Review for Exam I answers Part I




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Chemistry 1152

Review for Exam I — Answers – Part I


Hexane

1. CH3CH2CH2CH2CH2CH3


There are other possible answers for this question.
2. a. CH4 b. CH3CH2CH2CH3 c.

d.

3. No number is needed as there is only one possible position



for it. (The number 2 position.)

4. All combustion reactions give carbon dioxide and water (CO2 + H2O). If there is a deficiency of oxygen, CO or C could be formed instead.


5. Alkanes are non-polar organic compounds. Water is a polar compound. Since “Like Dissolves Like,” we would never have expected that the two should mix.

6. a. 2-bromo-3-ethyl-3-methylpentane

b. 3-methylhexane

c. 5-chloro-4-ethyl-2,3-dimethylheptane

d. 3,5-dimethyl-6-propyldecane

e. 3-bromo-1-chloro-2-iodopropane

f. 1-chloro-2,3-dimethylpentane

g. 3-ethyl-2,6-dimethylheptane

h. 2,3-dimethylhexane

i. 4-ethyl-5-methylnonane

j. 1,1-dichloropropane

7. (a) (b)


(c)


(d)

(e) (f) (g)

(h)

(i) (j)


8. CH2=CHCH3
9. (a) (b) (c)

(d) (e) (f)

(g) (h) (i)

(j)


10. a. 2,4-dimethyl-2-hexene

b. cyclohexene

c. chloroethene

d. 2-bromo-2,6,6-trimethyl-4-nonyne

e. 3-methyl-1-butene

f. 4-ethyl-3-methyl-3-heptene

g. 3-bromocyclopentene

h. 7-iodo-4-methyl-2-heptene

i. heptane

j. 2-methylbutane

k. cyclohexane

l. methylbenzene (toluene)

m. 2-ethyl-1,3-dimethylbenzene

n. bromomethane

o. 1,4-dichlorobenzene or p-dichlorobenzene

p. 3,5-dinitro-1-propylbenzene

q. methylcycloheptane

r. 3-methyl-1-butyne

s. 3-phenylhexane
11. Add Br2. If the red-brown color of the Br2 disappears immediately, the compound was the alkene, 2-butene. If the color remains, or lingers only to fade in the light, it was the alkane, butane.
λ

12. No, both would react in the same fashion.


13. CH3CH2CH3 + Cl2 CH3CH2CH2—Cl + HCl

Alkane substitution reactions require heat or ultraviolet light and produce a by-product.


CH2=CHCH3 + Cl2
Alkene addition reactions are immediate without a catalyst and there is no by-product.
14. a. 3-methyl-4-octene

b. cyclopentane

c. 2-pentene

d. 1-pentene


15. (a) (b) (c)

(d) (e)

16. (a) B. It has the longest carbon chain

(b) A & D and C, E

(c) E. Markovnikov’s rule does not apply.

(d)


17.

(a) + Br2

h

(b) + Cl2



(c) CH3CH3 + Cl2

Pt

(d) + H2



(e) + HCl No Reaction

(f) + O2 CO2 + H2O



Ni

(h) CH3CH=CH2 + H2 CH3CH2CH3

(i) + HBr

Pt

(j) + H2



(k) + HCl

(l) + Cl2

(m) CH3CH2CH2CH2CH2CH2CH3 + O2 CO2 + H2O



(n) + Cl2

Fe

(o) + Br2



(p) + HCl

Fe

(q) + H2SO4



(r) + H2SO4

(s) + KMnO4

h

(u) + Br2



(v) CH2=CHCH3 + HCl

  1. + Excess HBr

(y) + HCl No Reaction

(z) + O2 CO2 + H2O



(aa) CH3CH=CHCH3 + O3

(bb) CH3CH=CHCH2CH3 + O3 +



  1. + Excess HBr

(ee) CH3CH=CHCH2CH3 + HCl or

Chemistry 1152

Review for Exam I — Answers – Part II
1. a) 2,2-dimethyl-1-butanol

b) 2-ethyl-1-pentanol

c) ethyl methyl ether (common) or methoxyethane

d) 4-bromo-3methyl-1-butanol

e) 5-chloro-4-ethyl-6-methyl-3-propyl-1-octanol
2. a) b) c)

d) CH3-O-CH3


i) j)

3. Methane is a low molecular weight alkane, very non-polar, and is expected to be a gas. Methanol has a polar alcohol (-OH) functional group and can undergo hydrogen bonding so it remains in the liquid state longer.


5. a) same b) isomers c) isomers d) isomers e) isomers


8. CH2=CH2 + H2O

KMnO4

Intramolecular

10. CH3CH=CH2 + H2O

H2SO4
Intermolecular

CH3CH2CH2-OH


CH3CH2CH2-O-CH2CH2CH3

+ H2O

12.

H2SO4

H2SO4

13. CH2=CH2 + H2O (Intramolecular)

CH3CH2-O-CH2CH3 + H2O (Intermolecular)


H2SO4

+ H2O (Intramolecular)
(Intermolecular)
H2SO4
+ H2O

H2SO4

13.

(Intramolecular)



+ H2O

H2SO4

+ H2O

(Intermolecular)

KMnO4

KMnO4

KMnO4

14.

No Reaction
16.

KMnO4


b) CH3CH2OH

KMnO4

e)

f) + KMnO4



KMnO4

H2SO4

Intramolecular
H2SO4

Intermolecular

r) CH3CH2OH CH2=CH2 + H2O

CH3CH2–O–CH2CH3 + H2O


t) CH2=CHCH3 + H2O


KMnO4
u) (CH3)3C—OH No Reaction

H2SO4


v) CH3OH CH3–O–CH3 + H2O
KMnO4
y)

Δ
z) CH3CH2—O—CH3 + O2 CO2 + H2O

19.

H2SO4

If intramolecular
e)

If intermolecular

KMnO4

f)
KMnO4

k) No Reaction
Intermolecular

+ H2O


m)

H2SO4


Intramolecular

KMnO4
q) No Reaction
Intermolecular

only
H2SO4

r)

There is usually more than one correct answer for the following:



20.
Δ

b) CH3CH=CH2 + H2O


KMnO4

c)

H2SO4


Intermolecular

d)

KMnO4


e) CH3CH2CH2CH2OH


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