6
uuu?nfn nr*iaugnerafi 1. c{ufia{qmatnelnhlulurrr.rqaniTornrtfuvi?tiriahld ?riar'r(uan4rptr'rmqn Ltu)rgq '- $ c[r,ulJ't cr uu ]n r 13-{ 1) cH,cHclcq 2) (cq),CHoH sl crrpHpH=CHCI 4) (CH.),C=c(Cq)c= CCH3 I 1) pentane 2) chlorobutane 3) pentanol dd nrriruundl?€uflfa e. u{r{.rri{utalc','lflhynaurialldfiaovlr ar:rudrfi {nrflunrfiuvrftirl'*r'o1^ z. 6.rr6uvr?6uiahlfr flotr[ra5lnna]rlfi uuu ql udnrtnnnhrfi rf, ulrjlfirft uun 1) cqcH2cHrocH3 ?'. 2\ Cft-CH-CH2CHO cH3cH2c= ccH3 O CHr *o-8-"","*r-ln-"r. *. *rr6uYrftftnfirflu{o s {arflu t ) nrnjrgnauirlfi'l (saturated compounds) 2) nrtjtYnoulatetarfiLou 3) unsaturatednon-hYdrocarbon s. qtrfiflutnnahuarar#fiuqiftrffur{alrlduradrmv z tfin d6 ia r) fitnufiiinrfriau 5otnox 2) r'uar'rudfio.fiiau s oynail *-.ja e) ralrrffiij + arfi-rau edt .i a) d'n61adfr rflua;ttlrfin sl c{r#fi1i"l6tnuunvtontvrai fifinrfuau 5 ovtlou e. ctfinuluarurrf, E{atrif, fiu{ft r{d'ua;te.riT'r CHpHTCH=CH. o ""r-$-"*2cH2ctfu o ,-$-o"* HO 8) 4) 1l ,l lac 2) a^Y^ )

3,+ - Chiang Mai University. n1fimu&da;oynoillu{o 12 finrr{pr hybridisation uulln 14. cmmrudn:{dattld fi'unvdriruurn{uny'[nfin,:trrflurir4rn.jrri'u *nrfrT fii,r ezfififlrr.:rotnnrr.rfiriruflu

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uuu?nfn

nr*iaugnerafi

1. c{ufia{qmatnelnhlulurrr.rqaniTornrtfuvi?tiriahld ?riar'r(uan4rptr'rmqn

Ltu)rgq '- $ c[r,ulJ't cr uu ]n r 13-{

1) cH,cHclcq 2) (cq),CHoH sl crrpHpH=CHCI 4) (CH.),C=c(Cq)c= CCH3

I

1) pentane 2) chlorobutane 3) pentanol

ddnrriruundl?€uflfa

e. u{r{.rri{utalc','lflhynaurialldfiaovlr ar:rudrfi {nrflunrfiuvrftirl'*r'o1^

z. 6.rr6uvr?6uiahlfr flotr[ra5lnna]rlfi uuu ql udnrtnnnhrfi rf, ulrjlfirft uun

1) cqcH2cHrocH3

?'.2\ Cft-CH-CH2CHO

cH3cH2c= ccH3

O CHr

*o-8-"","*r-ln-"r.

*. *rr6uYrftftnfirflu{o s {arflu

t ) nrnjrgnauirlfi'l (saturated compounds)

2) nrtjtYnoulatetarfiLou

3) unsaturatednon-hYdrocarbon

s. qtrfiflutnnahuarar#fiuqiftrffur{alrlduradrmv z tfind6 iar) fitnufiiinrfriau 5otnox

2) r'uar'rudfio.fiiau s oynail*-.jae) ralrrffiij + arfi-rau

edt .ia) d'n61adfr rflua;ttlrfin

sl c{r#fi1i"l6tnuunvtontvrai fifinrfuau 5 ovtlou

e. ctfinuluarurrf, E{atrif, fiu{ft r{d'ua;te.riT'r

CHpHTCH=CH.

o

""r-$-"*2cH2ctfu

o

,-$-o"*

HO

8)4)

1l

,l

lac

2) a^Y^)

3,+ 4)HH\J/-\

cH3c@(cHr{o cH2c}13

rn*irrderr*n#i

z. eltitrda R pAC torctr?Euyfi{riotjf,

t, qtcll2-cH:cHz

3) CH3(CH2LCH2OH

OHI

5) CH9(CFL)3CH-CH3

9H,I

7} CH'T-CH2CH3

OH

rgr +*

./ 13) Cq9HCH2N(CH2CH3)2IBrO

il15) CH3(CI-L)sC-H

cH" olll

17) CqGH2CHCH2qHCH'C-H

o ln,I19) Q5r=61-16HrC-|l

oI21) CH3CH2CCH2CH3

23) Ct(CHr)5COOH

OHt

25t CqCH-CO2H

oIH"N-Ct-lcH"C-H-l

cH^ otilHC=C4}FCCH^

.l o

lfl-t

/^1 I ) cH3-?t+?H-?H-cH?cH3

Br Br OH

z) cxs-?H-c=c-cH3clt?

