lOMoARcPSD|6228193

‫תינגרוא הימיכב תואצרה םוכיס‬

Introduction to Organic Chemistry (‫ןב תטיסרבינוא‬-‫)בגנב ןוירוג‬

StuDocu is not sponsored or endorsed by any college or university

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 lOMoARcPSD|6228193

arbely@bgu.ac.il – :

( . –
. . .)
𝑎 . 𝑐ℎ𝑎 𝑔𝑒
+ ' = ' . ' = ' 𝑎 𝑖𝑐 .𝑋 :
' ' –
. –
.' 8 = –
. '
. –

. ) ( –
.
. –
. . –
. – –
.) (

)+δ( , –

)-δ( –
. –
:

, \ 1 Figure

,-δ +δ . . –

Dipole moment=e*d .

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 lOMoARcPSD|6228193

:) ' (

– •
– )Br, I, Cl, F( •
– •
– •
– •
. –
. –
S .0 –
.p

. –

- ' - 2 Figure

. –
. . –
.
.sp s p . –

. – – sp3

. . – sp2

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 lOMoARcPSD|6228193

. ,) ( . –
.sp 3

: -

– •
– •
:

. – •
. – •
– – Ka
.
. , ,

.)AH( – pH<PKa •
.)-A( – pH>PKa •

CnH2n+2 : .

3 Figure

ane : . , –
.R .CnH2n+1 : .yl

. . – •
. . – •
. . – •
: .IUPAC "

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 lOMoARcPSD|6228193

= Iso - 4 Figure

. – .1
. .2
, '
.
. di, tri, tetra .3
.methyl ethyl , ,)di,tri( ,a,b,c .4
a,b,c , .5
.
. , .6
. )iso, tert( .7

CnH2n : .

. .1
,1 – .2
.a,b,c .
: 3 .3
.

: . ,
.ene ane

, .1
.
.diene .2
.a,b,c " , " – .3
. .4
,1 – ' – .5
.
. –
–

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 lOMoARcPSD|6228193

: ,

– . . –
. , , .
C-O-C – ethers –

.oxy

. ,
. .OH

(. .1
.) , ,
. .2
."diol" ."ol" .3
. – .4
.

. , , "
.

,) ( .1
.amine
.N , .2

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 lOMoARcPSD|6228193

- .
. ,
, . ,
.
-
.Z=N, O, F, Cl, Br R-C-Z .
. - - .

' . . -
.)N, O, F - ( .
. –
.
–
' .) - - < > (
.
. –
. .
–
. - - – .
, . '
, ' .
. '

. .
. ' –
.
. –
. –
.
. – \
. . –
.
:

. . 180 – Staggered •
:2-
. – Gauche o

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 lOMoARcPSD|6228193

. – Anti o
.
– eclipsed •

. –
. –

Br2 . σ
: ,)hv( )Δ( " " ,) ( Cl2

2 – )Hetrolytic( .1

: 2 .

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 lOMoARcPSD|6228193

. – )Homolytic( .2

: .
. *

.) ( – Initiation step •
.
, " " – Propagation step •
CH3Cl+Cl :
.
.
. , : " " •
: – Termination step •
. o
. o
( o
.)
. .
, 4- 6 – Butane '
40%- 60%
. , 71%- , .
.
.
– )Stereochemistry(

. – isomers – •
)ethanol, dimethyl ether – ' ( – o
:2 . – o
- ▪
2- . - ▪
– )Enantiomers( •
.

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 lOMoARcPSD|6228193

– )Diastereomers( •
.

. – )Chiral object(

. – -
. -
. ) 4- ( -
. . –
. . 180

- . . : - 5 Figure
:
.

, -
.
:
, ,) ( ,
.
1 " 10
.

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 lOMoARcPSD|6228193

x . –
. 0 , x
.
.

) ( –
. – .1
. 2- ,
. 1- 4 .2
– .R – 2- 1- .3
.S
. R .4
. . S R
! 3 .5
.

