,-[KA].IES1. Draw stmcflral formula for:

a) 2-methylpropaneI

-*r t t

^C-C_C-li t

d) 1,3-di*Ylyclohexane

+./- \

-c. c:' r I-C C'- .1

' \ c / : -g) 3,3-diethyftEntane

-e'IoQ-

I t t t t-c-c-c-c-c_-

1ll !t

C)€rt E,a^Q.I

b) z,z-dimethylbutane

e) 3.ethylpentane

h) 2,3-dichlorobutane

I

-c-'t , [ |

| I I

-c-c-c -c -+*c"c-;r l \ r i l -c- - a-tt

-<-- 'I

I-c-tl l t

-C - C- C-C-ll l l

-L--I

I*c- I-c*

r1l f t

_C - C-Q-C- C-lt t l l

-e-I

l l l l r-c -e- c-C^-c-

t ' l I I r-C-t-Q.

I

rqt t r*Q,-C-C- 'C- 'i l i r r

I

-C-l l r-c-c-c-

tl l

-c-

1lc - 'L*r. I

l t l

' C - 'c : g-I r r

-C--t

-€' -I

Z.Draw and name the 3 isomers of C5H12.

l l' /^-? -_vV

, l r- e-'

tl

O - ,nr{fi.1l t*t""c-

Prnc) 4-ethyl-3,3 -dimethylheptane

8 2,3,5-trimethylhexane

tl l l t r-e- - C*C- O-C/-C-. '. t t g t | |

-C-t

k) 3 -bromo-5-methylheptane

Brtl l t-c . -c-c-c

Ir l l

v'nrte-b,p, aA ryf.t -fufsrafb

a,i Je*\br'r*3. Which compound has the higher melting point: propane or pentane? Explain.

P.,' t ,& l,^^ J)* 4l* n&Iin1 p".,rt, As yt* t*C ^^& H 's , i*, h." ftvfe e-s ..o-Tfu f LD t&ra o*J .t

4. Mrat is the equation for the complete combustion of pentane? T 35 ^ * Ma;4Lr\' :

ru- -y'n dr-q!. ..&a,e.

CsA,, + AOa ;) 5C.oa + 6L{aO

5. Give an exarnple of u.ru.O*g of an alkane.I

C,o H , , + He c-o-2, C* H,o + Ct f i , ,

6. Give the equation of the reaction of bromine with ethane.

- r r + [ \ r^ -5-\q** ( .* . ,F1*B,r t nt-LaHA - - 'A ; " -3r t5

L7. Name the following:

a) CHr CH:r l l

CHr-CH-CHz-C -CH:ICHr

d) cH3 - cHz'- cH - cI{ - cHu - cH)- cH:l l

CHr CHz - CHr

e) ClI

cHr - cH - cH - cH.- cE- cHrItcrCHr

CII

CHr - C- CHz- CHz-CHrICHr

g) CHr CHr Brt l r f

cH:- c-cH-c-c-cH:lHlCH: I

b)CH3-CHz-CH-CH-CHz-CHz-CH: 1,4 ^ l -^4/ . t t I| | Q,'t abert4UoPfu', i2

CHr - CHz CH2- CHr U I

3 r"r+l { '4 i?

;J\ -Fta-e_s.

tt tJ I r . l I i , '1- e- .11,4t- 3- neiLyt l , f tar ,e

3 -okl*o - e-*eqL(,*"*r*

e - &bru*a- n1"{i+*La,ts

4 - ko,no 5 - iocl o - a, &, 3 - *; "*+l'JU*t*

h) cH: - cHz cll1

CH:-CH-C-CHz-Cl l r lCHI CH:

HI

- c - cHz-cHrI

CI5,L- A,,).,[oro- 3- "+t t- A,3 -J,h"{4LacLaru

F

AIKENES

1. Draw structural formula for the following:

3 -chloro-4-methyl- 1 -P entene

tt.4-f

-f- t vv

c) trans-3,4-dibromo-5,5,6-trichloro-3-octene

Br Ct C!Ir t r t l t

-6_C-C=C-C-C-G-C-tl t t f l l

Bc cl

e) 2,5-dimethyl-3-hexene

-c-1l-a--c--It

g) 2,3,5,6-tetrame thyl-2,5 -octad i enel!

