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CHM207 Tutorial

This document provides a tutorial on alkyl halides, which are organic compounds containing carbon-halogen bonds. It includes questions testing understanding of structures, IUPAC names, classifications as primary/secondary/tertiary, reagents for reactions, drawing reaction schemes, predicting products, and mechanisms of substitution and elimination reactions of alkyl halides.

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93 views

CHM207 Tutorial

This document provides a tutorial on alkyl halides, which are organic compounds containing carbon-halogen bonds. It includes questions testing understanding of structures, IUPAC names, classifications as primary/secondary/tertiary, reagents for reactions, drawing reaction schemes, predicting products, and mechanisms of substitution and elimination reactions of alkyl halides.

Uploaded by

it's mia
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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CHM207 (ORGANIC CHEMISTRY)

TUTORIAL 5
CHAPTER 5: ALKYL HALIDES

1. Give the structures of the following compounds:

a. 1,2-Dichlorocyclopentene
b. 3-Chloro-4-phenylheptane
c. 1,2-Dibromo-3-methylpentane
d. 1-Bromo-2,2-dimethylpropane
e. trans-1,4-Diiodocyclohexane
f. 1-Bromo-3-methylhexane
g. 3-Bromo-2,4-dimethylpentane

2. Give systematic (IUPAC) names for the following compounds.

a. Br

b. Cl

CH3

c. Cl CH3

d. (CH3)2CHCH2Br

e. Cl

Cl

3. Classify the following compounds as primary, secondary or tertiary alkyl halides.

a. CH3CH2CHFCH(CH3)2
b. (CH3)2CHCH2Cl
c. CH3CH2CHBrCH3
d. (CH3)3CBr
e. I

1
CHM207 (ORGANIC CHEMISTRY)

4. Give the reagents for the reactions below:

a. CH3CH=CHCH3 CH3CH=CHCH2Cl

b. CH3CH=CHCH3 CH3CHCHCH3
Br Br

c. Cl Cl

Cl

d.

Br

Cl
e.

5. Draw the structural formula of compounds A-E to complete the reaction scheme
below.

Compound A + HCl Compound B + KCl

CH3CH2NH2 KCN

CH3CH2OH + Na Compound C + CH3CH2CH2Cl Compound D + NaCl

KOH (aq)/reflux

Compound E + KCl

6. Give the product(s) for the following reactions:

a. 2CH3CH2CH2Cl + 2Na

b. (CH3)2CHCH2CH2CI + KOH (aq) reflux

c.
reflux
+ KOH/alcohol
Br
2
CHM207 (ORGANIC CHEMISTRY)

7. Predict the compound in each pair that will undergo the SN2 reaction faster:

a. or
Br
Br

b. or
Cl I

c.
Cl or CH2Cl

8. Predict the elimination product(s) (E1 mechanism) of the following compounds.


Label the major and minor products. Some intermediates need to undergo
rearrangement to obtain stable carbocation.

a. CH3CH(Br)CH2CH2CH3 c. (CH3)3C CH CH3


Br

b. Cl d. Cl
CH3
CH3CCH2CH3
CH3

9. Write the complete SN2 mechanism for the reaction between hydroxide ion and 1-
bromopropane.

10. Write the complete SN1 mechanism for the reaction between water and 2-bromo-
2-methylpropane.

11. Complete these nucleophilic substitution reaction by show all electron pairs on
both the nucleophile and the leaving group. Write a rate expression for this
reaction.

Br CH3ONa ?
CH3OH

12. Show the E2 mechanism for the following chemical reactions.

a. HO- + CH3CHBrCH3 CH2=CHCH3 + H2O + Br-

b. CH3CH2O- + (CH3)3Cl CH2=C(CH3)2 + CH3CH2OH + Cl-

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