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Chapter 10,11,14 Homework

Chapter 10

10.1 Classify 2,3-dimethylbutan-2-ol.


a) 0o alcohol
b) 1o alcohol
c) 2o alcohol
d) 3o alcohol

10.2 Give the common name for (CH3)3CCH2OH.


a) tert-Pentyl alcohol
b) tert-Butyl alcohol
c) Isopentyl alcohol
d) Isobutyl alcohol
e) Neopentyl alcohol

10.3
a) Butan-1-ol
b) Butan-2-ol
c) Butane-1,2-diol
d) Butane-1,2-ol

10.4
a) 1-Propylphenol
b) 2-Propylphenol
c) 3-Propylphenol
d) 4-Propylphenol

10.5 Give the name of the alcohol that is in beer and wine.
a) Methanol
b) Ethanol
c) Propan-2-ol
d) Propan-1-ol

10.6 Give the common use for ethane-1,2-diol.


a) Drinking alcohol
b) Rubbing alcohol
c) Vinegar
d) Antifreeze

10.7
a) NaCH2CH2CH2OH
b) CH3CH(Na)CH2OH
c) CH3CH2CH(Na)OH
d) CH3CH2CH2ONa
10.8
a) CH3CH2CH2OH
b) CH3CH2OCH3
c) CH3CH2OH
d) CH3CH2OMgBr

10.9 Identify the alcohol formed when a Grignard reagent adds to a ketone.
a) 0o alcohol
b) 1o alcohol
c) 2o alcohol
d) 3o alcohol

10.10
a) 3-Methylpentan-3-ol
b) 2-Methylbutan-2-ol
c) 2-Methylbutan-3-ol
d) 2-Methylpentan-3-ol

10.11
a) 3-Methylpentan-3-ol + methanol
b) 2-Methylbutan-2-ol + ethanol
c) 2-Methylbutan-3-ol + methanol
d) 2-Methylpentan-3-ol + ethanol

10.12
a) CH3CH2CH(OH)CH3
b) CH3CH2OH
c) CH3CH2CH2OH
d) CH3CH2CH2CH2OH

10.13 Give the reason why Grignard reactions must have dry glassware.
a) Grignard reagents react vigorously and irreversibly with water.
b) Magnesium dissolves in water.
c) The alkyl halide dissolves in water.
d) Grignard reagents do not react with water.

10.14 Identify the compounds that sodium borohydride reduces.


a) Aldehydes and ketones
b) Esters and carboxylic acids
c) Aldehydes, ketones, esters, and carboxylic acids
d) Alkenes and alkynes

10.15
a) CH2=CHCH(OH)CH2COOH
b) CH3CH2CH(OH)CH2COOH
c) CH2=CHCH(OH)CH2CH2OH
d) CH3CH2CH(OH)CH2CH2OH

10.16
a) Aldehydes and ketones
b) Esters and carboxylic acids
c) Aldehydes, ketones, esters, and carboxylic acids
d) Alkenes and alkynes

10.17
a) CH2=CHCH(OH)CH2COOH
b) CH3CH2CH(OH)CH2COOH
c) CH2=CHCH(OH)CH2CH2OH
d) CH3CH2CH(OH)CH2CH2OH

10.18 Identify the compounds that hydrogen and Raney nickel reduces.
a) Aldehydes and ketones
b) Esters and carboxylic acids
c) Aldehydes, ketones, esters, and carboxylic acids
d) Alkenes and alkynes
e) Aldehydes, ketones, alkenes, and alkynes

10.19
a) CH2=CHCH(OH)CH2COOH
b) CH3CH2CH(OH)CH2COOH
c) CH2=CHCH(OH)CH2CH2OH
d) CH3CH2CH(OH)CH2CH2OH

10.20
a) CH3CH2CH2SOH
b) CH3CH2CH2SO2H
c) CH3CH2CH2SO3H
d) CH3CH2CH2SO4H
Chapter 11

11.1
a) (CH3)2CHOH
b) (CH3)2C=O
c) CH3CH2COOH
d) No reaction

11.2
a) CH3COOH
b) CH3CH2COOH
c) CH3CH2CHO
d) No reaction

11.3
a) CH3COOH
b) CH3CH2COOH
c) CH3CH2CHO
d) No reaction

11.4
a) (CH3)3COH
b) (CH3)2C=O
c) CH2=C(CH3)2
d) No reaction

11.5 Identify the reagent that is notused to oxidize a primary alcohol to a carboxylic acid.
a) HNO3
b) PCC
c) Na2Cr2O7, H2SO4
d) CrO3, H2SO4

11.6
a) CH3CH2CH2OTs
b) CH3CH2CH2OCl
c) CH3CH2CH2Cl
d) CH3CH2CH2Ts

11.7
a) CH3CH2CH2OTs
b) CH3CH2CH2OCl
c) CH3CH2CH2Cl
d) CH3CH2CH2Ts
e) CH3CH2CH3
11.8
a) (CH3)2CHBr
b) CH3CH2Br
c) CH3CH2CH2Br
d) BrCH2CH2CH2Br

11.9
a) (CH3)2CHCH2Br
b) (CH3)3CBr
c) CH3CH2CH2CH2Br
d) BrCH2CH2CH2CH2Br

11.10
a) CH3CH2CH2OPBr3
b) CH3CH2CH2OBr
c) CH3CH2CH2Br
d) CH3CH2CH2PBr2

11.11
a) CH3CH2CH2OSCl2
b) CH3CH2CH2Cl
c) CH3CH2CH2OCl
d) CH3CH2CH2SO2H

11.12
a) But-1-ene
b) cis-But-2-ene
c) trans-But-2-ene
d) All of the above

11.13
a) 140 °C gives dipropyl ether.
b) 180 °C gives dipropyl ether.
c) 140 °C gives dipropyl ether + propene.
d) 180 °C gives dipropyl ether + propene.