R S( – 4 . – 4 1 –
.)
! S- R

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 lOMoARcPSD|6228193

3- 2 ' , 4- 3 , 2- 1 6 Figure

2 – meso compound

, –
.) 2( 3 ,
: –
(2S, 3R) 3-Bromo-2-butanol

.R 3 S 2

, –
.
. .
. , ,
. –
. , ' – '
. –
. –
. ' –

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 lOMoARcPSD|6228193

.
.)A…..B.....C( .

7 Figure

– •
.
– )Exeergonic( •
. ,

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 lOMoARcPSD|6228193

– )Endergonic( •
. –
. ,
( ,
.)
. -‡
:

. - •

. - •

.) ( :2-
.)F, Cl, Br( X

– – SN2 •
.
– – SN1 •
.
.
SN2

. •
. , •
: •
. –
. – rate=k[alkyl halide][Nu-] •
.) ( •
– •
. .

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 lOMoARcPSD|6228193

. ,tert ,' . ,
.methyl halide>1 alkyl halide>2 alkyl halide :
o o

.
? •
, . o
. .
!
. o
. ,

- 8 Figure

•
. – .
2 2
.0 –

S R, •
.

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 lOMoARcPSD|6228193

, 9 Figure

.) F ( ,
. , ' :
.) (
. , – "
, , :
. ,
.
) ( .
.SN2

- SN2 Mechanism

.) ( –
( –
.)
.
.) –' ( = = –

:
) ( ' – - -
' . – - -
.
, , ' . - Nu-
, " " ,
. -
, .DMSO ,DMF :
. " " - ,
: , 7'
. -
. -
. - -

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 lOMoARcPSD|6228193

– ( -
.)

, –
.) – (
,) (
.

10 Figure

, ,
, . ,
.

OH- . , - 11 Figure
.

SN1

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 lOMoARcPSD|6228193

:
. - -
. - -
.) 2( -
: 2- SN1

. - .1
. .2
.

- . - 12 Figure

" ( . - . - - 13 Figure
)

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 lOMoARcPSD|6228193

4.4.16

. . SN1

–
.) – ( –
: - SN1 ,

. , - .1
- .

.2
- 14 Figure

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 lOMoARcPSD|6228193

– – .3
.
.

.4
? .
:

. – Endergonic Reaction –I

. – – II

. – Exergonic Reaction – – III

– )Hammond postulate(
.

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 lOMoARcPSD|6228193

: -

- 15 Figure

. .
SN2 . – –
. 2 SN1 .

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 lOMoARcPSD|6228193

\ . - 16 Figure

, 50-50 ,
(
.)
,SN2 –
.

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 lOMoARcPSD|6228193

- . - 17 Figure

–
. –
. ) (
! ,

- 18 Figure

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 lOMoARcPSD|6228193

. ,

. –
. –
.
.Allylic : .)Vinylic(
,
.
. SP2 :
: , p ,

:cis-trans ,

sp2 2 – cis

. 2 – trans

- - 19 Figure

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 lOMoARcPSD|6228193

. ,
.
. ,
. ,
:E,Z ? -

.1
.Z – .2
.E – .3

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 lOMoARcPSD|6228193

.)H>D( .) ( :

6.4.16
.) ( *
.sp2 *

.) –

= , 20 Figure

. ? .
–
.
. – –
.

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 lOMoARcPSD|6228193

.
. –

. ,
: 2-
. .) ( .1
. .2

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 lOMoARcPSD|6228193

:
. ) ( .1
.) ( .2
Br- .3
. ,
: 2

. . –
. ,
. – ' *
:' .

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 lOMoARcPSD|6228193

, – *
*
. '
. –
= . sp2
.
. ,
– )H2SO4(
.
. "
, .
.

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 lOMoARcPSD|6228193

, " -
.
,) ( ) (
. , .
. –
.
. –
.
. . \
.

