10
5 IUPAC5@ &" <?= " <$@= " <?= 5$ > <'=;(")?(")2!09+ >$6*7$.%,#+$-8-:/1#<$=6349+ alkane (>&:9.)A=*@ane alkene (C=C)A=*@ene <-C=C%(#a+-@ene ;84"!84" 7&/) alkyne (CC)A=*@yne <-CC%(#a+-@yne ;84"!84" 7&/) C=CCC0#(#ene+yne ;C=C84") 84"+ 16- =* meth eth prop but pent hex hept oct non dec - ;5 - ;5 1 mono 4 tetra 2 di 5 penta 3 tri 6 hexa - ;5 - ;5 2 bis 4 tetrakis 3 tris 5 pentakis octa-2,5-diene × octa-3,6-diene oct-1-ene-7-yne × oct-7-ene-1-yne ; -;2 ; -;2 ? ?-;23$8,'< -(#3 3 bis(trifuloromethyl) × bis(methyl)

5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

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Page 1: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

�����5���IUPAC���5���@ ��� �&"

<�?��=

" <�$@���=

��"<�?� =

���5�$><�'�=;(" )?(��")2!�09+>�$6*�7��$.%,#�+�$-8��-:/1#�<�$=6��349+

alkane (>&:9.)A=*@anealkene (C=C)A=*@ene<-�C=C�%�(#��a+ �-@ene�;� ��84"��!����84"�� �7&�/�)���������

alkyne (C≡C)A=*@yne<-�C≡C�%�(#��a+ �-@yne�;� ��84"��!����84"�� �7&�/�)���������

C=C���C≡C�0#��(#�ene+yne�;�C=C��84"�)�������84"� �+��

16- � � � � � � � ��

=* meth eth prop but pent hex hept oct non dec

- ;5 - ;5

1 mono 4 tetra

2 di 5 penta

3 tri 6 hexa

�- ;5 �- ;5

2 bis 4 tetrakis3 tris 5 pentakis

○ octa-2,5-diene × octa-3,6-diene

○ oct-1-ene-7-yne × oct-7-ene-1-yne

;���-�;2

;����-�;2?

?-;2�3��$�8,'�<-��(#����3����3� ○ bis(trifuloromethyl)

× bis(methyl)

Page 2: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

��������(1-1)○� ��������)�����)S���**� �,$��#�!���)�*) �%����(���*���,�$�� �������!���

�' ��� � �)��"* ���)�&"* �%�

alkane - "�+ane "�+ylalkene - "�+ene "�+enyl

alkyne - "�+yne "�+ynyl

imine =NH "�+an+imine imino+"�+� �

amine -NH2 "�+an+amine amino+"�+� �

thiol -SH "�+an+thiol sulfanyl+"�+� �

alcohol/phenol -OH "�+an+ol hydroxy+"�+� �

ketone -(C=O)- "�+an+one oxo+"�+� �

nitrile -C≡N "�+ane+nitrile cyano+"�+� �

aldehyde -CHO "�+an+al formyl+"�+� �

amide -CONH2 "�+an+amide carbamoyl+"�+� �

acyl halide -COX "�+an+oyl halide haloformyl+"�+� �

ester -COOR R "�+an+oate R�"�+oxycarbonyl+"�+� �

carboxlic acid -COOH "�+an+oic acid carboxy+"�+� �

Page 3: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

��������(1-2)�������������������

�� � ���

fluoride -F fluoro������� 2,2,2-trifluoroethan-1-ol

chloride -Cl chloro������� 1-chlorobutane

bromide -Br bromo������� 1-bromo-2-chloroethane

iodide -I iodo������� iodomethane

azide -N3 azido������� 1-azidepropane

diazo =N2 diazo������� diazomethane

nitorosyl -NO nitroso������� 1-nitrosopropane

nitoro -NO2 nitoro������� nitromethane

alkoxy -OR R����oxy������� chloro(methoxy)methane

thioalkoxy -SR R����yl�thio������� 2-methylthiopropane

F3C OH

Cl

BrCl

H3C IN3

H2C N2NO

H3C NO2

H3CO Cl

SH3C

Page 4: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

�������� (1-3)○F8-+>WS-+>X�<5WIUPAC?6XYX"P�=3>

a: "/W%&Q$�:�V�2H/X�:�0,�Pb: !T.D*W0OD*X�:�0,�Pc: U;@C(19�:�0��Pd: #OD*�:0�Pe: "/����!T.D*�$FA)�:�4��Pf: 7RMWF8/X�9�:0�$FA)�4��P

ZXJLa: 7RM�QA��F8/+�� �����Q�KN������di, tri���9�B�IK�S�� G���

b: :'�KN��F8/�9�0�������c: :'�KN��F8/�$FA)��E.�:4���������

4-bromo-1,1,1-trifluorobutane 4,4,4-trifluoro-3-methyl-2-(trifluoromethyl)butan-1-ol

%&Q$[-C=C- > -C≡C- > -C-C-

12

3

675

43

21

4-propylhepta-1,5-diene

12

36

7

1

23

5

432

1

4-(prop-2-yn-1-yl)-4-propylhepta-1,5-diene

32

16

7

1

23

5

412

3 OH

%&Q$[-OH > -C=C- > -C≡C-4-(prop-2-en-1-yl)-4-(prop-2-yn-1-yl)

