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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.
Class Activity 15
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
/ decreased / same
/ decreased / same
/ decreased / same
/ decreased / same
/ decreased / same
/ decreased / same
Class Activity 15
Class Activity 15
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).
(c).
(d).
reduction using LiAlH4