. , –

, , 21 Figure

. –

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 lOMoARcPSD|6228193

22 Figure

. 23 Figure

: 2- " " , 6 5
-
-
. , !
11.4.16
.)Br2, Cl2(
.
,).. , ( " "
.

. . 24 Figure
.) (
.) (

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 lOMoARcPSD|6228193

, -
( .
. )
?)2Br- ( -
. Br +

. ) (
, –
. .

, ,) ( .
( ,
.)

,) (
: .

+ , . 25 Figure
‫מצב המעבר‬ .

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 lOMoARcPSD|6228193

. –
. – Pt/C

. " " ) (
.

. ?S R . 26 Figure

- . -" " 27 Figure

, .
.) (S R ,

, 28 Figure

2 – Syn

. – Anti

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 lOMoARcPSD|6228193

. .Syn 29 Figure

) ( . Cis 30 Figure

: anti –

trans 31 Figure

." " trans cis

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 lOMoARcPSD|6228193

, . " "
.
E2

:
, ,
. ,

. –
.
:
. –
. –
, –) (
RI>RBr>RCl>RF :

–) ( '
.

, . , 32 Figure
. Z ,E

13.4.16
. :
. 55 :

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 lOMoARcPSD|6228193

E2

.
. ,
.
. , ,

– – )Zaitsev( '
: .

,)C=C-C=C( - - – •
: .

! –
– , – •
:

– ( , – •
: , .)

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 lOMoARcPSD|6228193

. ,
. , ,

33 Figure

E1

: 2-
. -
. -
, . –
.

.
,) H ( ,
:

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 lOMoARcPSD|6228193

. – '

:
. , .
. –
, .
.

: .
. .E2

E2

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 lOMoARcPSD|6228193

. p
eclipsed , .
.staggered\anti

:
eclipsed – Syn -
staggered anti – Anti -

, : 2- Anti
.) (

) ( 34 Figure

.anti 2 , 2
:

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 lOMoARcPSD|6228193

. anti .eclipsed anti 35 Figure

. – trans

2.5.16
. –
E1

2 , , 2-
. .

SN2/E2 SN1/E1 .1
. \ SN2/E2 .a
. \ – SN1/E1 .b
. \ \ .2
SN2/E2 .a
, : , .i
. –

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 lOMoARcPSD|6228193

( –
.)

. – .ii
.
.iii
SN1/E1 .b
.1 .i
. – .ii

2 –
–
. ,
. –

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 lOMoARcPSD|6228193

, . – OH-
: .H2O+

.)OH2+( ,
.
.SN1 .

HBr , 36 Figure

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 lOMoARcPSD|6228193

. SN2

.
.
:) (

: –

.
:H3PO4 H2SO4

- 37 Figure

. *
. – 2
,) (
.
–) (
.
, ,
' ( .
.) ,
. –
4.5.16 –

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 lOMoARcPSD|6228193

. – *
. –
.
. ,
E1

– –
.
E2 & SN2

. –
.
.
. "

.SH

' . ,
.
–) ( RS- ,
.) OH- (
.) ' (
.)R-S-R( –

.) (
. .

. 38 Figure

. – R-MgX – )Grignard reagents(

R-+MgX+ :

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 lOMoARcPSD|6228193

39 Figure

. , •
•
.
- 9.5.16
. –

– ( .C6H6 . –
p ,sp2 . .)
p . p
. pi .

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 lOMoARcPSD|6228193

– 40 Figure

: ,

. – resonance contributor
. resonance hybrid ,

,
:

.208 360 " ,120 41 Figure

. -

!
.

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 lOMoARcPSD|6228193

:
' – . .1
:p .

42 Figure

.) ( –
:

. •
.) ( •
. ' •
•
.sp3 .) (

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 lOMoARcPSD|6228193

. .sp2 . 43 Figure

- 44 Figure

,) ( sp2 45 Figure
. .