4) Ctl3tH€H=CHz

OH

/et cHucrqTH-c=ccrloH .

ct-tcH3

/a) cH.-o-cFlcuct-t

10) cH3-cH-cHr-o-cH3

CH.

12) CH3(CHr5l'llt

cl|"CH.CHCH""'tO NH"il

H-CCHpHTCH3

14)

16)

CII

27)

18) cr-L?HCHcHo

BrOll

20) CH3CHCH2CCH2CHzCH3"lCH^ O' ll

BT.CCHTCHTCCBT.

GBT"CHTCHTCOTH

oll

H€-gH-CH2COTHI

cl

H2N€H2C=CCH2COr|{

ooIltCI!CH=Ci|CH€-CHs{,H

IcH?clt

2e)

28)

bc

1G1

' n- riS. unnl6ntln?{651{14'lr{1tiltynCIumo

luu

1) 2-iodo-2-methYlProPane

3) 2,3-dimethYl-2-butene

5) cis-3-hexene uav frans-3-hexene

7) 1,'l -dichloro-3-methYlhexane

9) 2-methYl-3-hexYne

1 1 ) 1, 1, 1 -trifl uoro-4-(2-methylpropyl) nonane

2) 2,4,4-trimethYl-1 -Pentene'6

4) 2-methyl-1'4-hexadiene,

6) isopropylbromide

8) 4{1, 1 -dimethylethYl)hePtane

1 0) 2-chloro-1 -fl uoro- 1 -butene

1 2) 3-methYl-2pentanol

14) isoPentylalcohot

1 6) 3-methYl-3-hexen-2-amine

18) N-ethYlhepanamrne

20) 3-Penten-2'one

22) 4-chloro-2-Pentenal

24) 3-methYlbutanoic acid

26) 5-bromo-3'he4Ynoic acid ,

28) 4-oxopentanoic acid

30) sodium trifluoroacetate

2) 1,1-dichlor+'$hexanbl

4) 3-ethYt-2-butanot

6) 4-bromo-1 -methYlPentanol

8) 2-hYdroXYProPanamine

g.*orElr,iohrfirriqnfim hiriautnerflhrra$r.ufifiafinfr unzr?sniohlqnfior 1'r4'in{afi1fi6'rfinl

1 3) 3-bromo-4-chloro-5-isopropyl-5-methyloctane

15) ethytProPYlamine

1 7) N,N-dimethYtbutanamine

19) 3-heptanone

21) ethYl isoProPYl ketone

23) 3-bromo-$methYloctanal

25) 4-amino-2-Pentenal

27) 5-hYdroXY-2-hexanonq

29) Potassium hexanoate

1) 1,1-dimethYlPentane

3) $ethfl-4-methYlhexane

5) &methYl-2-ProPYlhexane

7) 4,4-dimethYl-3-ethYlPentane

10. rfiNqn?tn?{fih{ra{s{1apna:.rsiahlf, rnrlarli'luttn{t;nto{ hybridisation

1) CH.=C(CH,)' 2) Cu'=61-16H=CHz 3) CH= CCH'zCH3

fiu m ua;ta t'r a Frs1l ra qatala r:6 unE€

1 1 . nttrNgildr.rtiltaqn flulA{c{rxfi 0 ta{tr1

nrfiiauusioraYnox

1) cHpcq 2) cH2O 3)

ro.:n1iuaulnorneil

4)onknaufiriruuati rtrHnr'rfi'rrrqtfinlo{ hybridisatio' n llrH

co, 4) CH3CN 5) CH'CH=CHCH,

t z. rlur{uo#fitaun nmfi r{'liltt:nruwirlna-*eq*#-"*,/"f"

bb

6) CHr=C=CH,

13. n1fimu&da;oynoillu{o 12 finrr{pr hybridisation uulln

14. cmmrudn:{dattld fi'unvdriruurn{uny'[nfin,:trrflurir4rn.jrri'u *nrfrT fii,r ezfififlrr.:rotnnrr.rfiriruflu

odtb1) CHICI riu Cl-cl

2) CH3OH riu (CH3),Si

ts. runlnlaTnarqudtntri'uoonf rsuso.rnrnovdfin 6rfinmurflunanatn.ir1atnrnqudrnrrrirrrrfuaut

t o. oGursaru umnrirrrorlnrdo nro.r,6'arnwarTndnrnru"[uurinr{o

1) CH4 bp. -164 "C CH3CH3

2) CH3CH2CH2CH2CH2CH3 bP. 69 OC

CH3CH(CH3)CH(CHJCI3

3) cBr, bp. 190 oC ccl4 bp. 77

oc cHo bp. -164 oC

,t z. aT ruoin;(riotrlfi nrr'[nrfi 1 o rdo na.r n.jr riu rn r rru ry'lor

cH3ocH3 ttay cH3cH2oH

cH3cH2cH2oH ltnr HOCH2CH2OH

1)

