing compounds
IUPAC halo+alkane
common alkyl+halide
What are the three types of halogen containing compounds?
- alkyl halide (attached to a SP3 hyberdized carbon)
- vinyl halide (attached to a SP2 hyberdized carbon)
- aryl halide (attached to a SP2 hyberdized carbon in an aromatic ring)
Degree of halogen containing compounds, their stability
Is determined by the number of carbons that the carbon which is attached to a halogen is attached to.
1 degrees is the least stable while 3degrees is the most stable.
How are the following compounds called:
- Halogen attached to a SP3 hyberdized carbon
- Halogen attached to a SP2 hyberdized carbon
- Halogen attached to a SP2 hyberdized carbon in an aromatic ring
- alkyl halide
- vinyl halide
- aryl halide