. '
. p sp
: ,p

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 lOMoARcPSD|6228193

46 Figure

. ?
. , .
?

– •
:

A . A , 47 Figure
.

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 lOMoARcPSD|6228193

16.5.16
! , :
sp3 :2

? ? .
.
:
. . .1
. .2

O G . Figure 48

( .3
.) ,
: -
. .1
. .2
. .3
. .4

?
,
.
–)delocalization energy(
.
! ) (

, •
.
2 ( , •
.)1
. , •

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 lOMoARcPSD|6228193

2 - 49 Figure
, , ( .
)

. –
.
–

. - 50 Figure

- 51 Figure
. .

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 lOMoARcPSD|6228193

. - . 6 52 Figure
Pka=10( , ,
. .)16

. - PKA 53 Figure
.

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 lOMoARcPSD|6228193

- 54 Figure

, . –
) ( sp3

– )polyenes(

, ' -
. , HBr
.
.1,4 1,2 – 2 –

- 2 55 Figure
1- .4 2

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 lOMoARcPSD|6228193

. 1- -) - ( 56 Figure

.)Br2 ( 1,4 1,2

:
.
.
.
. – 1,2
.) ( 1,4

. , 57 Figure

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 lOMoARcPSD|6228193

. ,
. =

' 58 Figure

. ' '

. !!!1,4 59 Figure
.

. , –

. ,) ( , . –
.
.' ,)! ( –
.)' (

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 lOMoARcPSD|6228193

– 18.5.16
. –
. .
:
, .1
.
.)3 -' ( .2
, –
.)0 = n( )4n+2(

: ' . –

2 . 2 – cyclopentadiene
:) ( . .

VSEPR . 6 , - 60 Figure
.sp3

. sp3 – cyclopropane
: sp 2

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 lOMoARcPSD|6228193

: –

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 lOMoARcPSD|6228193

. - 61 Figure
. , ,

– pyrrole

62 Figure

.sp3 , – – Furan
:

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 lOMoARcPSD|6228193

. .. - 63 Figure

, , cyclopentadiene
: .

. - 64 Figure

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 lOMoARcPSD|6228193

, : 65 Figure

:
)R-OH :' ( \ –R

)Ar-OH :' . ( – Ar

. – Phenyl

. –

– •

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 lOMoARcPSD|6228193

. . B - 66 Figure
, 2 . "
.

: .

. 5

. . , 3 67 Figure

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 lOMoARcPSD|6228193

)FeBr3 FeCl3( . – )1

?Cl2 Br2 68 Figure

. . 69 Figure
. !

. FeBr3 ,

23.5.16
– .2
= NO2

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 lOMoARcPSD|6228193

, 70 Figure

. )NO2+( ,
.
: ,

.3
: 2 "

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 lOMoARcPSD|6228193

- 71 Figure

72 Figure

.
: -

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 lOMoARcPSD|6228193

) - ( 73 Figure
.

. :
.

– )Friedel-Crafts acylation( .4

- )acyl(

R=CH3

.
: 2-

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 lOMoARcPSD|6228193

AlCl3 : 2- 2 74 Figure

: –

- 75 Figure

) ( ,) (
.AlCl3

.
)Friedel-Crafts alkylation( .5

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 lOMoARcPSD|6228193

76 Figure

. ,
?
: –

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 lOMoARcPSD|6228193

.
:) (

. – )Ortho( •
. – )Meta( •
. – )Para( •

! – –

? . –
?
. –
. –

: ?
. – )inductive electron withdrawal( .1

, – .2
.

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 lOMoARcPSD|6228193

: – .3

.sp2 - . 77 Figure

78 Figure

. –

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 lOMoARcPSD|6228193

79 Figure

– – •
.

, - 80 Figure
! ,

– •
.

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 lOMoARcPSD|6228193

. . – •

– - •
.
. - .

81 Figure

– – - •

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 lOMoARcPSD|6228193

– , , – - •
.) (
. sp3

:
.
.
? .