2)

18. rflnrrxrrln nmilrynou6roafii'Qhlfrsardanfrrn.jT dnnoaodfifirurntrmnn'[ndrdt.:ri'u #.rrfifinrmr.rarxr:nrqrl

tuntnvn'i erfi rtn fi rdsr rTu

-..Ad4d4r,xrdru19. [lruutyruulnLqonlo.i[ouuuay/uro6'rrilrrnoLFlo LlJu y{toNy}.10fiu1fltlrFlrJn

zz. e.:tfiflulnt{fiiNro{fi1e u?0fr'rnnx (intermediate) drfinrqrnnmunnrfuoydritaunrlurJfrffimeioh]d

2)

3) H-Ct rTu H-CH3

4) H3c-Li rYu Li-oH

bp. -89oC

bp. 58 oC

3) CH3CHTCOOH rav C4COOCH3

4) CH3COCH3 unr CH3CH?CHzOH

1) methanamine, propanamine, heptanamine, decanamine

2) ethanamine, ethanol, propane

3) propylamine, ethylmethylamine, trimethylamine

dou

ZO. 64.:drd'urr11l61u1?n'[unrraynmrirEos pentane, ethoxyethane rror butanol

.....tAG O dA 4l

u0n6s'r [urnrJauilSEt

2 t . unnrnrtfi o intermediate q1 n nlr ilFl nrolri'uoyfi d'ruun

1) radical s'ln homolytic cleavage lo.i cH3cHz---H

2) carbocation q1n heterolytic cleavage flo.i (CH,)rC--Br

3) carbanion s1n heterolytic cleavage 110.i CH,--MgCl

H2C-|-CHI _+(\/{.* Hlo-sorH,

IEsr,

3) cH3cH2rtr 4

\ \-A -C=N

o\t?4\ f,$c-cH.*1oo*

za. rJfrffiuroiotilfiA'nrflu rJfrffiurn.uifir (addition) rJflffiurnrrirvrufi (substitution) rJf,fi?tnnr*ir{pr

(elimination) uiorlfl ffiarnra{n6fl '0d'r"luil (reanangement)

1) CH.CHTBT + NaCN CH3CH2CN + NaBr

+ o2N-NO2 ---------'----*2)

3)

4)

OH

+ H2SOa+ H2O

cH3cH3

cH3cooH

cH3cH3

c6H5NH2

cH3cHoHCH2OH

2 CH3CH2OH

o'CH.-C-O + CH3CHaOH

oo

o.A-- .0I\24. n1rutfi fl un:lnuarnt6uvritioiotrld tfi nnrnrlfl ffiaraonB rori'uuloid'n{'u

1) cH.cHrBr

2\ CHpHTOH --------f

3) CHr=i611,

4) c6H5No2

5) CFI.CH=CH,

6) CH3COOCH2CI ----:--)

zs. 3rs rquffi lfiturJflffi a r sialdfl fr t,|rirfi tfl ufi r ndlaldd u?o 6 6nlm ild d

1)

2)

3)

CH3CI + AlCl3

ROH + H*

'C(Cq)3 + Cl-

oil

4l CH3-C-OCH2CH, + 911-

_-}

-----------+

--------------+

-------------)

*cH, + ct-Atctr-

RO*H2

(cH3)3c-cl

hJfi n'l*fiufrcndlatr,ld #o Edntsrrlyld

------------*f

--------------)

---.-|

-

cH.cHrocH. r

cH3cH2CH-CH3

osqH

CH3CH2CHBT-CHrBr

CH3CH2CH2N'H. Br-

Nal

Sll"CHrCH=CH,

cH.cHrcHrBr

CH.Br rTu Nu:

''y) cH.ruH, ntu E.

': 'l:,';rli

[r uuil,:satnr efi nrlfr ffi ur?ru.i1{Iil m q nudnrTuiro nurifi fi ruun

J zycnron fiu H.

,6)C,t-t3O-H, fiu Nu:

13) Cl-lr=CH, titt H.

/a) nrc=a flu Nu:

b6d. '