-C- -C-'- / r l l l l

- .C-C=C-e-C=C-C

b) 4- chlo r o -2,2- dtmethyl-3 -hepteneI

-C- Ct

d) 2-methyl-2-butene

D I,2,3 -tri methylcyc loprop ene?-

-v

b, / \

- . j / \ . \

;^*C --- f t' |

-*-co

h) 6-bromo-2-chloro- 1,3,5-heptatriene

el Br\t l11t

-C =C-L=(.-{-=e-

llrc c-c-rt l

f-\J

I

t r1\ ! l t

-C-C-C=C-C-C-C-Itr l r

-c-I

I_c-rl l '*L-C=C-C-ll

t l r lC =C - e-C-

ll-C-

t

I-a-I

tC_

t,l l l

-c-I1 l

- C--t

2. Draw and name the geometric isomers of C2H2CIZ.t { i ll rC=Cfl

cl el

c luttc3cItHCI

uA - l, J d;ul,{aco -li,r""*

*n*- t, d) - rt;-hloro.,!**3. What is the equation for the complete combustion of 2-pentene?

A CsA,o + 15 Oa -) to c-o d + lo t lbo

4. Give the equation of the reaction of bromine with 2-hexene.

- Give the equation of the reaction of watet with propene.

cat_+

lrl l l l^c-c--c-a-c-c- +\rtr

-L=t--L- + Hao

{os LRtn

lr\tnI.C C_C C-C.C-

tl\1r\

Br Br

Oti1t \ .-e-c-c-t1\

3 -rn"q+,"w

d) CHzt l

CHr -CHz - C - CHz- CHz- CHr

e) ClI

cHr-cH-cH-CH:CH-CHrI

.*--, CHI

0 CHz- CHrI

CHr-C-CHz-CH:CHzICHr

6. irlame the following:

a)CH:-C=CHzICH3

b) Br CH3\/

\!

C=C/

/\CHr Br

c) CHr - CHz - CH: CH -CHz - CH3 3 - A.r* el\A

&^"+!,XL- f - wt*

4, 4' "l;rt'-+l6L - I - L"* ut@-

g) CHiCHT Br | , , t | \ || | | { ro^o -3-Ero. . -A- iodo-+,5,5 -)r ; "** lqL-J- lsxea

cH:- c-cH -c:c-cH3 dt lCHr I

h) cHr - cH2 cll l

CHr- CH- C - CHz- C : C- CHz-CHrt l l\--'' cHr clr3

+: J,4 - );"1" lo"o - c - "l.lrl- t",t -"I;^rl+t J orh^

7L-

ALKYNES

1. Draw strrctural formula for the following:

) 3 -chloro-4-rnethYl- 1 -PenlPne

r l\ - ' r I-C=C-C ' ' ' t - -

i ; i- t -c) 5,5-dimethYl-2-hexYne

b),

1

t

5 - chloro -2,2- dimethyl- 3 -heptyne\

-C. CIlr l l

-c-c7c-c-L*C-.!t

-c-t

l f r r r

-C;@-caC--C-c-c--lr l \ t

l-C-

l l r t-c-c ?c -c-c-9-

it t l-c-

I

d) 5-ethyl-3-hepfyne ) **E

I

-C-

f) 2,2,5,5-tetramethyl- 3 -hexynee) 2-butyne

I

'C *CI

I=C.*c-I

I. -c-.l t

-C-C-r l -c-I

I

- f - 'I

c2 c-c - L-rl

- ? 'nI

? C-

g) t, 1 -dichloro-3,5-octadiYne

e\t_c-t

crC-C; C-L-L-

ll

h) 1,3,5-heptatriyne

t4= C- C=C* C;C-C-

T

t

Ca-C=I

2. Draw and name the isomers of C4H5CI-

1{- C zC-C\ Ct -C*c- C7C-

I-c-I

Ic=c-c-cl,|l

t l

-C-e.-Cll

c t

| -"1,,1*r-A-b!r l .

3 - &.,1^o -l^ b.-ty,""

It-c-c-

gl

3. What is the equation for the complete combustion of propyne?

l- J,ic'.o - l- L\"c

Cs ilt

4. Give the equation of the reaction of hydrogen chloride with 2-hexyne.

t l t ! -Y-L^L=.-L-a-L- | F\C\ ->lr\1

r f

4- JIrro - l-h*+1*

loa -) 3co^ -{ ' a i iec

rc,t \ t \-c :Q-9-?-?"6{*-

r ! \

- (=C-c'L 'C*It\r \

C\

t-t

b) cH3I

CH = C-C-CH3I

CH:

C) CH:I

CHr-C=C-CH-CH3

d) CHz- CH:I

CH:-CH:-CH-C:C-CH:

e) clI

CHr - CH - CH - C: C-CHIICHr

0 cHz- cH:I

CH: - C-CHz-CHz-C=CHICH:

g) CHI CH:l l

CH:- C- CH -C=C-IICH:

5. r'{ame the following:

a) CH3-C = C-CH-CH -CH3

+ -^'qf e prrrLrJ,,*

q JI*o-s- *hL- p - t**{^s_

5,5 e;*+\ f - l_bptg*

l- iola - g,I ,4 -1t; ,*\L l_ p*,h,*

h) CHr -CHzI

clt- cn- c - cH2_ c= c _ cl{z_cH:I IcH3 cr{3 6-rr l , \L_6,+ _d.,^.+lr(_:_ ootr*du

Ms. Tanner, Ms. RidgeSCH 4U1

Comparing Organic ComPounds

'/ l-pentanol (B.P. 411 K)

,/ 2-methyl-2-butanol (B-P. 375 K)

'/ Ethoxypropane (B.P. 337 K)

'/ 2-pentanone (B-P- 375 K)

,/ pentanal (8.P. 376 K)

w the followine 7 moleculeslowest boiling point. Explain your reasonmg:

,/ 1-hexanol

,/ ethoxy-2-methyl-propane

,/ hexanoic acid

,/ 3-hexanone

,/ propyl propanoate

./ hexane

,/ 3-aminohexane

of hi

SCH 4U1, Ms. Tanner, Ms. Ridge

Ah[swERS Tq WORKSTTEET - COMPARING ORGANTC QOMPOT]NpS

Draw the 5 molecules and place them in order of highest boiling point to lowest boilingpoint.

Hrc

2\

CH: CH:

OHIIIHsc-q-cl-l

*=t ., '/"L.dcH:

H:c /cH\.r,f'*\*rPo

H=c/c Hzr

o,/"t-. r,f cH r

SCH 4TJI

nrrlt\.f,t\.f,\,

H,c/*\{'\.*-*\n

Hucftt\.rfo-#

Ms. Tanner, Ms. Ridge

Boiling point = 477 K

Boiling point:430 K

Boiling poinr = 396 K

Boiling point = 396 K

Boiling poinr: 3gg K

Boiling point: 354 K

n'J-o,

H*/tn\.--t\. ,,/cH3

ilo

HrN/t\.rft\ ,{'\.n

Hrc/tt\o

L,,*r1t\r{t\{* Boiling point :342K

'r JH 4U1 Organic Chemistry Ms. Tanner, Mrs. Ridge

Organic Reactions Worksheet

Note - Use HCl, HzO, O* (KMnOa), NH3, and Cl2 when necessary

1. Using an alkene, produce 2-butanone

1-butene * Water ) 2-butanol + O* ) 2-butanone

2. Using two alcohols, produce methyt butanoate

1-butanol + O* ) butanal + g* ) butanoic acid

methanol + butanoic acid ) methyl butanoate * HzO

3. Using an alkane and an carboxylic acid, produce N-ethyl butanamide

ethane+Clz ) l-chloroethane+NHg ) ethylamine

butanoic acid + ethylamine ) N-ethyl butanamide

4. using an alkane and an alkene, produce methoxyethane

methane + Clz ) l-chloromethane * HzO ) methanol

ethene+HzO)ethanol{1"1;'6r;t t-ua1

ethanol* ethanol ) rnethoxyethane o dr_o

5. Using an alcohol and an alkyl halide, produce ethyl propanoate

l-chloroethane + HzO ) ethanol

1-propanol + 6r' ) propanal + O* ) propanoic acid

ethanol * propanoic acid ) ethyl propanoate * HzO

6. Using an alcohol, produce an aminoethane

ethanol(HzSo+catalyst)) f f ig)ethene+HCl)1-chloroethane+NH:) aminoethane

7. Using an alkene, produce 2-pentanone

l-pentene + HzO ) 2-pentanol + O* ) 2-pentanone

T asf rrnr lafed hrr R Tcnner nn 1 ? 11) nOO\

'nro€

(}q:

-L

f,{

o.Tl

of,ozEc)Trnc){

(Jz$

+-t-

ni- +*{.', aJ

Y' L}

,tlrIi

ril

F], l:"f

f/\Fr

i 'T-!

i )

at-D

q !d\o 3;_F edf, =o*il =t

oo igs=_ r_*- ' -

oo9qg

i-r-a.

+>nQVj:: f3, t>

(L trt) t \ -

. : \g? -1. . i -

--->

?tcl

I; i *,l/A.i f r . t o

.*

n

f' {-ZI

;X

-r-'1.--

L,. '?*

Y;- .

' ' . { '-r

')