, ! 82 Figure
.

. ,
. ) (
. "

: -

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 lOMoARcPSD|6228193

25.5.16 –
. .X Y ,Y X

– \
.)Y(
,
. .
–

. –
.

) (
:) – ( \

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 lOMoARcPSD|6228193

. \
: \ -
. \
.
. \
: ,

:
. \ -
. \ -

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 lOMoARcPSD|6228193

. ) ( -
:pKa

pka pka : '

:
, -
.
, -
.
: \
. ,) (
:

: – – 2

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 lOMoARcPSD|6228193

. 83 Figure

– C=0 . C=O 84 Figure

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 lOMoARcPSD|6228193

: .oic acid R

. – HCOOH -
. – CH3COOH -

.)O (

) ( .1 , "
. :
: ,

( 2 " –
:)

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 lOMoARcPSD|6228193

. ) ( *
.
. – - \ . 2- –
.
– R' (R –
. .)R

:)oic acid ( ate " R'

. ,) ' ( ate

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 lOMoARcPSD|6228193

.W=NH2, NHR, NR2 –

:amide oic acid

N 85 Figure

,) – (
)carboxylate(

:carboxylate

: : .1

. 86 Figure
.

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. – .2

.
.
:protonated :

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. .
.

sp2 87 Figure

. '
–
.
' , –

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 lOMoARcPSD|6228193

:
:

Y( , - - 88 Figure
)Z

sp2 ! sp3 –
.
.

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 lOMoARcPSD|6228193

30.5.16
.)Y(

. ,
. –

. ,
, + :
.

. . 89 Figure

90 Figure

Y ( , ,
:)Z

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:) (

91 Figure

. , , . 92 Figure
.

. -

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. " . 93 Figure

:
:) ( – .1

) ( .2

. - 94 Figure

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.2 – .3
) ( .4
NHRR' ,NH2R ,NH3 : . - NR3

) ( .1

) ( . - 95 Figure

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-2 96 Figure

– .1

. " -

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( – -
, .)
.
. – -
. - - -
, ( – -
. .)
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.)OH-
. – -
.
: ,

. ?
: ) (

.)OH-( -
.) ( -
, -
.

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: . 2- :

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6.6.16
.
)Transesterifiaction(

. .
: – 3– –

. –
. –

. –
: –

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.
!
:

. .
.PBr3 SOCl2
:) (

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97 Figure

–
:) (

98 Figure

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:R

- 99 Figure

. '

. ,1 ' .al –

.one –
.)3-hexanone ' ( ,

:) (

- 100 Figure
– . . ,
.

:
. .1

\ 101 Figure

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. ,) =( Z
.

- 102 Figure

.2
: ,O N' – )lone pair( Z

' 103 Figure

: – )grignard reagents( -

– 104 Figure

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105 Figure

. ,
. – -
: –

–
:
.

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, . 106 Figure
.
.

.3
' ' : -
. ' ' – .
: (-H(

. 107 Figure

. –
. –
?H-

NaBH4 .1

LiAlH4 .2

. ' –
: ,

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. – . 2 – 108 Figure

8.6.16
:)Schiff base(

:) (

. - 109 Figure

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, 110 Figure

. – . " –
( – . -
. ' .) –
. . " –

.) (

–
.) ( 2

.
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.

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–
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) (
. .sp3

\ 111 Figure

2- 112 Figure

. –

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. –) ( – Keto-enol tautomerism
.enol keto .

:
-

keto ,enol –
.

:
-

. OH- 113 Figure

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. : - , - 114 Figure

: \

. – 2 115 Figure
.

: \
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.

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. ,

. ) ( –

13.6.16
.)ambident(

,
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: .
. ,
:) (

, ? 116 Figure
.

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, . , ,
. , ,
:
(
.THF LDA .)

:SN2

Aldol addition

.
. \ \
. .

