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CHEM1102 2014-J-8 June 2014 • Complete the following ..., Exams of Stereochemistry

Montana State UniversityStereochemistry

Draw the structure of the organic product(s) formed when each of the following compounds is treated with 4 M sodium hydroxide.

Typology: Exams

2021/2022

Uploaded on 09/12/2022

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CHEM1102 2014-J-8 June 2014
• Complete the following table. Make sure you give the name of the starting material
where indicated.
Marks
4
STARTING MATERIAL
REAGENTS/
CONDITIONS
STRUCTURAL
FORMULA(S) OF MAJOR
ORGANIC PRODUCT(S)
(CH3)2NH
hot 3 M NaOH
Cl
O
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe
pff
pf12
pf13
pf14
pf15
pf16
pf17
pf18
pf19
pf1a
pf1b
pf1c
pf1d
pf1e
pf1f
pf20
pf21
pf22
pf23
pf24
pf25
pf26
pf27

Partial preview of the text

Download CHEM1102 2014-J-8 June 2014 • Complete the following ... and more Exams Stereochemistry in PDF only on Docsity!

CHEM1102 2014 - J- 8 June 2014

  • Complete the following table. Make sure you give the name of the starting material where indicated.

Marks 4

STARTING MATERIAL

REAGENTS/

CONDITIONS

STRUCTURAL

FORMULA(S) OF MAJOR

ORGANIC PRODUCT(S)

(CH 3 ) 2 NH

hot 3 M NaOH

Cl

O

CHEM1102 2014 - J- 9 June 2014

  • Methylphenidate, also known as Ritalin, is a psychostimulant drug approved for the treatment of attention-deficit disorder. Identify all stereogenic (chiral) centres in methylphenidate by clearly marking each with an asterisk (*) on the structure below.

Marks 7

Using one stereogenic centre you have identified, draw the ( R )-configuration of that centre.

How many stereoisomers are there of methylphenidate? Describe the relationships between these isomers.

4 isomers: there are 2 pairs of enantiomers: Each isomer has 1 enantiomer and 2 diastereoisomers

Give the products formed when methylphenidate is hydrolysed with 4 M HCl.

methylphenidate

CHEM1102 2014 - N- 8 November 2014

  • Complete the following table.

Marks 1

STARTING MATERIAL REAGENTS/CONDITIONS

THE MAJOR

ORGANIC PRODUCT(S)

SOCl 2

O

Cl

CHEM1102 2014 - N- 9 November 2014

  • Draw the structure of the organic product(s) formed when each of the following compounds is treated with 4 M sodium hydroxide. The first reaction requires heating.

Compound Organic products

O

O

H 2 N

N

OH O

O

CHEM1102 2013 - J- 14 June 2013

  • Below is the reaction between an acid chloride and water to give a carboxylic acid. Provide curly arrows for this mechanism and draw the structures of the two intermediates on the pathway.

Marks 6

Indicate the hybridisation of the two oxygen atoms in the starting materials.

acid chloride: sp^2 water: sp^3

THE REMAINDER OF THIS PAGE IS FOR ROUGH WORKING ONLY.

CHEM1102 2013 - N- 8 November 2013

  • Complete the following table.

Marks 1

STARTING MATERIAL

REAGENTS/

CONDITIONS

CONSTITUTIONAL

FORMULA(S) OF MAJOR

ORGANIC PRODUCT(S)

SOCl 2

CHEM11 02 2013 - N- 12 November 2013

  • Consider the three compounds shown below.

Arrange these compounds in order of increasing acidity. Explain your reasoning.

Marks 3

Ethanol is the weakest acid as its conjugate base is not resonance stabilised. Phenol is a stronger acid as its conjugate base is resonance stabilised – the negative charge can be delocalised into the aromatic ring as shown below.

There is even greater resonance stabilisation for the acetate ion (the conjugate base of acetic acid), as the negative charge is delocalised onto the electronegative oxygen atoms (as opposed to the carbon atoms in the case of phenol).

CHEM11 02 2013 - N- 13 November 2013

  • The incomplete mechanism for the reaction of acetyl chloride with hydroxide ions is shown below. The reaction occurs in three steps. In each step complete the mechanism by adding curly arrows to indicate the bond changes taking place.

Marks 3

CHEM1102 2012 - J- 10 June 2012

  • Complete the following table. If there is no reaction, write “NR”. Show any relevant stereochemistry.

Marks 7

STARTING MATERIAL

REAGENTS/

CONDITIONS

CONSTITUTIONAL

FORMULA(S) OF MAJOR

ORGANIC PRODUCT(S)

Cr 2 O 72 –^ / H+

H+^ catalyst / heat

(CH 3 ) 2 NH / heat

CHEM1102 2012 - J- 12 June 2012

  • Consider the following molecule ( M ) isolated from a natural source.

H 2 N

N COOH

NH 2

H

O

Marks 6

Give the products when molecule ( M ) is hydrolysed by heating it with 6 M HCl. Make sure you show the products in their correct ionisation states.

( M )

CHEM1102 2012 - N- 10 November 2012

  • Complete the following table.

Marks 1

STARTING MATERIAL

REAGENTS/

CONDITIONS

CONSTITUTIONAL

FORMULA(S) OF MAJOR

ORGANIC PRODUCT(S)

SOCl 2

CHEM1102 2012 - N- 11 November 2012

  • Draw the structure of the organic product(s) formed when each of the following compounds is treated with 4 M sodium hydroxide. The first two reactions proceed at room temperature; the last one requires heating.

Marks 4

Compound Organic Product(s)

THE REMAINDER OF THIS PAGE IS FOR ROUGH WORKING ONLY.

CHEM1102 2010-N-9 November 2010

  • Complete the following table. Marks 2

STARTING MATERIAL

REAGENTS/

CONDITIONS

CONSTITUTIONAL

FORMULA(S) OF MAJOR

ORGANIC PRODUCT(S)

OH

O

SOCl (^2)

O

O

Cl

O

H / H 2 O / heat

CHEM1102 2010-N-10 November 2010

  • The following is a nucleophilic addition-elimination reaction between ammonia and an acid anhydride. Provide curly arrows needed for the mechanism, and draw the structures of the two intermediates on this pathway.

Marks 5