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Problem and Key of Amines

This document contains a 12-question problem set on amines from a Chapter 24 chemistry textbook. The questions cover classifying and naming amines, predicting products of amine reactions, drawing reaction mechanisms for amine syntheses and conversions, and comparing properties of amines like basicity and boiling points. Students are asked to classify, name, draw structures, provide mechanisms, predict products, rank compounds, and show multi-step synthetic routes involving reactions like reductive amination, Gabriel synthesis, and Hoffman elimination.

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vania kristiahadi
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133 views

Problem and Key of Amines

This document contains a 12-question problem set on amines from a Chapter 24 chemistry textbook. The questions cover classifying and naming amines, predicting products of amine reactions, drawing reaction mechanisms for amine syntheses and conversions, and comparing properties of amines like basicity and boiling points. Students are asked to classify, name, draw structures, provide mechanisms, predict products, rank compounds, and show multi-step synthetic routes involving reactions like reductive amination, Gabriel synthesis, and Hoffman elimination.

Uploaded by

vania kristiahadi
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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Chemistry

234
Chapter 24 - Problem Set
1) Classify each amine as primary, secondary, or tertiary.

N N
NH 2
H N
H

2) Give the IUPAC name for each compound shown below.
Br NH 2 N

Cl
NH N
H

O O

HO
N Br
NH 2

N
N






3) The structure of pseudoephedrine is shown below. Show a valid reaction for the conversion of
pseudoephedrine to the hydrochloride salt. Be sure to include both the required reagent(s) and the
product. (3 points)
OH

Ph
HN




Page 1 of 4
Chem. 234 – Chapter 24 Problem Set
4) The amine below can be prepared by reducing an amide, a nitro compound, or a nitrile. Show the
structure for each of these three potential starting materials.


NH 2

amide nitro compound nitrile




5) Provide a full arrow pushing mechanism for the reaction shown below. Note: You do not need to
show any arrows for step 2 (Ag2O, H2O).
1. CH 3I (xs)
2. Ag2O, H 2O
+ N(CH 3)3 + AgI + H 2O
NH 3. Heat















6) Predict the major product for each reaction below.

O NaBH 3(CN)
Ph NH 2 +
Ph MeOH

H2
Ph NO 2
Pd/C

1. CH 3I (xs)
NH
2. Ag2O, H 2O
3. Heat

CH 3I (xs)
NH 2

HBr
NH 2

N 1. LAH
2. H 2O
Page 2 of 4
Chem. 234 – Chapter 24 Problem Set
7) Rank the compounds in each set below in order of increasing basicity.
NH 2
NH 2
NH 2

O



O

NH 2 N N
H H



8) Show how cyclohexylpropylamine can be prepared via reductive amination starting with ammonia.
Show the mechanism for the one of the reductive amination steps. *Note: Order does not matter.
You can make either cyclohexylamine or propyl amine first.
















9) Show how butylamine can be prepared via the Gabriel Amine Synthesis.















Page 3 of 4
Chem. 234 – Chapter 24 Problem Set
10)Show the products following a series of two Hoffman eliminations of the cyclic amine below.

N
H







11)Rank the compounds below in order of increasing boiling point.

N NH 2 NH 2





12)Write the complete electron pushing mechanism for the reductive amination of benzaldehyde and
methylamine.

Page 4 of 4

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