11.14
a) 2,3-Dimethyl-3-hydroxybutan-2-one
b) 2,3-Dimethylbutane-2,3-dione
c) 2,3-Dimethylbutane-2,3-diol
d) 3,3-Dimethylbutan-2-one

11.15
a) Two aldehydes
b) Aldehyde + ketone
c) Two ketones
d) Ketone + carboxylic acid
e) Two carboxylic acids

11.16
a) CH3CH2COOCH3
b) CH3COOCH2CH3
c) CH3CH2COOCH2CH3
d) CH3COOCH3

11.17
a) CH3OSO3H
b) CH3OSO3CH3
c) CH3OSO2CH3
d) CH3OSO2H

11.18
a) CH3ONO2
b) CH3NO2
c) CH3ONO
d) CH3OH

11.19
a) CH3OPO(OH)2
b) (CH3O)2PO(OH)
c) (CH3O)3PO
d) CH3OCH3

11.20
a) CH3CH3
b) CH3CH2OCH3
c) CH3OCH3
d) CH3CH2OCH2CH3
Chapter 14

14.1
a) Ethyl propyl ether
b) Diethyl ether
c) Ethyl isopropyl ether
d) Pentyl ether

14.2
a) 1-Ethoxypropane
b) 2-Ethoxypropane
c) 1-Propoxyethane
d) 2-Propoxyethane

14.3
a) 12-Crown-4
b) 15-Crown-5
c) 18-Crown-6
d) 21-Crown-7

14.4
a) Oxetane
b) Furan
c) Pyran
d) Dioxane
e) Epoxide

14.5
a) Oxetane
b) Furan
c) Pyran
d) Dioxane
e) Epoxide

14.6
a) CH3CH2OCl
b) CH3CH2Cl
c) CH3CH3
d) CH3CH2OCH3

14.7
a) (CH3)2C(OCH3)CH3
b) (CH3)2CHCH2OCH3
c) (CH3)3CCH3
d) (CH3)2C(OCH2CH3)CH3
14.8
a) CH3CH=CH2
b) (CH3)2CHOCH(CH3)2
c) CH3CH2CH2OCH2CH2CH3
d) CH3CH2CH2OCH(CH3)2

14.9
a) CH3CH=CH2
b) (CH3)2CHOCH(CH3)2
c) CH3CH2CH2OCH2CH2CH3
d) CH3CH2CH2OCH(CH3)2

14.10
a) C6H5OH + CH3CH2Br
b) C6H5Br + CH3CH2OH
c) C6H5OH + CH3CH2OH
d) C6H5Br + CH3CH2Br

14.11
a) CH3CH2CH2Br + CH3CH2OH
b) CH3CH2CH2OH + CH3CH2Br
c) CH3CH2CH2OH + CH3CH2OH
d) CH3CH2CH2Br + CH3CH2Br

14.12
a) Dimethyl sulfide
b) Dimethyl thiol
c) Dimethyl sulfone
d) Dimethyl sulfoxide

14.13
a) Dimethyl sulfide
b) Dimethyl thiol
c) Dimethyl sulfone
d) Dimethyl sulfoxide

14.14
a) Dimethyl sulfide
b) Dimethyl thiol
c) Dimethyl sulfone
d) Dimethyl sulfoxide

14.15
a) Ethyl methyl sulfide
b) Ethyl methyl thiol
c) Ethyl methyl sulfone
d) Ethyl methyl sulfoxide

14.16
a) Alcohol + carboxylic acid
b) Two alcohols
c) Two carboxylic acids
d) Epoxide + carboxylic acid
e) Two epoxides

14.17
a) Epoxide
b) Alcohol
c) Alkyl halide
d) Ether
e) Carboxylic acid

14.18
a) HOCH2CH(OH)CH3
b) HOCH2CH(OCH2CH3)CH3
c) CH3CH2OCH2CH(OH)CH3
d) CH3CH2OCH2CH(OCH2CH3)CH3

14.19
a) HOCH2CH(OH)CH3
b) HOCH2CH(OCH2CH3)CH3
c) CH3CH2OCH2CH(OH)CH3
d) CH3CH2OCH2CH(OCH2CH3)CH3

14.20
a) HOCH2CH(OH)CH3
b) HOCH2CH(CH2CH3)CH3
c) CH3CH2CH2CH(OH)CH3
d) CH3CH2CH2CH(CH2CH3)CH3

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