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Class Activity 15

Oxidation and Reduction

Class Activity 15
Oxidation and Reduction
Model 1: Reduction Reactions
Reducing Reagents [Red]:
Strong Reducing Reagent: LiAlH4
Weak Reducing Reagent: NaBH4

Questions:
1. For the reduction reactions, from left to right, shown in Model 1:
(a). The number of C-H bonds for Eq. A is (circle one) increased / decreased / same
(b). The number of C-H bonds for Eq. B is (circle one) increased / decreased / same
(c). The number of C-H bonds for Eq. C is (circle one) increased / decreased / same
2. For the reduction reactions, from left to right, shown in Model 1:
(a). The number of C-O bonds for Eq. A is (circle one) increased / decreased / same
(b). The number of C-O bonds for Eq. B is (circle one) increased / decreased / same
(c). The number of C-O bonds for Eq. C is (circle one) increased / decreased / same
3. Using the above information, reduction of organic compounds can be described as an
increase in the bonds to __H__ or a decrease in the bonds to __O__.
4. Consider the reduction reaction CH3CHBrCHBrCH3 CH3CH=CHCH3.
(a). The number of C-H bonds is (circle one) increased / decreased / same
(b). The number of C-Br bonds is (circle one) increased / decreased / same
(c). Compare the effect of halogens to that of oxygen (#2 above) in a reduction reaction.
Halogens are classified in (circle one) the same / differently with regards to reduction
compared to oxygen.
(d). Explain why this reaction is a reduction reaction. Since the number of bonds to halogen
Br has been decreased, this is a reduction reaction.
5. Consider the reaction RCHBrCH3 RCH=CH2 + HBr
(a). The number of C-H bonds is (circle one) increased / decreased / same
(b). The number of C-Br bonds is (circle one) increased / decreased / same
(c). Would this reaction be considered a reduction reaction? (circle one) yes / no
Explain. Although C-Br bonds have been decreased, C-H bonds have also been
decreased, so it is not considered a reduction reaction.

by Suzanne Ruder, PhD

Class Activity 15

Oxidation and Reduction

6. Reducing reagents can be classified as strong or weak as shown in Model 1. Compare the
starting carbonyl compound to the product in each of the following reactions:
Carbonyl
LiAlH4 Reductions
NaBH4 Reductions
Acids
RCO2H + LiAlH4 RCH2OH
RCO2H + NaBH4 RCO2H
Esters
RCO2CH3 + LiAlH4 RCH2OH
RCO2CH3 + NaBH4 RCO2CH3
Ketones
RCOR + LiAlH4 RCH(OH)R
RCOR + NaBH4 RCH(OH)R
Aldehydes
RCHO + LiAlH4 RCH2OH
RCHO + NaBH4 RCH2OH
(a). Which carbonyls undergo reduction with LiAlH4? (circle) acid / ester / ketone / aldehyde
(b). Which carbonyls undergo reduction with NaBH4? (circle) acid / ester / ketone / aldehyde
(c). Are any of the reducing reagents unable to reduce some carbonyl compounds?
(circle one) yes / no
If so, list the reagent and the carbonyl group(s) that is not reduced by the reagent.
NaBH4 does not reduce acids or esters.
(d). Once everyone in your group agrees on the above concepts, determine the reducing
reagents that will accomplish the following transformations:

Model 2: Oxidation
Oxidizing Reagents [Ox]:
Strong Oxidizing Reagents:
Na2Cr2O7, H2SO4 or
KMnO4
Weak Oxidizing Reagents:
CrO3-Py-HCl (PCC) or
(COCl)2, Et3N, DMSO (Swern)

Questions:
7. For the oxidation reactions, from left to right, shown in Model 2:
(a). The number of C-H bonds for Eq. D is (circle one) increased
(b). The number of C-H bonds for Eq. E is (circle one) increased
(c). The number of C-H bonds for Eq. F is (circle one) increased
8. For the oxidation reactions, from left to right, shown in Model 2:
(a). The number of C-O bonds for Eq. D is (circle one) increased
(b). The number of C-O bonds for Eq. E is (circle one) increased
(c). The number of C-O bonds for Eq. F is (circle one) increased

by Suzanne Ruder, PhD

/ decreased / same
/ decreased / same
/ decreased / same
/ decreased / same
/ decreased / same
/ decreased / same

Class Activity 15

Oxidation and Reduction

9. Using the above information, oxidation of organic compounds can be described as an


increase in the bonds to _O___ or a decrease in the bonds to __H___.
10. For the oxidation reaction CH3CH=CHCH3 CH3CHBrCHBrCH3
(a). The number of C-H bonds is (circle one) increased / decreased / same
(b). The number of C-Br bonds is (circle one) increased / decreased / same
(c). Compare the effect of halogens to that of oxygen (#8 above) in an oxidation reaction.
Halogens are classified in (circle one) the same / differently with regards to oxidation
compared to oxygen.
11. Oxidizing reagents can be classified as strong or weak as shown in Model 2. Compare the
starting compound to the product in each of the following reactions:
Compound
Strong [Ox] Reagents
Weak [Ox] Reagents
1 ROH
RCH2OH + [Ox] RCO2H
RCH2OH + [Ox] RCHO
2 ROH
R2CHOH + [Ox] RCOR
R2CHOH + [Ox] RCOR
3 ROH
R3COH + [Ox] R3COH
R3COH + [Ox] R3COH
Aldehydes
RCHO + [Ox] RCO2H
RCHO + [Ox] RCHO
(a). Strong [Ox] convert primary alcohols to ___carboxylic acids_______.
(b). Weak [Ox] convert primary alcohols to _______aldehydes_______.
(c). Strong [Ox] convert secondary alcohols to _____ketones________. Compare the
oxidation of secondary alcohols with weak [Ox]. Are there any differences? (circle one)
Yes or no. Explain. .The same product is obtained (ketone) with either reagent.
(d). Strong [Ox] convert aldehydes to _____ carboxylic acids _______. Compare the
oxidation of aldehydes with weak [Ox]. Are there any differences? (circle one) Yes or
no. Explain. Weak oxidizing reagents do not oxidize aldehydes to carboxylic acids
(e). Are there any compounds not oxidized by either strong or weak [Ox]? (circle one) yes /
no. If so what compounds? Tertiary alcohols are not oxidized by any of the reagents
listed.
(f). Once everyone in your group agrees on the above concepts, choose the reagents that
will accomplish the following transformations:

Reflection: on a separate sheet of paper.


As a group, write three concepts your group has learned from this activity and the one most
important unanswered question about this activity that remains with your group. Turn this in
before leaving class.

by Suzanne Ruder, PhD

Class Activity 15

Oxidation and Reduction

Additional Questions:
12. Classify each of the following reactions as either oxidation, reduction or neither.
(a).

oxidation
(b).
oxidation
(c).
reduction
(d).

neither
13. Shown below are some important cellular processes. Identify whether they are oxidation or
reduction reactions.
(a).

oxidation
(b).

reduction
14. Determine whether the reactions below are oxidation or reduction. List all of the reagents
that will accomplish the transformations shown.
(a).
oxidation using strong [Ox] like
Na2Cr2O7/H2SO4 or KMnO4

(b).

reduction using LiAlH4 or NaBH4

(c).

oxidation using weak [Ox] like


PCC or Swern

(d).
reduction using LiAlH4

by Suzanne Ruder, PhD