. 117 Figure

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. – *
, .
.aldol condensation

. – ,) (
( C-C
.)

. 118 Figure

.)enone(

. , –

-
.
. –
. –
.
:
X-C ,N-C ,O-C ' CH '

.CO\CN\CX CH '

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15.6.16
:

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. H2 .
:
. H2 – -
. 2- 2 -
.H++H- – -

. ,) (
: :NaBH4 LiAlH4 ,

:NaBH4 LiAlH4

. B Al
. ,
.) NaBH4 ( LiAlH4 ,

. NaBH4 –

2, ' , .
.
H2CrO4 "

: \ .Na2Cr2O7+H2SO4

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. , -

. ' )NH3( –
. ,
: , ' ,

.
.

. " " – PKa

. .
.) ( 5
,)36 pka ( NH2- –
: \ .

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.)LiAlH4( –

Cn(H2O)n .OH

:
. – -
. – -

. ,
. +

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2- ( , .
. )
.
. 2
. 3-10
. 10
S R , .
.L D

.L ,D . OH

.D

: –

3 2 D 119 Figure

:) ( ,

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.
: –

:
5-6 , . 2 2- .
:

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OH . )0.02%( 120 Figure

. –

. OH " –
.
. ,
, ( –
.) – "
.2 ' 1' *
.)pyranoses( –

.)furanoses(

.
?
. =
. =
.) ( 90
.
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. L D .

.109.5 .
.

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. ,109.5 ,
. 4.
, eclipsed
.

: .
111 – -

.) 3 3–6 " (
.6 " –
. –

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20.6.16
. 2 , ,
, , ,
, – .
.
( 2 –
)

Ring flip - 121 Figure

. -
: –

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. 122 Figure

. –
.
,
twist boat .eclipsed
.eclipsed

, " "
.

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: anti ,

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- .cis = - - 123 Figure

) ( .trans =

. - 124 Figure
. " "

.
. ,

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, 125 Figure

. .
.
.
.) 30-40 60 ( 1:3 ,
,)R H ( , .
:

,sp3 –
.
.
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.) ( ,
. \ \

22.6.16
: –
. .
. – .

. = . =
.D L . 2 ,
.)! D ( L

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D L126 Figure

H N( S L
.)
, , ( . 20
.) ,
. - \
. . "
.R .R , , :

. H=R . . –

. .R=CH3 –

. .R=Isopropyl –

–
. . –
. –
, 2 . –
. .
( OH . – , ,
.)
(
nm220 .)uv ( nm280 .)
.

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. .R=CH3OH –

. R –

.) ( OH –

– . . –
. – .
( 2 .SH – –
. .)
. pH . – , ,

3 .
.)PKa=12.5( .

.) 2 ( –
. ) ( , pH PKa .
.
( – ,
.) –

( ' 2
.)
. – 2 – zwitterion

pH .isoelectric point – pi 0
.0

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. . ' 3 – –

.1 + .+2 127 Figure

.1 - .0 ..
.)PI ( pka 2 '

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27.6.16
. PKa

.' ,' , : ,
. .
.) (
. "
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, . -
.
: –
. -
. -
. -
. –) ( -

,
.
.trans cis ,

. trans

. cis . ,
. trans cis

.) (
. . 4 – -
. – phi

psi

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. , , –

. – –
3 . –
( loop regions – , :
.)
– Ramachandran plot
: .

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alpha helix

.left handed, right handed –

:

3.6 .
. i+4 i

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, ,
. ,
.
. –
beta strand and beta sheet

. –
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.) - (

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.) ( –

. .
) ( . – – unfolding
.)Guanidinium chloride Urea ' (

.
,
.
?
– –
.) (
:

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. ' pH ,

beta- : . –
) ( .Mercaptoethanol

. . –
.
.
Urea .Christian Anfinsen
.
. , .
.

: – Levinthal paradox

.) (" " 2n – n

.10n 32n 3

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1087 100 , .1013

. –
. –
.

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