hept-5-en-1-ol

32

1

4F3C OH

CF3

CH3

32

1

4F3C Br

�������������

Page 5: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

��������(2-1)○ $2��,8R��,9

S��,�.���� �/�(%5�-���$2 0��3��+';1) :$2 8� 9

1) �4*"�� !���������6�� �

07 �#& �� ��6�

azide -N3 1) :azide

iodide -I 1) :iodide

bromide -Br 1) :bromide

chloride -Cl 1) :chloride

fluoride -F 1) :fluoride

sulfide R1-S-R2 1) (R1)+1) (R2):sulfide

ether R1-O-R2 1) (R1)+1) (R2):ether

thiol -SH 1) :hydrosulfide

alcohol -OH 1) :alcohol

thioketone R1-(C=S)-R2 1) (R1)+1) (R2):thioketone

ketone R1-(C=O)-R2 1) (R1)+1) (R2):ketone

isonitrile -N≡C 1) :isonitrile

nitrile -C≡N 1) :nitrile

[S��,]chloro(methoxy)methane [R��,]Chloromethyl methyl ether

[S��,]4-methylpentan-2-one [R��,]methyl 2-methylpropyl ketone

O Cl

O

Page 6: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

��������(2-2)○ ����������

[S��]2-propyl[R��]1-methylethyl[ �]isopropyl

[S��]2-butyl[R��]1-methylpropyl[ �]sec-butyl

[S/R��]2-methylpropyl[ �]isobutyl

[S/R��]1,1-dimethylethyl[ �]tert-butyl

[S/R��]3-methylbutyl[ �]isopentyl

[S/R��]2,2-dimethylpropyl[ �]neopentyl

[S/R��]1,1-dimethylpropyl[ �]tert-pentyl

[S/R��]ethenyl[ �]vinyl

[S/R��]2-propenyl[ �]allyl

[S/R��]ethanoyl[ �]acetyl

[S/R��]propanoyl[ �]propionyl

[S/R��]butanoyl[ �]butyryl

[S/R��]pentanoyl[ �]valeryl

[S/R��]propenoic[ �]acryloyl

[S/R��]2-methylpropenoic[ �]methacryloyl

[S/R��]trans-but-2-enoyl[ �]trans-crotonyl

���

O O O O

OOO

Page 7: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

��������(3-1)○C9,.B�20@";OK��� cyclo!��� cyclo + K8"&P3G.�H<4�#�����5.���)HD-!��:I����

methylcyclopropane 3-methylcyclobutene 1-ethyl-3-methylcyclopentane

"6C9,.Ba: 'C9,.B

1) ;OK��� bicyclo!��� bicyclo+[x.y.z]+K82) 2 *�?OAF!G�$��?�AF=!J����+ �E��3) )HD-�?O�#���7��M�?��ND�D-!���

7-methylbicyclo[4.3.0]nonane 6-methylbicyclo[3.2.1]oct-2-eneb: $C9,.B

1) ;OK��� tricyclo!��� tricyclo+[w.x.y.za,b]+K82) 6�AF�1� ����'C!L��'C9�/ ���)HD-!(��3) ��Q��?>�AF=����)HD-!%(�����

7-methyltricyclo[4.2.0.02,8]oct-3-ene

6 75

4

32 1

8

96

7

5 4

3

21

8

67

5

4

32

1

8

Page 8: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

PI P

. P U

1 2 1 2 9 43 7 5 4 6A 6C8 4

alkane ane

( )

methane ethane propane butane pentane hexane heptane octane nonane

mono tetra

di penta

tri ( hexa

U

amine -NH2 an amine amino

H3CNH2

methanamine 2-methylpropanamine

NH21

2

3HO

O

H NH2(S)-2-aminopropanoic acid

NH

NH

N1-ethyl-N3-methyl-1,3-propanediamine

Page 9: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

��������(3-2)c: "$&G=.2ETW��DK�)��G������.2EU

1) @RP��� spiro!��� spiro+[x.y]+P<2)*LI1�"$&/:�Q��9��;��G�B��,����

spiro[4.5]decan-7-old: %#&G.2ETNKG.2EUG!C?����%#&+K!M @RP�

���G�8��!M P<�MF ��

+K MJ +K MJ

O oxa S thia

N aza P phospha

G6AMJ

G6AMJ

(S5 S5 (S5 S5

3* irene irane 5 ole olane

4 ete etane 6 ine ane

M���%#&+K!J @RP M���G�8��!J P<

oxirane aziridine VN�!4�'6G�irine!-H ���01-oxa-2-phosphetane

1,4-dioxane 1,3,5-triazine%#&G.2E���7�����>H3�-H�O�� ����

furan pyrrole imidazole pyridine pyrimidine pyrazine pyrrolidine piperidine

67

5

43

21

8

9 10

HO

O HN

PHO

OO

N

N

N

O HN

N

HN N

N

N

N

N HN

HN

Page 10: 5 · 2019-10-30 · 3* irene irane 5 ole olane 4 ete etane 6 ine ane M %#&+K!J @RPM G 8 !J P< oxirane aziridine VN !4 '6G irine!-H 0 1-oxa-2-phosphetane 1,4-dioxane 1,3,5-triazine

dd i dr

i n e .

i i

O oxa S thia

N aza P phospha

i n

oxacyclopropane(oxirane)

furan pyrrole imidazole pyridine pyrimidine pyrazine pyrrolidine piperidine

O HN

N

HN N

N

N

N

N HN

HN

3* irene irane 5 ole olane

4 ete etane 6 ine ane

2 n

N ) ) ( ) ) ) ( (,) ( (,) ) (

d 1 .

oxacyclopropene(oxirene)

azacyclopropane(azirane, aziridine)

HN

azacycloprop-2-ene(1H-azirene, 1H-azirine)

O O

HN

O

oxacyclobutane(oxetane)

S S

thiacyclopropane(thiirane)

thiacyclopropene(thiirene)

O

oxacyclobutene(2H-oxete)

HN

azacyclobutane(azetane, 2-azetidine)

HN

Azacyclobut-2-ene(2H-azete, 2-azetine)

S

thiacyclobutane(thetane)S

thiacyclobut-2-ene(2H-thete)